The Supreme Court Paladins

After showcasing the hall of shame it’s time for the good justices, and this is a completely serious post. These are my favorites:

1. Louis Brandeis (1916-1939) (R-D)
2. Neil Gorsuch (2017-present) (R)
3. Robert Jackson (1941-1954) (D)
4. John Marshall Harlan (1877-1911) (R)
5. Elena Kagan (2010-present) (D)
6. Hugo Black (1937-1971) (D)
7. Stephen Field (1863-1897) (D)
8. Antonin Scalia (1986-2016) (R)
9. Oliver Wendell Holmes (1902-1932) (R)

Five Republicans and five Democrats (Brandeis was both), so it’s some consolation that I’m party-blind — just as these justices do an admirable job of leaving party at the door when they sit the bench. Readers may wonder about certain omissions, like John Marshall (1801-1835) and Earl Warren (1953-1969), but those two were highly activist. I’m not saying they were bad justices, and it’s undeniable that their activism landed positive results. Marshall established the process of judicial review, and Warren’s court democratized the Bill of Rights. In each case, it was less out of an activist desire to remake the law, and more to remedy the effects of governmental paralysis. Still, I believe they’re overrated. They were strong leaders, but not the best judicial thinkers, and they had primarily political rather than legal backgrounds.

1. Louis Brandeis (1916-1939). Appointed by Woodrow Wilson. The best justice was appointed by the very worst president, though that’s not surprising. Justices prove time and time again they are not beholden to the executive. Neil Gorsuch (at my #2 slot) is another case in point. Readers may be surprised in any case to see Louis Brandeis topping my list, since his reputation is one of a living constitutionalist, but that reputation is misleading. It’s true that he believed the Constitution had to be interpreted in light of present realities but he wasn’t activist. The biographer Jeffery Rosen calls him a “living originalist” — somewhere between the hard-core originalists and the living constitutionalists — which is about right, though I think more the former in effect if the latter in appearance. Brandeis always insisted on judicial restraint; any “activism” on his part was just a matter of taking constitutional principles to their logical conclusions, or clarifying them in a period of technological change. His starting point was always the framers — the values they meant to protect, especially speech and privacy. Some aspects of his jurisprudence have been embraced by liberals like Ruth Ginsburg and Elena Kagan (who have called themselves originalists), and other aspects by conservatives like Antonin Scalia and Clarence Thomas (the hard-core originalists). Both camps agree that he was a model of jurisprudence and didn’t dissent (as some judges and justices do) when the court’s ruling produced results that he found personally displeasing. Quite the contrary.

There are six particular reasons that Brandeis earns the top slot on my list:

(1) He developed a fact-based evidence approach to arguing cases, instead of just relying on legal theory. He began this as a lawyer, years before his appointment to the Supreme Court, and the method came to be known as the “Brandeis Brief”. It’s now a staple of constitutional law. With the Brandeis Brief, the courts were brought into the solid orbit of facts. From 1907 to 1914 Brandeis defended people who were overworked in the name of “the freedom to contract” (established by the terrible Lochner v. New York ruling in 1905), advocating statues that prescribed maximum hours of labor and minimum decency of wages. In 1908 he famously appeared before the Supreme Court in Muller v. Oregon, representing the state in defending women workers. He had two pages of legal arguments, and over a hundred pages of statistics, sociological data, historical facts, and expert opinion arguing that women were unable to work for more than ten hours at a time. Astonishingly — considering this was the Lochner era of 1905-1937 — he won his case: the Court ruled that states could limit the working hours of women; it was constitutional under the Fourteenth Amendment, in the interest of protecting their health. Facts and evidence-based arguments impressed the court, and those are the kind of arguments that would impress Brandeis when he became a SCOTUS justice in 1916.

(2) He did more for the cause of free speech than any other justice in American history (on which see below).

(3) He advocated strenuously (if in vain) for the cause of privacy, which he believed was inherent in American law, and should apply to electronic surveillance as much as to physical trespass (on which see below).

(4) He believed in preserving federalism, which meant preserving the autonomy of the states. State legislatures had to be able to make laws suited to varied and changing needs; their laws should be struck down only when they interfered with basic freedoms (on which see below).

(5) He was acutely aware of the dangers of big business. He defended personal and economic liberty and opposed centralization in business or government (on which see below).

(6) He was objective about FDR’s New Deal legislation. Although a foe of strong centralized federal government like FDR’s, Brandeis supported the constitutional validity of most of the New Deal legislation — though not indiscriminately. He joined, for example, the Court’s ruling which held the National Industrial Recovery Act of 1933 to be unconstitutional, as well as the ruling of Humphrey’s Executor v. United States (1935), which said that the president may not remove any appointee to an independent regulatory agency except for reasons that Congress has provided by law. And he wrote the ruling for Louisville Joint Stock Land Bank v. Radford (1935), which invalidated the Frazier–Lemke Act because it deprived the bank of private property without just compensation, in violation of the Fifth Amendment. Brandeis thus showed himself to be objective on a huge issue that was very hard to be objective about.

Brandeis, in other words, might be called a Jeffersonian libertarian who espoused the ideals of small government and local democracy while applying those ideals to uphold state regulations that tamed the excesses of big business and monopolies. (I wish Brandeis could be unleashed today on corporations like Facebook and Youtube.) Like Jefferson, he believed that the greatest threat to our constitutional liberties were uneducated citizens, and that democracy could not survive ignorance.

