Anthony Kennedy Was Never Really a Friend to Liberals

This is another entry of our column from the hosts of the legal podcast Mic Dicta breaking down issues knocking around the US legal system.

Confirmed to the Supreme Court in 1988, Kennedy was a compromise choice by President Ronald Reagan after his first two nominees failed. The first, Robert Bork, was voted down for the good reason of being an extremist loon; the second, Douglas Ginsburg, withdrew his own name from consideration for the hilarious reason that he smoked pot sometimes in his 20s and it was scandalous. At the time, nobody doubted that Kennedy was a conservative, but at least he was completely uninteresting.

Somehow, though, due to changes in personnel and the leftward shift of Justice David Souter, Kennedy often found himself alone in the nominal center of a court lurching rightward. Though the four on either side of him shifted, he stayed sitting in the middle. This position gave him a rare power: The tug of war for his soul from both sides required constant appeals to his idiosyncratic sense of personal morality and, apparently, aggrieved Christianity (Masterpiece Cakeshop v. CCRC).

The upshot is that though he usually voted with whichever conservative bloc was ascendant, on rare occasions Kennedy would peer into the abyss and recoil. His most famous apostasy was striking down laws that manifest overt discrimination against homosexuals (Romer v. Evans and Lawrence v. Texas); he wrote the opinions legalizing gay marriage nationwide (US v. Windsor and Obergefell v. Hodges), seeming to swell with pride (sorry) at his discovery that homosexuals are people. Similarly, though he was pro-death penalty, he balked at allowing it to be used on minors (Roper v. Simmons), those with intellectual disabilities (Atkins v. Virginia), or for crimes other than murder (Kennedy v. Louisiana). In Planned Parenthood v. Casey, he stunned his supporters when he declined to overturn Roe v. Wade. He also held that the Guantanamo prisoners were eligible for habeas corpus (Boumediene v. Bush).

It is from these few cases that he found himself crosswise with his ideological allies in the culture wars—which seems a bit ungrateful, considering all he gave them. Despite his reputation among conservatives as a squish, a crypto-liberal seeking the approval of the Georgetown swells, Kennedy was the deciding vote to invent modern Second Amendment jurisprudence out of whole cloth (Heller v. District of Columbia), to shred restrictions on campaign finance (Citizens United v. FEC, American Tradition Partnership v. Bullock), to strike down Section 5 of the Voting Rights Act (Shelby County v. Holder), to expand the Takings Clause to stymie environmental protection legislation (Palazzolo v. Rhode Island), and, most recently, to undermine collective worker action by destroying public sector unions (Janus v. AFSCME) and effectively ending class arbitration of employment law violations (Epic Systems v. Lewis).

Even his famously “liberal” opinions weakened as he got older. A non-sectarian prayer at a graduation violated the Establishment Clause in 1992 (Lee v. Weisman) but a Christian prayer to open municipal meetings was fine in 2014 (Town of Greece v. Galloway). He voted to preserve Roe in Planned Parenthood v. Casey but spent the rest of his career approving one state restriction on abortion after another—including most of the Pennsylvania restrictions he reviewed in Casey. Until Sandra Day O’Connor retired, he spent a few years in dissent disagreeing with her about what their joint opinion in Casey meant. His ruling granting habeas rights to Guantanamo prisoners in Boumediene was promptly undermined by the DC Circuit, which tacked on a rule giving the government the benefit of the doubt on all evidentiary questions about a detainee’s terrorist designation and has overruled every lower court release since 2010; the Supreme Court has declined to grant certiorari to review the Circuit’s rule. He suggested that political gerrymandering had a constitutional limit (Vieth v. Jubelirer) but when the time came to actually explore that limit he punted (Gill v. Whitford, Abbott v. Perez), hiding behind jurisdictional reasons to dodge grappling with the grotesquely discriminatory facts.

Then there was his prose. His swing position meant that handing him the pen to write decisions was the price the other justices had to pay, and that pen was often purple. Whether writing about people exploring the “mysteries of life” in Casey to his florid descriptions of the bond of marriage in Obergefell to his condescending description of a hypothetical woman who may someday regret a medical abortion in Gonzales v. Carhart, sections of his opinions often read like stream-of-consciousness musings disconnected from the law he was considering.

In the end, though, any question of his political loyalties are answered by two decisions, one judicial and one personal. In 2000, he was the fifth vote to stop the recount in Florida and install George W. Bush as president. Eighteen years later he asked a new president to pinky swear that he wouldn’t act racistly (Trump v. Hawaii) while solemnly agreeing that it would be legal if he did as long as he didn’t write it down, just before he retired and allowed Trump to choose for his replacement on the Court someone unlikely to care at all.

The New York Times has reported that the Trump administration waged a “quiet campaign” to persuade Kennedy to retire, and noted that Kennedy’s son worked with Trump when he was at Deutschebank, becoming one of the Trump Organization’s primary lenders. But it hardly seems necessary to think conspiratorially. Kennedy came to the federal bench on the recommendation of California Governor Ronald Reagan, and was elevated to the Supreme Court by President Reagan. He didn’t need anyone to tell him when to retire. He knew when he’d retire all along. Kennedy was at the center of the Supreme Court, but he was never neutral.

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Charles Star is a Brooklyn-based lawyer and the host of Mic Dicta, America's best-named legal podcast. Follow him on Twitter.