I know two things about Michael Rubin. The first is that he is the billionaire CEO of Fanatics, a company that was in the news earlier this year for outfitting Major League Baseball players with pants you can see their junk through. The second is that he throws an annual “white party” in the Hamptons—one hopes his guests are able to find more opaque attire options than the ones his company offers—and that this bash has quickly established itself as the premier destination for postpandemic disgusting celebrity excess come July Fourth. Naturally, I’ve come to look forward to it each summer.
This year’s outing did not disappoint. In the video footage of the event Rubin posted on Instagram in a manner I would call gaudy if I didn’t also have to admit how much I enjoyed watching it, the party’s ability to draw A-list guests is on full display, with attendees including Tom Brady, Drake, Kim Kardashian, Megan Thee Stallion, and more. What really captured my attention, though, was a news item that trickled out a few days after the event: Photos of actor Tobey Maguire with a model named Lily Chee have sparked rumors that the two are dating.
An actor being romantically involved with a model isn’t newsworthy on its own—rich, good-looking people fraternize, news at 11!—but the possible couple is attracting notice because observers have zeroed in on Maguire’s and Chee’s ages: She is 20, and Maguire, unfortunately for those of us who are in denial about how long ago his Spider-Man movies came out, is 49. Now, there’s very little, maybe nothing, to say about age-gap relationships that hasn’t already been said, and being generally wary of them doesn’t mean we need to single out and chastise everyone who chooses to participate in one. Be that as it may, I have to say I was a little shocked by this match, if it is indeed a match. Twenty? I’m used to seeing male celebrities in their 30s and 40s date 25-year-olds and 23-year-olds, but it had started to feel like most of them at least wait for women to reach an age at which it’s legal to drink and normal to live on your own as opposed to in a dorm. Wishful thinking, I guess.
Neither party has said anything publicly to confirm this potential relationship, although Maguire’s ex-wife, Jennifer Meyer, did seemingly weigh in on social media to defend her former husband. In screenshots of a now-deleted comment, Meyer appears to have written that Maguire was merely helping a friend to her car and that he and Chee are not involved. Based on the placement of his hand on Chee’s lower back in the photo, it’s not a particularly convincing explanation, but it’s also unfair that Meyer should be confronted with such accusations in the first place. To the person who commented on Meyer’s Instagram to ask her, “Why is your ex husband banging someone 3 years older than your daughter,” you are why the age-gap conversation has become so tiresome.
But back to the Tobey Maguire of it all. Our friendly neighborhood Spider-Man? Say it ain’t so. Maguire continues to benefit from having played squeaky-clean characters in his acting career despite years of evidence of less-than-squeaky-clean associations. Chief among them might be his friendship with Leonardo DiCaprio, which is second only to Damon-Affleck in the public imagination of Hollywood bro-dom. DiCaprio’s reputation for dating younger women has been much discussed over the past few years, and he’s been notorious for his caddish behavior since the ’90s, when a magazine journalist dubbed his group of friends the “Pussy Posse.” Members of the posse allegedly included Kevin Connolly (E from Entourage), magician David Blaine, and the actor Ethan Suplee, who I recently saw is a grandfather now—and, of course, Maguire. The article, by Nancy Jo Sales, captured them carousing around the New York nightlife scene, chasing women, pulling pranks, getting into fights, and whatnot. But although Maguire was a documented member of the group, it never quite followed him around the way it did his more famous friend.
Maguire married Meyer in 2007 and remained married until 2016. Around then, there were reports that the Pussy Posse reunited and started calling itself the “Wolf Pack,” and this time there were direct references to Maguire himself hitting on much younger models, like a then-18-year-old Sofia Richie. In addition, for years, there have been rumors of his entitled behavior in the poker world. And yet, because he acted in Seabiscuit I still have trouble reconciling that he might be anything less than a sweetie pie.
I haven’t studied psychology, but I have watched the reality TV show Vanderpump Rules very attentively, and it taught me something that may be relevant here. On that show, there used to be a character named Jax whose behavior was so abhorrent—he lies with abandon, he cheats on his partners regularly, he even memorably once shoplifts on camera—that it served to mask just how bad all the other men on the show also were. They too could be downright odious (this is eventually how we got Scandoval), but because they never stole a pair of sunglasses on air, Jax served as a distraction—a sacrificial jackass if you will. Is it possible that Leonardo DiCaprio has been serving as Tobey Maguire’s sacrificial jackass this whole time, with Leo distracting the world from how terrible Tobey is by generating a steady stream of headlines about how he does things like wear headphones and vape during sex? Do we all owe Leo an apology? Have we created a monster who is poised to be even worse than Leo? Because the truly nefarious part, whether Maguire is with Chee or it’s all rumors, is that Maguire looks really good in the photos from the white party. He’s aged well, better than Leo. Leo’s been king of the Pussy Posse for a long time, but now I’m wondering who’s really been running the show.