— At his best: Judicial Deference to State Experimentation. In New State Ice v. Liebmann (1932), Brandeis dissented to the 7-2 ruling that struck down a state law (Oklahoma’s) that required manufacturers to get licenses from a state commission before opening a new business. Brandeis didn’t like the government intrusiveness, but he believed that state and local responses to economic challenges had to be encouraged, unless they violated the Constitution. The majority said that the license requirements for ice manufacturers violated the Due Process Clause. Brandeis (correctly, I believe) thought the majority were reaching. Likewise, in Liggett v. Lee (1933), Brandeis dissented to the 6-3 ruling that struck down a state law (Florida’s) that aimed to protect small independently owned businesses in competition with out-of-state chain stores by taxing the chain stories with a license fee. In that case, he was livid that the Court had prevented states like Florida from trying to protect local businesses from out-of-state rivals. In his view, the ruling failed to defer to legislative fact-finding, not to mention that it offended the principles of federalism (states rights) and judicial restraint. Also, Brandeis was a Jeffersonian, not a Hamiltonian, and knew the dangers of big corporations. He showed, using fact-based evidence, that when states ignore safeguards against corporate power, the result are institutions that have the power to challenge and/or dominate the states themselves. Florida’s tax was a constitutional good, going beyond merely protecting a handful of small businesses from out of state competition. The tax protected the viability of American ideals like equal opportunity, economic self-sufficiency, and personal liberty. The Court had eradicated that tax because it (supposedly) violated the Equal Protection Clause. Giving big businesses an added advantage in the name of “equal protection” is Orwellian, and Brandeis said as much in his dissent.
— Free Speech. Brandeis believed that speech could be restricted only if (a) it threatened to result in harm that was both imminent and serious, and (b) there was no time for deliberation to defuse the danger. He was way ahead of his time. It would take more than 40 years, in Brandenburg v. Ohio (1969), for the Court to establish the “incitement to violence” provision: that in order to lose First Amendment protection, speech must be “directed to inciting or producing imminent lawless action and is likely to incite or produce such action” (which is why hate speech is protected; people shouldn’t be arrested for speaking hatefully, but try telling that to the modern woke). In the ’20s the victories for free speech were more foundational. Brandeis became the famous defender of the First Amendment in Gitlow v. New York (1925) — a landmark ruling that made free speech a state right, for the very first time, as much as a federal one. But the Court upheld Gitlow’s conviction anyway, 7-2, on grounds that his speech directly advocated the unlawful overthrow of the government. Oliver Wendell Holmes dissented, and Brandeis joined him, on grounds that indefinite advocacy of overthrowing government should be protected speech; they rightly insisted that threats had to be imminent to fall outside First Amendment protection. Two years later, in Whitney v. California (1927), Brandeis wrote a concurrence to the 9-0 ruling, which remains to this day the greatest defense of free speech ever written by SCOTUS justice, explaining why the solution to bad speech is more speech, or counter-speech, or better speech, but not censorship: “If there be time to expose through discussion the falsehood and fallacies, to avert the evil by the process of education, the remedy to be applied is more speech, not enforced silence.”
— Privacy. In Olmstead v. United States (1928), the Supreme Court dealt with its first case of electronic searches. The feds were tapping phones to enforce Prohibition, Olmstead was a bootlegger generating more than $2 million a year from illegal booze and he protested that the wire taps that busted him violated the Fourth Amendment. (Actually the wire taps were illegal under Washington state law.) In a 5-4 ruling, Chief Justice Taft said that Olmstead’s rights hadn’t been violated: the Fourth Amendment only prohibited searches or seizures accompanied by physical trespass, and the feds hadn’t trespassed on Olmstead’s property when they placed the wiretaps on the phone lines near his house. Brandeis found that inadequate in the 20th century. Phone conversations often contained more sensitive information than sealed letters. He wrote: “At the time of the adoption of the Fourth and Fifth Amendments, force and violence were the only means by which the government could compel self-incrimination. Thus, the protections offered by these Amendments were necessarily limited to address only imaginable forms of such force and violence. However, with the technological advances, the government has received the ability to invade privacy in more subtle ways.” Brandeis’s wisdom wouldn’t prevail until exactly 90 years later, in Carpenter v. United States (2018), when the Court ruled that cell phone data had Fourth Amendment protection. Even here however, the ruling was narrow, applying only to cell phone data, and not to other forms of third-party data (like bank records, etc.) which to this day police can search without warrants. The Court has yet to fully embrace Brandeis’ view that all forms of electronic surveillance without warrants are unconstitutional. This is a classic case where hyper-literal originalism fails. I certainly don’t think Brandeis was a judicial activist for trying to apply the Fourth Amendment in an era where spying can occur without physical trespass.

— At his worst: Free Speech, Part 2. Brandeis hadn’t always been a free speech purist. In Schenck v. United States, Frohwerk v. United States, and Debs v. United States — all delivered in March 1919 — Brandeis joined a unanimous court in upholding Woodrow Wilson’s tyranny during World War I, ruling that criticizing U.S. involvement the war is a criminal offense, and that criticizing the draft is a criminal offense. The people in these cases were sentenced to years in prison for simply exercising their free speech rights. However, two of the nine justices — Brandeis and Oliver Wendell Holmes (see #9 below) — redeemed themselves months later, in the case of Abrams v. United States, which also sent people to prison for speaking against U.S. involvement in the war. This case was delivered in November, but this time the ruling was 7-2: Brandeis and Holmes had had a change of heart, repenting of their errors. They became the strongest champions of free speech from then on.
— Eugenics. In Buck v. Bell (1927), the Supreme Court made one of its worst rulings of all time, ruling that it was constitutional to sterilize people against their will if they were unfit or mentally disabled. Brandeis didn’t write anything for the opinion but he did join it. (To be fair, eugenics was widely accepted between 1907-1939, and Harvard University itself was promoting it, so we can hardly fault presidents like Harding and justices like Holmes and Brandeis too much for following what the best scholars and experts were saying on the subject.)

Best Brandeis quote: “The most important political office is that of the private citizen.”

