WASHINGTON—After the arguments in Masterpiece Cakeshop v. Colorado Civil Rights Commission, the sidewalk in front of the Supreme Court on Tuesday was teeming with interested parties from both sides of the case. On one side of the court steps stood Christian cake baker Jack Phillips and Christian florist Barronelle Stutzman, whose business Arlene’s Flowers has a case pending at the Supreme Court similar to Phillips’ case. On the other side of the steps stood Charlie Craig and David Mullins, the gay couple that brought the lawsuit against Phillips’ Masterpiece Cakeshop in 2012, for his refusal to create a custom wedding cake for them based on his Christian beliefs about marriage.

Craig and Mullins talked about the “pain and humiliation” of being denied a cake, while Phillips talked about the weight of the five-year court battle on his family. Since he lost in Colorado state courts, he has had to stop selling custom wedding cakes altogether, which had made up 40 percent of his income.

"It’s been very hard on me and my family,” Phillips said. “We are struggling just to make ends meet.”

Stutzman added, “They make you choose between your faith and your life.”

That’s precisely the conflict the Supreme Court justices were trying to resolve on Tuesday: Would providing an accommodation to religious bakers like Phillips undermine civil rights laws? Was it compelled speech to require him to put out a cake that conveys a certain message? Is a wedding cake a form of speech, and what counts as speech? Is a wedding hair stylist using expression in hairdos?

“We have a very complex cake,” said Justice Anthony Kennedy, pausing to correct himself. “Case. Case and cake.”

Due to the complexity of the case and the lively debate between the justices, Chief Justice John Roberts repeatedly extended extra time to lawyers in the case—a rare move. Once again all eyes turned to Kennedy, who is the court’s gay rights champion but who seemed much more sympathetic to Phillips’ situation than anticipated. Early in the arguments Kennedy was concerned about cake shops having a sign in a window, for example, that said they didn’t do cakes for gay weddings. He also wondered, if the justices ruled in Phillips’ favor, whether bakers “all over the country” would be pressured not to sell cakes for gay weddings.

But then a key quote came in the middle of the hearing, when Kennedy stated (instead of asking a question) to Colorado Solicitor General Frederick Yarger: “Tolerance is essential in a free society, and tolerance is most meaningful when it’s mutual. It seems to me the state in its position here has been neither tolerant nor respectful of Mr. Phillips’ beliefs.” It sounded as if he was trying out a line for an opinion.

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

Kennedy was also critical of one commissioner’s remarks about Phillips’ religious freedom claims as “despicable,” hinting that that might count as viewpoint discrimination. “Suppose we thought at least one member of the commission based its decision on the grounds of hostility to religion, could your judgment then stand?”

Justice Neil Gorsuch brought up a concern about the Colorado order to Phillips, requiring that he retrain employees in light of the lawsuit from the gay couple. “Why isn’t that compelled speech?” he asked. Kennedy latched onto that too: “The state law in this case supersedes our religious beliefs, and he has to speak that to his family.”

All the justices had a dozen hypotheticals to throw at the lawyers, illustrating how difficult the line is to draw here—if it isn’t government-compelled expression for a baker to bake a custom cake, is it compelled expression if he delivers the cake to the ceremony, or if he has to cut the cake?

Alliance Defending Freedom’s Kristen Waggoner, arguing her first Supreme Court case, had clearly prepared for an array of hypotheticals. A premade cake is not speech (“it’s already been placed in a stream of commerce”), so Christian cake bakers should sell any generic wedding cakes off the shelves to gay couples. A hairdo is not speech. Other forms of participation in a wedding ceremony, like delivering a cake in the event, would fall under a free exercise claim.

“The jeweler?” Kagan asked. “Where do you put the tailor?”

“We want some kind of distinction that will not undermine every civil rights law,” said Justice Stephen Breyer.

Waggoner’s test was whether the objection is to a message (as she argues was the case with Phillips) or the person. “That’s usually very obvious,” she said.

“Well actually, counsel, that seems to be a point of contention,” said Gorsuch dryly.

American Civil Liberties Union lawyer David Cole, representing the gay couple, argued that the cake sale was about the person, not the message—that Phillips only refused because of the couple’s sexual orientation, and therefore, identity. But Kennedy was skeptical and said a baker could sell to gay people as Phillips has done, but not do gay weddings. “Your identity thing is too facile,” he said.

Likely slyly addressing Kennedy who wrote the gay marriage decision, Roberts noted that Obergefell v. Hodges “went out of its way to talk about the decent and honorable people who may have opposing views,” and that therefore it was unfair to compare them to racists. With Kennedy’s vote, the conservative justices might have a majority in this case. They could come to a very creative and narrow majority many different ways.

Outside, the divide remained fierce. A DJ with the American Civil Liberties Union blasted tunes over those who were speaking on Phillips’ side. A man struggled into a homemade costume of a cardboard Bible. Megaphone chants of “equal justice under law” drowned out the comments from Phillips and Stutzman, but quietly their lawyers felt some optimism.