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It’s a position that Justice Anthony Kennedy has found himself in many times before. The Supreme Court justice is likely to be the deciding vote in Masterpiece Cakeshop v. Colorado Civil Rights Commission, a case heard before the nation’s highest bench on Monday.

Judges heard oral arguments in the pivotal case, in which Colorado baker Jack Phillips claims that he shouldn’t be forced to bake cakes for same-sex weddings. In 2012, Phillips denied services to Charlie Craig and David Mullins, a gay couple planning their nuptials. The Colorado Civil Rights Commission later ruled that the refusal violated the state’s nondiscrimination laws, which prevent unlawful bias on the basis of sexual orientation.

The nine justices’ sympathies appeared to fall along party lines. The moderate Kennedy found himself wedged somewhere in the middle.

The court’s four-member liberal bloc—which includes Elena Kagan, Sandra Sotomayor, and Ruth Bader Ginsburg—questioned Phillips’ lawyers as to their assertion that baking a cake constitutes artistic expression and, thus, should be protected under his First Amendment rights. Kristen Waggoner, an attorney with Alliance Defending Freedom, compared a wedding cake to “creating a painting.”

Justice Ruth Bader Ginsburg asked where the line is drawn on artistic expression.

“Who else is an artist?” asked the 84-year-old justice, the court’s most reliably left-leaning member. “Say the person who does floral arranging, owns a floral shop? … How about the person who designs the invitation?”

Kagan jumped in to continue the line of questioning.

“So the jeweler?” she added. “Hair stylist? Why is there no speech in creating a wonderful hairdo? The makeup artist? It’s called an artist. Why wouldn’t that also count?”

“When have we ever given protection to a food?” Justice Sotomayor wondered.

But the other side of the bench appeared moved by Phillips’ claims that Colorado’s civil rights commission discriminated against his religious beliefs by mandating he undergo sensitivity training. Trump appointee Neil Gorsuch claimed that the decision was “possibly in violation of his free-exercise rights.”

Kennedy added that such treatment would force Phillips to tell his family “that state law... supersedes our religious beliefs.”

The Reagan appointee is a conservative moderate often called upon to be the tie-breaker when the two sides cannot reach a consensus. That has given Kennedy a great deal of power: The judge has been behind some of the Court’s most progressive decisions on LGBTQ rights. He wrote the majority decisions in both Lawrence v. Texas, which struck down state prohibitions on sodomy, and Obergefell v. Hodges, which gave same-sex couples the right to wed.

Kennedy worried that siding in favor of the Colorado bakery would serve to undermine the court’s 2015 marriage equality ruling. “It means that there’s basically an ability to boycott gay marriages,” he said.

The right-leaning judge added that allowing people of faith to discriminate on the basis of their sincerely held religious beliefs could be a slippery slope to Jim Crow-era discrimination. Kennedy claimed that Christian bakers could place signs in their window stating, “We do not bake cakes for gay weddings.”

“And you would not think that an affront to the gay community?” he asked Noel Francisco, the Principal Deputy Solicitor General who appeared on behalf of the Trump administration. The White House has backed Phillips in the case.

But Kennedy’s written opinion in the Obergefell decision signaled he may be sensitive to the arguments put forward by religious claimants on Monday.

“[I]t must be emphasized that religions, and those who adhere to religious doctrines, may continue to advocate with utmost, sincere conviction that, by divine precepts, same-sex marriage should not be condoned,” the 81-year-old argued at the time. “The First Amendment ensures that religious organizations and persons are given proper protection. ... The same is true of those who oppose same-sex marriage for other reasons.”

Kennedy’s line of questioning in the 80-minute oral argument, which ran well over the scheduled hour of debate, will likely keep LGBTQ advocates awake at night as they attempt to determine where his vote will fall.

The justice questioned whether Mullins, Craig, and the Colorado Civil Rights Commission had been sufficiently “tolerant or respectful” of Phillips’ faith beliefs, stating that “other good bakery shops... were available” to accommodate their requests. He claimed, in particular, that the commission’s verdict indicated a “hostility to religion.”

“Tolerance is essential in a free society,” Kennedy said. “Tolerance is most meaningful when it’s mutual.”

He took particular issue with a statement from Commissioner Diann Rice in which she claimed that religion has been used to “justify all kinds of discrimination throughout history,” pointing to the Holocaust and slavery. “[T]o me, it is one of the most despicable pieces of rhetoric that people can use... their religion to hurt others,” she claimed during debate over the original complaint five years ago.

That quote has been taken out of context and exploited by the ADF to prove bias against people of faith, reports The Nation’s Sarah Posner. The firm is behind the introduction of numerous anti-LGBTQ bills across state legislatures, including legislation denying transgender people restroom access corresponding with their gender identity.

Posner said religious conservatives have falsely claimed that the Colorado civil rights board compared Phillips to a Nazi.

“[T]he statement does not evince a hostility to religion itself, only opposition to the invocation of religion to justify discrimination,” she wrote. “Nonetheless, Kennedy and others seized on it to suggest that fears of anti-Christian bias might indeed be real.”

In perhaps the most damning strike against LGBTQ rights, Kennedy appeared unconvinced that the Christian baker’s actions were motivated by animus toward same-sex couples. He told David Cole, an ACLU attorney representing Craig and Mullins, that an identity-based explanation for Phillips’ actions is “too facile.”

“It’s not their identity,” he said. “It’s what they’re doing.”

Analysts appeared divided as to whether Kennedy’s often conflicting remarks indicated he would cast his vote in favor of the Christian baker or the rights of LGBTQ people, as the justice has in the past. National Review correspondent David French claimed the judge “put identity politics on blast” in a tweet, while Vox’s German Lopez argued he was “sending mixed signals.”

Both sides will have to wait until June to find out where Kennedy stands, when the Supreme Court is expected to issue its formal ruling.

Photo by Eric Thayer/Getty Images

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