2. Neil Gorsuch (2017-present). Appointed by Donald Trump. The best justice on today’s court — and in my opinion, the second best justice of all time — is an originalist whose objectivity rarely cracks; a consistently conservative justice, even when his legal opinions happen to align him with liberal politics. Some examples: in United States v. Haymond (2019), he wrote for the 5-4 majority (himself and the four liberals), overturning the lower court’s denial of a trial by jury to a man convicted a second time of carrying child pornography. (Rightfully: a new crime demands a new trial, no matter how despicable the offense. That’s a conservative legal position, though a liberal social point of view.) He joined the liberals against the conservatives to protect immigrants from being deported in Sessions v. Dimaya (2018), striking down a statute about “aggravated felonies” that was unconstitutionally vague. He even joined the liberals on a gun issue in United States v. Davis (2019), in which the Trump administration was trying to over-punish two criminal defendants. Gorsuch, however, has two Achilles’ heels: labor law and religious influence in the public sector. When it comes to church-state issues, he could take a few lessons from Robert Jackson (see #3 below). But on whole, Neil Gorsuch is the justice I’ve been waiting for all my life.

— At his best: Indian Rights. In Washington State Department of Licensing v. Cougar Den Inc. (2019), Gorsuch joined the four liberals to rule that a fuel wholesaler owned by a member of the Yakama Indian Nation was exempt from paying state fuel taxes for using public highways because the Yakama Treaty of 1855 granted members of the Nation the right “to travel upon all public highways” and preempted its obligation to pay the tax. Only two months later, Gorsuch and the liberals ruled again in favor of Indians: In Herrera v. Wyoming (2019), saying (a) that statehood does not imply termination of reserved hunting rights for Indians, and (b) that establishment of a national forest does not render an area occupied — thereby upholding Indian treaties. Liberal politics, but conservative law. Then, in McGirt v. Oklahoma (2020), Gorsuch joined the liberals in ruling that prosecution of crimes by Native Americans on Indian reservations is under the jurisdiction of the tribal courts and federal judiciary, not the state courts. He wrote the opinion for McGirt, stating categorically: “We are asked whether the land these treaties promised remains an Indian reservation for purposes of federal criminal law. Because Congress has not said otherwise, we hold the government to its word.” McGirt, however, left open the question about crimes committed by non-Natives against Natives on Indian Reservations. The issue was decided in Oklahoma v. Castro-Huerta (2022), with a conservative majority (Barrett having replaced Ginsburg) ruling against Indian jurisdiction. Gorsuch wrote a furious dissent, joined by the three liberals: “Where this Court once stood firm, today it wilts. Where our predecessors refused to participate in one State’s unlawful power grab at the expense of the Cherokee, today’s Court accedes to another.” It’s a proper dissent — and to stress the point, a conservative one — which appeals to the landmark ruling of Worcester v. Georgia (1823), which has persisted for over 200 years: native tribes retain their sovereignty unless and until Congress ordains otherwise.
— Wedding Cakes for Gay Couples. In Masterpiece Cakeshop, Ltd. v. Colorado Civil Rights Commission (2018), the majority (7-2) upheld the right of a private business owner (Jack Philipps) to refuse to design one of his products in a particular way (i.e. the right of a baker to refuse to make a wedding cake that celebrates gay marriage). But the ruling was on narrow grounds, and it stated that it could not provide a precedent for future scenarios like this. In his concurrence, Gorsuch did better than that, taking the case on its merits and arguing that Philipps was justified period in refusing designs for cakes, the substantive point being that private business owners cannot be compelled to create a product that they object to on religious or moral grounds. Stunningly, the Colorado Civil Rights Commission had already acknowledged this very principle in its own treatment of three bakers who refused to bake cakes with anti-gay messages on them. The Commission, said Gorsuch, should have found in the Philipps’ favor, just as it had found in favor for the other three bakers. All four bakers were in the same situation. The three bakers refused to sell a cake that denigrated same-sex marriage, just as Jack Philipps refused to sell a cake celebrating same-sex marriage. Most crucially: The atheist bakers in the first case were happy to sell to persons of Christian faith, just as the conservative Christian baker in the second case was happy to sell to gay people. In both cases, it was the kind of cake, not the kind of customer, that mattered to the bakers. Gorsuch’s reasoning was absolutely correct. Business owners cannot be compelled to artistic design, only to provide equal access to their products. Whatever they do create, they must sell impartially and without discrimination. But they aren’t obligated to create something in the first place that goes against their religious or moral convictions. Gorsuch’s concurrence should have been expanded on and embraced as the majority opinion.
— Separation of Powers. In Gundy v. United States (2019), the question was: could the attorney general both declare that a pre-SORNA sex offender was required to register under SORNA (Sex Offender Registration and Notification Act) and then prosecute him for having failed to register? This placed the power to make a law and the power to enforce it in the same hands, which is a classic violation of the separation of powers. The ruling was 5-4 in favor of a Super-Attorney-General, and Gorsuch wrote the dissent, rightly arguing: “It would be easy enough to let this case go. After all, sex offenders are one of the most disfavored groups in our society. But the rule that prevents Congress from giving the executive carte blanche to write laws for sex offenders is the same rule that protects everyone else.” Indeed it’s crazy to let the chief prosecutor write his own criminal code — in other words, to write the criminal law for those he’s going to prosecute — as it gives him way too much power over half a million people.
— Gay & Transgendered Rights. In Bostock v. Clayton County (2020), Gorsuch wrote for the 6-3 majority (himself, four liberals, and Roberts) ruling that an employer who fires an individual merely for being gay or transgender violates Title VII of the Civil Rights Act of 1964. Gorsuch argued that Title VII prohibits employers from discriminating against any individual “because of such individual’s race, color, religion, sex, or national origin”. His entire reasoning was value-free: Discrimination on the basis of one’s sexual orientation or transgender status is by definition sex discrimination, because in both types of discrimination, an employer must consider the employee’s sex — in other words, the employee’s biological marker of being a man or a woman — before the employer can identify the employee as homosexual (one who is sexually attracted to someone of the same sex) or transgender (one who is identifying with the other sex). Without the employer’s consideration of the employee’s sex, it would be impossible for that employer to discriminate against the employee on the basis of sexual orientation or transgender status. “Sexual orientation” and “transgender” cannot be defined, let alone understood, without explicit reference to sex. It doesn’t matter that gays and transgendered aren’t explicitly named in the Act, or that they weren’t intended at the time of writing — anymore than it matters that interracial marriage wasn’t intended to be protected by the Equal Protection Clause when written in 1868. Bostock is a solid example of value-free orignalism and gives lie to the myth that orignalism yields outcomes mostly favorable to conservative politics.

