Conservatives are lining up behind Caitlyn Jenner. Jenna Ellis, former senior counsel to Donald Trump, says that Jenner’s campaign for the governorship of California shows “how non-inclusive and intolerant the leftists really are.” Paul Gosar, the firebrand Arizona congressman, approvingly notes that the “left is triggered” by the candidate. John Fund, the national affairs reporter for National Review, tweets: “Caitlyn Jenner’s new video for CA governor is SUPERB. As a Californian, I actually cried.”

It should not be surprising that conservatives have come to regard Caitlyn as stunning and brave. Despite its residual reputation as the party of family values and Yankee modesty, the GOP has long relied on celebrities who deviate from established standards of taste and propriety. Donald Trump, with his gold-plated aesthetics and “locker-room talk,” is only the most recent example.

When Arnold Schwarzenegger ran his populist campaign to become governor of California, an old interview surfaced in which he bragged about drug use and group sex. He shrugged it off and so did voters. He was accelerating the trend begun by Ronald Reagan, a Hollywood star turned governor of California and the first divorcé to win the presidency.

In this sense, Jenner’s candidacy is less novel than it may seem. Jenner wears makeup. Reagan did too, at least professionally. Jenner has reshaped his body and taken hormones. So did Arnold. Keeping up with the Kardashians is vulgar. So is Conan the Barbarian, and so is the governor’s mansion Reagan built, as Joan Didion memorably observed.

Behind these superficial resemblances stands a basic fact. Conservatives have been banished from elite institutions. Their views are treated as deviant by polite society. So they must look elsewhere for leaders. Because of their name recognition and ability to generate free press, celebrities can reach a wide public without the support of the power elite. They will tend to understand, even share, popular tastes. But they are also more likely to live the kinds of lives you read about in tabloids than the kind documented in the class notes of Harvard Magazine.

One need not be overly concerned with respectability to regret this dynamic. Divorce, which Reagan did much to normalize, has produced untold agony. There is no reason to be more optimistic about Caitlyn Jenner’s campaign to normalize transgenderism.

For that is just what he has embarked upon. In his 2017 autobiography, Jenner writes, “What I am trying to do, what I am doing, is to ultimately make the mainstream public comfortable with us [transgender people].” He believes that he is uniquely situated to change opinion on the right: “I believe that we desperately need conservatives like myself who have a platform and can use it to enlighten fellow conservatives, reminding them of the Golden Rule—that trans people should not be judged on moral or religious grounds but rather treated as fellow human beings.” Jenner is not just trying to win the governorship. He is trying to change American attitudes.

Yet his own attitudes are more complicated than might be expected from an avatar of the transgender movement. Under the new orthodoxy, anyone who uses the wrong name or pronoun risks being cast out of respectable society. Jenner takes a more tolerant view. He wants the transgendered to be accepted on their own terms, but he seems uncomfortable when that aspiration leads to the policing of speech. After Joy Behar was denounced for referring to Jenner as “he” on The View, Jenner told her not to worry: “I’m not about cancel culture. I know where your heart is. California has bigger issues than pronouns.”

Jenner himself has run afoul of the new orthodoxy. After his transition in 2015, he gave an interview in which he expressed only the most reluctant support for gay marriage. “I’m a traditionalist,” he said. “I kinda like tradition and it’s always been a man and a woman … [but] if that word—‘marriage’—is really, really that important to you, I can go with it.” Outrage was widespread. More recently he shocked progressives by saying that biological boys should not be allowed to compete in girls’ sports.

Jenner has been surprised to find how utterly members of the transgender movement reject his live-and-let-live philosophy. “For a community pushing for acceptance,” he writes in his autobiography, “we can sadly be brutally judgmental of each other. We insist upon tolerance, but only to an extent. We want inclusion, but aren’t as inclusive at times.”

Despite this tension, Jenner shares the basic convictions of transgender activists. Jenner visited the parents of one transgender teen who had committed suicide and reflected on his death. “It wasn’t just depression and repeated cyberbullying that made life such hell for him,” he writes. “It was also adults who refused to accept Kyler or address Kyler by the correct pronoun.” When a transgender woman wrote to Jenner saying that a bill in South Dakota limiting transgender bathroom use was harming her, Jenner concluded that “she was right to think the atmosphere was toxic.”

In Jenner’s view, the transgender movement is guilty of inconsistency. But it is hard to see how his own beliefs about transgenderism are compatible with the freedom he seems to prize. If misgendering is the cause of transgender suicide, we need restrictions on speech. If socially conservative bills harm people who would otherwise be healthy, then social conservatism must be stamped out. Jenner’s easygoing instincts are winsome, but they cannot be reconciled with what he has come to believe about his identity.

He is not the only one who suffers from this confusion. A number of well-intentioned writers have protested the illiberal effects of transgender activism while insisting that we should affirm transgender identity. They suffer from an acute form of the illusion that freedom need not be tied to some idea of the good and the true. A society that regards transgenderism as normal and healthy will inevitably sanction those who disagree. Caitlyn’s rise shows that we are confused not just about gender, but about the nature of liberty.

Matthew Schmitz is senior editor of First Things magazine, and a contributing editor at The American Conservative.