Actually, the baker in SCOTUS's Masterpiece Cakeshop ruling lost

To be sure, in vintage Kennedy “compromisesque” style, he did make ambiguous assertions that both sides will latch onto in future cases where the merits of a merchant’s free speech or religion objections to serving same-sex couples are definitively evaluated.

Indeed, he went out of his way to emphasize that a member of the clergy could not be required to officiate at a same-sex wedding, quizzically calling this a well understood “exception” to the more general rule barring same-sex discrimination in the marketplace. But Kennedy also made similar nods to the constitutionality of traditional marriage laws in cases leading up to his Obergefell opinion striking them down.

The pattern seems clear. In his role as conservative-liberal fence straddler, Kennedy likes to proceed cautiously at first while sending out signals to lower courts as to how future cases should be decided. And once those courts have dutifully complied, Kennedy then feels comfortable in administering the coup de grace based in part on the weight of that lower court consensus.