— At his worst: Prayer in Public Schools. In Kennedy v. Bremerton School District (2022), Gorsuch, for whatever bizarre reason, decided that a football coach’s prayer at midfield was private speech, not governmental, and therefore he had the right to kneel and pray without any interference from the school officials. But the coach’s speech was obviously not private. Even though it was after the game, he was still acting in his role as a public employee. He was engaging in a prominent public display of religiosity, and the school officials had every right to tell him that such behavior is inappropriate. Now school officials don’t have that right anymore, thanks to Gorsuch.
— Labor Laws and Unions. In Epic Systems Corp. v. Lewis (2018), the Court upheld the validity of employment contracts in which employees give up their right to collective litigation against their employer. Gorsuch penned the decision, first framing the issue as a straightforward matter of resolving a potential contradiction between two federal statutes: “It is this Court’s duty to interpret Congress’s statutes as a harmonious whole.” But it’s not the Supreme Court’s duty to do that, but rather to examine each statue on its own constitutional merits. Gorsuch is usually better than that. The result is that without class action options, employees will be less able to sue, and employers less accountable to their employees. Gorsuch also joined the terrible ruling of Janus v. American Federation of State, County, and Municipal Employees (2018), which decreed that the extraction of agency fees from non-consenting public-sector employees violates the First Amendment — which it does not. Just because a person disagrees with the politics of a union doesn’t mean that being forced to pay an agency fee violates his or her free expression. It keeps the person from being a freeloader and reaping benefits that others pay for.

Best Gorsuch quote: “Originalism is the worst form of constitutional interpretation, except for all the others.”

3. Robert Jackson (1941-1954). Appointed by Franklin Delano Roosevelt. First of all, this man could write. Take this, on the subject of free speech: “In this field every person must be his own watchman for truth, because the forefathers did not trust any government to separate the true from the false for us.” Or this: “Compulsory unification of opinion achieves only the unanimity of the graveyard.” His legacy, aside from prosecuting Nazis at the Nuremberg trials, was a consistent defense of free expression and maintaining a high wall of separation between church and state. It’s interesting that he and Hugo Black (see #6 below) hated each other so much (especially when Black shafted Jackson out of a chief justice nomination), when they were very similar in their approach to jurisprudence; strangely, they each dropped the ball on free speech on a singular occasion: Jackson came down hard on communist assemblers (for which Black rightly blasted him) and Black came down on public school students wearing armbands to protest the Vietnam war. No justice is perfect. We could certainly use a Robert Jackson on today’s court, where religion is being increasingly defended in the wrong places, even by first-rate justices like Neil Gorsuch.

— At his best: Free Expression. In Virginia State Board of Education v. Barnette (1943), Jackson wrote for the majority, striking down requirements in public schools to salute the flag and recite the Pledge of Allegiance. It’s one of his most famous opinions.
— Separation of Church and State. In Everson v. Board of Education (1947), he dissented when the 5-4 majority ruled that a New Jersey law providing public payment of transportation costs to and from Catholic schools did not violate the Establishment Clause. Jackson said rightly that it did violate the clause. Likewise he dissented in Zorach v. Clauson (1952), when the 6-3 majority said that a public school district could allow students to leave school for part of the day to receive religious instruction, as long as the instruction took place away from the school and didn’t have public funding. Jackson rejected even those conditions, maintaining a firm church-state division, and concluded: “Today’s judgment will be more interesting to students of psychology and of the judicial processes than to students of constitutional law.”
— Presidential Power. In Youngstown Sheet & Tube v. Sawyer (1952), he wrote a concurring opinion about presidential power which is one of the most widely cited opinions in SCOTUS history. The background involved Truman seizing control of steel production facilities during a strike to keep the productions running. Hugo Black wrote for the 6-3 majority, denying Truman the right to do this, but it was Jackson’s concurrence that outlined the now-famous three-tiered test for presidential power as follows: (1) cases in which the President is acting with express or implied authority from Congress, in which case “his authority is at its maximum, for it includes all that he possesses in his own right plus all that Congress can delegate”; (2) cases in which Congress has thus far been silent, in which case “his authority can derive support from congressional inertia, indifference or quiescence”; (3) cases in which the president is defying congressional orders, in which case “his power is at its lowest ebb, and the Court can sustain his actions only by disabling the Congress from acting upon the subject”.
— Internment of Japanese Americans. In the appalling case of Korematsu v. United States (1943), Jackson was one of three dissenters, arguing against the use of executive power to deprive citizens of their basic rights. Not even national security warrants that, especially when there’s not a shred of evidence against those being detained. The internment of Japanese Americans, said Jackson, was terrible and would set a precedent for war-time racial discrimination.
— Desegregation. In Brown v. Board of Education (1954), the Court voted unanimously to overturn the “separate but equal” doctrine of Plessy v. Ferguson (1896). The court ruled that separate facilities were inherently unequal, according to the Equal Protection Clause of the Fourteenth Amendment. Earl Warren wrote the opinion, and there were no dissents or concurrences. But Jackson did write a concurring draft before he was suddenly hospitalized by the end of March. He was released on May 17, when the ruling of Brown was delivered, so that he could be present for the important 9-0 decision. His unpublished concurrence wasn’t made available until 1986, during the scandal of William Rehnquist’s confirmation hearing. As a law clerk under the Warren court, Rehnquist had written privately to Jackson, urging that Plessy should be upheld. When questioned about it during his confirmation hearings, he lied, claiming that it was Jackson who said this. In fact Jackson believed that Plessy should be overturned but he struggled to find a constitutional argument for it. His unpublished concurrence stated that (1) he was “predisposed to the conclusion that segregation has outlived whatever justification it may have had”; (2) yet he found no evidence that segregation was prohibited, particularly since states that had ratified the Fourteenth Amendment had segregated schools at the time; (3) the enforcement of desegregation should ideally be left to Congress, since the “courts have no power to enforce general declarations of law”, but in this case the Court must act because “our representative system has failed”; (4) changed conditions in America, along with the importance of a public education, required the Court to strike down the “separate but equal” doctrine in public education. In other words, while Jackson couldn’t legally justify Warren’s ruling in Brown, he did so on the basis of social imperatives, which was unusual for him. My own feeling is that Warren’s opinion was legally justified (on the basis of the Equal Protection Clause, just as he argued), and that Jackson was second-guessing himself too much. He did the right thing, if by the wrong road, but he certainly wasn’t a Plessy supporter as Rehnquist claimed (who was projecting his own prejudices onto Jackson in order to secure his chief justice confirmation).
— Procedural due process. Jackson was a staunch defender of protecting people from overreach by government agencies. Before depriving someone of life, liberty, or property, due process is required — an unbiased trial, being notified in advance, the right to present evidence and call witnesses, to know the opposing evidence, to cross-examine, to have legal counsel, etc. It was largely for this reason that Truman appointed Jackson to prosecute Nazi war criminals at Nuremberg, granting him a leave of absence from the court between 1945-46. In this, Jackson presented a good face of America to the world: even the lowest Nazi war criminals deserve due process.

— At his worst: Communist sympathizers. In Dennis v. United States (1951), the Court ruled 6-2 that Eugene Dennis had “conspired and organized for the overthrow and destruction of the United States government by force and violence”. This was a load of horseshit, and it’s amazing that Jackson joined this ruling. Hugo Black was one of the two dissenters (see #6 below, for the full citation), blasting the majority as fools — for Dennis and his friends hadn’t been engaged (or even charged) with any immediate overt acts of any kind. All they’d been doing was assembling and talking about communist writings that teach the overthrow of the U.S. government. This was a failure of SCOTUS to uphold basic free speech rights (something Jackson was usually good about), but then this was the McCarthy era.

Best Jackson quote: “Compulsory unification of opinion achieves only the unanimity of the graveyard.”

4. John Marshall Harlan (1877-1911). Appointed by Rutherford Hayes. Not to be confused with his grandson John Marshall Harlan II (who served on the Court from 1955-1971, and wasn’t a very good justice), the first John Marshall Harlan was a former slave holder and proponent of slavery. He swore during the Civil War that he would resign from the army if Lincoln signed the Emancipation Proclamation, but later repented (in 1871) and became a fervent critic of slavery and prejudice. He was the first justice to earn a law degree, and when he joined the Court he swiftly earned his reputation as “The Great Dissenter”, especially in cases that restricted civil liberties. It was a dark period on the Court when many constitutional provisions were dead letters. Harlan advocated (in vain) that the Bill of Rights be incorporated into the Due Process Clause of the Fourteenth Amendment (ratified in 1868), and thus applied to state and local governments. He insisted (in vain) that the residents of U.S. Territories in the Philippines, Puerto Rico, and Guam be entitled to the full Constitutional rights of American citizens. And he dissented (in vain) against a pack of justices who ruled that racially segregated public facilities were fine, as long as they were “equal”. He was certainly no activist and paid proper deference to state legislatures. But he used common sense on a court filled with judicial blindness. I rank Harlan at #4, but he’s actually the justice I respect most for standing alone (very often) against the scorn of his colleagues.

— At his best: Civil Rights. In The Civil Rights Cases (1883) — five separate cases brought by African Americans suffering racial discrimination — the issue at hand was the Civil Rights Act of 1875. This congressional law outlawed acts of racial discrimination, but the court ruled 8-1 that the Fourteenth Amendment only prohibited state acts of discrimination, not acts committed by private individuals and privately owned businesses. Harlan argued that to allow acts of discrimination in the private sphere created a badge of slavery that marks minorities as inferior, thus violating the Reconstruction Amendments (13th, 14th, and 15th). (The Court actually acknowledged that the Thirteenth Amendment does apply to private actors, but only to prohibit people from owning slaves, not from engaging in general discriminatory behavior.) Harlan’s dissent fell on deaf ears.
— Incorporating the Bill of Rights. In Hurtado v. California (1884), a 7-1 majority ruled that state governments were not obligated to use grand juries in criminal prosecutions. Harlan was the lone dissenter, in his first major push for incorporating the Bill of Rights (in this case the Fifth Amendment) into the states, and not just the federal government.
— Racial Segregation. Most famously, he dissented in Plessy v. Ferguson (1896), in which the 7-1 majority ruled that segregation laws don’t violate the Constitution as long as the facilities for each race are equal in quality. As Harlan pointed out, this doctrine of “separate but equal” is an oxymoron:

“Everyone knows that the statute in question had its origin in the purpose, not so much to exclude white people from railroad cars occupied by blacks, as to exclude colored people from coaches occupied by or assigned to white persons. In view of the constitution, there is in this country no superior, dominant, ruling class of citizens. There is no caste here. Our constitution is color-blind, and neither knows nor tolerates classes among citizens. In respect of civil rights, all citizens are equal before the law. The humblest is the peer of the most powerful.”

His “color-blind” comment became famous, but it would take almost six decades for Brown v. Board of Education (1954) to strike down segregation and call out the “separate but equal” doctrine for what it was (see #3 above, under Robert Jackson). Harlan also dissented in Berea College v. Kentucky (1908), which ruled that states could prohibit private schools from admitting both black and white students.
— Colonialism. In Downes v. Bidwell (1901), the Court ruled 5-4 that the Constitution doesn’t necessarily apply to American territories like Puerto Rico, Hawaii (before it was a state), the Philippines, and Guam, and Congress has jurisdiction to create laws within territories that would not be allowed by the Constitution. Harlan was incensed, writing: “It will be an evil day for American liberty if the theory of a government outside the Supreme Law of the Land finds lodging in our Constitutional Jurisprudence. No higher duty rests upon this court than to exert its full authority to prevent all violation of the principles of the Constitution.” Harlan was as anti-imperialist as he was anti-racist.
— Voting Rights. In Giles v. Harris (1903), the Court refused (in a 5-4 ruling) to assist African Americans in Alabama who were being denied the right, and it was none other than Oliver Wendell Holmes (see #9 below) who wrote the ruling. The case involved Alabama’s efforts to limit voting to those who owned property and could pass a literacy test. Giles (suing for more than 5000 black citizens) asked the Court to add the names of many black citizens to the voting rolls, but Holmes denied the request because the voting regime was fraudulent, and it was not for the Court to add names to a fraudulent system. In other words, because the system is unfair, Holmes wouldn’t make it more fair by adding names to an unfair system. Further, because the case was brought in equity, rather than as a constitutional challenge, Holmes believed it would not be proper to invalidate it (even though he believed it was invalid). Harlan dissented, believing that the Court did have jurisdiction to invalidate the law, and said that Holmes and the majority were copping out.

— At his worst: The Chinese. Harlan wasn’t perfect. If he was enlightened with respect to Africans and other races, he had deep prejudices against the Chinese. In United States v. Wong Kim Ark (1898), the Court ruled 7-2 that people of Chinese descent born in the United States were citizens by birth. Chief Justice Fuller and Harlan dissented, and Harlan actually said: “There is a race so different from our own that we do not permit those belonging to it to become citizens of the United States. I allude to the Chinese race.” Like the chief justice, Harlan believed there were dangers of having large numbers of Chinese immigrants in the U.S.

Best Harlan quote: “Our Constitution is color-blind, and neither knows nor tolerates classes among citizens.”

5. Elena Kagan (2010-present). Appointed by Barack Obama. She’s the best liberal to sit the court in the past 40 years, with no axes to grind and a broad view of the law. She has allied with conservatives on the court more frequently than other liberals, which means nothing in itself, but may just be an indication (and it is) that she interprets the law as a judiciary and not a tribal ideologue. For example, she joined the five conservatives in favor of Jack Phillips, the baker who had refused to make a cake for a gay couple’s wedding, whereas Ginsburg and Sotomayor dissented. She joined the conservatives in allowing a forty-foot-tall cross commemorating soldiers who died in World War I to remain on public land in Maryland. Ginsburg and Sotomayor found the Christian symbolism to be overwhelming and a violation of the establishment clause of the Constitution. Kagan recognized that the cross was acceptable because it dated back to the 1920s and belonged to a venerable line of World War I memorials, whose particular religious significance had faded over time. Kagan’s intellect is so sharp that it led Harvard law professor Mark Tushnet to predict in 2013, that someday the Supreme Court might be formally led by Chief Justice Roberts, but intellectually led by Justice Kagan. Of course, that was before Neil Gorsuch joined the court. Both he and Kagan are the best of today’s court, and they both rank on my list of the best justices of all time. Like Gorsuch, Kagan is especially good in her dissents and writes with a razor when the situation calls for it.

— At her best: Union Agency Fees. In Janus v. American Federation of State, County, and Municipal Employees (2018), Kagan went on the full offensive in her dissent against the attack on unions: “There is no sugarcoating today’s opinion. The majority overthrows a decision entrenched in this nation’s law — and in its economic life — for over 40 years. As a result, it prevents the American people, acting through their state and local officials, from making important choices about workplace governance. And it does so by weaponizing the First Amendment, in a way that unleashes judges, now and in the future, to intervene in economic and regulatory policy. The majority has overruled Abood for no exceptional or special reason, but because it never liked the decision. Speech is everywhere — a part of every human activity (employment, health care, securities trading, you name it). For that reason, almost all economic and regulatory policy affects or touches speech. The First Amendment was meant not to undermine but to protect democratic governance, including over the role of public-sector unions.” She was right. Janus is one of the most poorly reasoned SCOTUS decisions in the 21st century.
— Gerrymandering. In Rucho v. Common Cause (2019), the conservative majority (led by Chief Justice Roberts) ruled that partisan gerrymandering claims present political questions beyond the reach of the federal courts. (Gerrymandering is the manipulation of electoral boundaries so as to favor one party or class of citizens over another.) Kagan made another trenchant dissent: “The partisan gerrymanders in these cases deprived citizens of the most fundamental of their constitutional rights: the rights to participate equally in the political process, to join with others to advance political beliefs, and to choose their political representatives. In so doing, the partisan gerrymanders here debased and dishonored our democracy, turning upside-down the core American idea that all governmental power derives from the people.” Rucho most certainly involved a constitutional question; Roberts (and the other conservatives) were just throwing up their hands because they didn’t want to get them dirty.
— Deportation. Kagan is just as good in writing for a majority. In Sessions v. Dimaya (2018), she wrote for the liberals and Gorsuch, striking down an immigration statute that defined “aggravated felonies” as unconstitutionally vague. The Immigration and Nationality Act (INA) classified these categories, and legal immigrants convicted of those crimes were getting unjustly shafted with deportation.
— Free Speech. In Iancu v. Brunetti (2019), Kagan wrote for a 6-3 victory in striking down a law banning vulgar or scandalous trademarks. Applying that rule, the government had denied a trademark for the name “FUCT,” concluding that it was phonetically equivalent to the past tense or past participle of “fuck”. Kagan argued that the trademark law’s restriction violates the First Amendment because “it disfavors certain ideas”. Note the dissenters in what should have been a 9-0 slam dunk: Roberts, who said that while the First Amendment protects freedom of speech, “it does not require the government to give aid and comfort to those using obscene, vulgar, and profane modes of expression”; and liberals Sotomayor and Breyer, to their shame. So in this very interesting case, four conservatives and two liberals upheld the First Amendment, while one conservative and two liberals did not. This weight of opinion lends credence to the claim that the stronger threats to free speech come more from the left than the right. I’m glad that it was a liberal justice who penned the decision.

— At her worst: No objectionable rulings or opinions stand out in particular. I’ve been routinely impressed with Kagan.

Best Kagan quote: “My politics would be, must be, have to be, completely separate from my judgment.”

6. Hugo Black (1937-1971). Appointed by Franklin Delano Roosevelt. Like John Marshall Harlan (#4), Hugo Black represents a 180-degree turn from an ugly past, in his case being a member of the Ku Klux Klan. People joked that as a young man he wore white robes and scared black people, and as an older man he wore black robes and scared white people. Despite his inclinations to uphold FDR’s New Deal regulations and expand the federal government, Black defied the easy categorization of a liberal. He was in many ways a judiciary conservative, and some scholars say that he was the most politically liberal originalist who ever sat on the Court. He believed in judicial restraint, and insisted that judges rely on the intent of the framers as well as the “plain meaning” of the Constitution’s words. He fervently opposed the idea that justices should be activists, social engineers, or rewriters of the Constitution. This often goes unnoticed: before the arch-conservative Scalia there was the flaming liberal Black, both judiciary conservatives. The Stone-Age Robert Bork later wrote in admiration: “Justice Black came to have significantly more respect for the limits of the Constitution than Justice Douglas and the other leading members of the Warren majorities ever showed.” So while Black was often on the same page of opinion with Warren and his activist liberals, he usually arrived at those opinions by a safer road.

— At his best: Free expression. Black was a free speech absolutist, maintaining that Congress could not make any laws that abridged the First Amendment. In Dennis v. United States (1951), he was one of two dissenters against the majority who ruled that a member of the Communist Party USA had “conspired and organized for the overthrow and destruction of the government by force and violence”. This was pure horseshit (but it was the McCarthy era, so no surprise), and Black dissented as follows: “The petitioners were not charged with overt acts of any kind designed to overthrow the Government. They were not even charged with saying anything or writing anything designed to overthrow the Government. The charge was that they agreed to assemble and to talk and publish certain ideas at a later date. The indictment is that they conspired to organize the Communist Party and to use speech or newspapers and other publications in the future to teach and advocate the forcible overthrow of the Government. No matter how it is worded, this is a virulent form of prior censorship of speech and press, which the First Amendment forbids.”
— Separation of church and state. Black believed in a fairly high wall of separation between church and state. He dissented (along with Robert Jackson, see #3 above) in Zorach v. Clauson (1952), when the 6-3 majority said that a public school district could allow students to leave school for part of the day to receive religious instruction, as long as the instruction took place away from the school and didn’t have public funding (meaningless qualifiers that didn’t fool Black or Jackson for a moment). And in Engel v. Vitale (1962), he wrote for the majority, ruling against teacher-led prayer in public school classrooms. However, his wall of separation wasn’t quite as high as Jackson’s (see further below).
— Incorporating the Bill of Rights. Black crusaded on this point, believing (like John Marshall Harlan decades before, see #4 above) that the entirety of the federal Bill of Rights was applicable to the states. This was a hard sell, however, given the precedent of Barron v. Baltimore (1833), which had ruled that the Bill of Rights was binding only upon the federal government. According to Black, the Fourteenth Amendment, ratified in 1868, “incorporated” the Bill of Rights to make it binding on the states. Especially the Privileges or Immunities Clause, which says, “No state shall make or enforce any law which shall abridge the privileges or immunities of citizens of the United States.” Black insisted that “privileges or immunities” encompassed the rights mentioned in the first eight amendments to the Constitution. He never achieved the support of other justices for this view, and from the ’30s to the ’50s it was pretty much just the First Amendment that was binding on the states (thanks to Gitlow v. New York (1925)). His crusade paid off in the long run, though. In the ’60s under Earl Warren, the Court made almost all guarantees of the Bill of Rights binding on the states. Gideon v. Wainright (1963) did it for the Sixth Amendment, Mapp v. Ohio (1961) did it for the Fourth Amendment. Malloy v. Hogan (1964) did it for the Fifth Amendment. If the Court rejected Black’s theory of total incorporation, the end result was mighty damn close to what Black had crusaded for. Today, the only parts of the first eight amendments that haven’t been extended to the states are the Third and Seventh Amendments, the grand jury clause of the Fifth Amendment, and the Eighth Amendment’s protection against excessive bail. I count Black’s crusade a success in this regard, and a very important one.
— Voting Rights. Black was an adamant proponent of the “one man, one vote” principle, believing in electoral reforms of universal suffrage, proportional representation, and the elimination of plural voting and gerrymandering. He wrote for the 7-2 majority in Wesberry v. Sanders (1964), holding that the Constitution required congressional districts in any state to be approximately equal in population. He also joined the 8-1 ruling in Reynolds v. Sims (1964), which extended the same requirement to state legislative districts on the basis of the Equal Protection Clause.

— At his worst: Internment of Japanese Americans. The greatest stain on Black’s career was his opinion for the 6-3 majority in Korematsu v. United States (1943), which ruled that the internment of Japanese Americans during World War II was permissible. Robert Jackson was one of three dissenters (see #3 above), rightly arguing against the use of executive power to deprive citizens of their basic rights. Not even national security warrants that, especially when there’s no evidence against those being detained. It’s astonishing that a civil libertarian like Black wrote an opinion like this, but it goes to show how far even the best people fall in times of war.
— Free expression, Part 2. Black was a free speech purist — insisting that the First Amendment is “wholly beyond the reach of federal power to abridge” — but he also took a narrow view of what constituted speech. He didn’t consider conduct like flag-burning to be protected. So he wasn’t quite the absolutist he thought he was, and in Tinker v. Des Moines (1969), he dissented against the 7-2 majority, which ruled that in order to regulate speech in the classroom, public school officials had to have a constitutionally valid reason — in other words, that the conduct would “materially and substantially interfere with the requirements of appropriate discipline in the operation of the school”. In this case, the five students in Des Moines were simply wearing black armbands in protest of American involvement in the Vietnam War. The Court rightly ruled in favor of them. But Black saw this conduct as falling into the category of “disruptive symbolic speech” (like flag burning), and dissented, saying that such conduct was beyond the purview of the First Amendment.
— Separation of church and state, Part 2. As stated above, Black believed strongly in separation between church and state, and in most cases ruled accordingly, but on one significant occasion he made an exception that undermined his own logic. Writing for the majority in Everson v. Board of Education (1947), he ruled that a New Jersey law providing public payment of transportation costs to and from Catholic schools didn’t violate the Establishment Clause. (Jackson correctly insisted that it did violate the clause; see #3 above). It’s worth citing Black in full:

“The ‘establishment of religion’ clause of the First Amendment means at least this: Neither a state nor the Federal Government can set up a church. Neither can pass laws which aid one religion, aid all religions or prefer one religion over another. Neither can force nor influence a person to go to or to remain away from church against his will or force him to profess a belief or disbelief in any religion. No person can be punished for entertaining or professing religious beliefs or disbeliefs, for church attendance or non-attendance. No tax in any amount, large or small, can be levied to support any religious activities or institutions, whatever they may be called, or whatever form they may adopt to teach or practice religion. Neither a state nor the Federal Government can, openly or secretly, participate in the affairs of any religious organizations or groups and vice versa. In the words of Jefferson, the clause against establishment of religion by law was intended to erect ‘a wall of separation between Church and State.’ That wall must be kept high and impregnable.”

The four dissenters, led by Jackson, agreed with this as spelled out (as who could not?), while pointing out that these very principles led to the invalidation of the New Jersey law that Black was defending. For obviously the funds used here were raised by taxation. Parents paid money to send their kids to private schools and the funds raised by taxation were being used to reimburse them. This goes beyond merely helping the children get to school. It helps them get the very thing they are sent to private school for: religious education. It’s funny how Black got this so wrong.
— Substantive due process. Black rejected the idea that courts can establish rights protecting one from government interference, if those rights aren’t specifically mentioned in the Constitution. Most justices (rightly) believe that such protections come from the due process clauses of the Fifth and Fourteenth amendments. Black believed this interpretation was unjustifiably broad, and in his dissent to the 7-2 ruling of Griswold v. Connecticut (1965), he said that because the Constitution doesn’t mention privacy in any of its provisions, the majority had no basis to strike down Connecticut’s Comstock Law which made the sale of contraceptives illegal: “I like my privacy as well as the next one, but I am nevertheless compelled to admit that government has a right to invade it unless prohibited by some specific constitutional provision.” That’s a terrible dissent.

Best Black quote: “A union of government and religion tends to destroy government and degrade religion.”

Honorable mentions

The last three are honorables. There’s much I admire about them, but their faults are deep enough to nearly balance the positives (in the cases of Field and Scalia) or the legacy is somewhat overrated (in the case of Holmes).

7. Stephen Field (1863-1897). Appointed by Abraham Lincoln. His most important opinions were dissents, so ringing and profound that they showed the real potential in bucking against the majority. Written well, dissents appealed to the wisdom of a future day, when later rulings might correct present errors. Field famously dissented in The Slaughterhouse Cases (1897), which ruled that the Due Process Clause of the Fourteenth Amendment protected only privileges and immunities pertaining to federal citizenship, not state citizenship. Thanks to that ruling, a Louisiana law that put a thousand butchers out of business was upheld. Field said that the Court’s ruling effectively rendered the Fourteenth Amendment a “vain and idle enactment”. In this he was like John Marshall Harlan (see #4 above) and Hugo Black (#6 above), calling for the extension of basic rights to the state governments as much as the federal. They would all be vindicated by the end of the 1960s. But if Field was stellar on the subject of due process, he was overboard on the subject of freedom to contract. His laissez-faire economics (for which I have sympathies) was too laissez-faire and helped make possible the Lochner era of 1905-1937. Best quote: “The assault on capital is the stepping-stone to others, larger and more sweeping, till our political contests will become a war of the poor against the rich.”

8. Antonin Scalia (1986-2016). Appointed by Ronald Reagan. He was the catalyst for a much needed return to originalism and textualism that had been lost during the Warren years, and he was the first justice who made me think hard about the role of the Supreme Court when I began dabbling in the ’90s. I found a transcript of the oral arguments of Texas v. Johnson (1989) — the famous flag burning case — and read it many times over, struck by how Scalia ended up joining hands with the liberals to make a 5-4 ruling that it was okay to burn the American flag. He would later write opinions like Brown v. Entertainment Merchants Association (2011), ruling that violent video games have First Amendment protection, and the government cannot enforce parental consent when it comes to video games. Also surprisingly, he dissented in Hamdi v. Rumsfeld (2004), a terrible ruling that upheld the detainment of Yaser Hamdi, an American citizen, as an enemy combatant (Scalia said that Hamdi had to be either charged with a crime or freed right away). I wish Scalia had applied his originalism more consistently, and that he hadn’t made awful rulings favoring big corporations, but I can’t deny his important contributions. And when a liberal like Elena Kagan (see #5 above) acknowledges that “we’re all originalists now, thanks to Scalia”… well, that’s saying quite a lot. Best quote: “The judge who always likes the results he reaches is a bad judge.”

9. Oliver Wendell Holmes (1902-1932). Appointed by Theodore Roosevelt. Holmes is a giant, and for me he looms larger than John Marshall and Earl Warren who were too activist. For Holmes, judicial restraint was imperative, so much that he said: “If my fellow citizens want to go to Hell, then I will help them. It’s my job.” That might be my favorite quote from any SCOTUS justice. And yet there’s something about Holmes’ stature that seems overblown. I don’t know. As I comb through his writings, no opinion on its own suggests a towering greatness. It’s rather the cumulative force of his opinions, and his insane bestseller The Common Law (1881), that gave him that. I can’t leave him off the list with a clean conscience, so he’s the last honorable mention. Best quote: “If my fellow citizens want to go to Hell, then I will help them. It’s my job.”