I know two things about Michael Rubin. The first is that he’s the billionaire CEO of Fanatics, a company that made headlines earlier this year for outfitting Major League Baseball players with pants that show their private parts. The second is that he throws an annual “white party” in the Hamptons—hopefully, his guests can find more opaque clothing options than his company offers—and that the party has quickly become known as a Pride party. THE prime destination for post-pandemic celebrity gross-out excess on the 4th of July. Naturally, I look forward to this moment every summer.
This year, the party did not disappoint. In the event video that Rubin posted to Instagram in a way that I would call flashy if I didn’t also have to admit how much I enjoyed watching it, the party’s ability to attract A-list guests is on full display, with attendees including Tom Brady, Drake, Kim Kardashian, Megan Thee Stallion, and more. What really caught my attention, however, was a piece of news that leaked a few days after the event: photos of actor Tobey Maguire with a model named Lily Chee sparked rumors that the two were dating.
An actor having a romance with a model isn’t news in and of itself—rich and beautiful people fraternizing is news at age 11!—but the potential pairing is drawing attention because observers have focused on Maguire and Chee’s ages: She’s 20, and Maguire, unfortunately for those of us in denial about how long it’s been since she and Chee hooked up, has been very close to her husband. Spider Man There is very little, if anything, to say about age-diverse relationships that hasn’t been said before, and being wary of them doesn’t mean we should isolate and berate everyone who chooses to participate in them. Regardless, I have to say I was a little shocked by this match, if it is a match. Twenty? I’m used to seeing 30- and 40-year-old male celebrities dating 25- and 23-year-olds, but I’ve started to get the impression that most of them are at least waiting for women to reach an age where it’s legal to drink and normal to live alone rather than in a dorm. Wishful thinking, I guess.
Neither party has said anything publicly to confirm this potential relationship, though Maguire’s ex-wife Jennifer Meyer has seemingly come to her former husband’s defense on social media. In screenshots of a now-deleted comment, Meyer appears to have written that Maguire was simply helping a friend into her car and that he and Chee were not involved. Based on the position 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 is facing such accusations in the first place. To the person who commented on Meyer’s Instagram asking, “Why is your ex-husband sleeping with someone 3 years older than your daughter,” you are the reason the age gap conversation has become so boring.
But back to Tobey Maguire. Our friendly neighborhood Spider-Man? Say it ain’t true. Maguire continues to benefit from playing impeccable characters in his acting career despite years of evidence of less-than-impeccable associations. Chief among them might be his friendship with Leonardo DiCaprio, who is the second-biggest actor in the popular Hollywood imagination after Damon Affleck. DiCaprio’s reputation for dating younger women has been much discussed in recent years, and he’s been known for his thuggish behavior since the ’90s, when a magazine reporter dubbed his group of friends the “Pussy Posse.” Members of that group reportedly included Kevin Connolly (E of Entourage), magician David Blaine and actor Ethan Suplee, whom I recently saw as a grandfather – and, of course, Maguire. The article, written by Nancy Jo Sales, shows them partying in New York nightlife bars, chasing women, playing pranks, fighting and more. But while Maguire is a well-known member of the group, he never followed him around like he did his more famous friend.
Maguire married Meyer in 2007 and remained married until 2016. Around this time, there were rumors that the Pussy Posse had reunited and started calling themselves the “Wolf Pack,” and this time, there were direct references to Maguire himself hitting on much younger models, like Sofia Richie, then 18. Additionally, for years, rumors swirled about his pretentious behavior in the poker world. And yet, because he played in Sea biscuit I still have a hard time accepting that he could be anything other than a little cabbage.
I didn’t study psychology, but I watched the reality TV show Vanderpump Rules I watched the show very carefully, and it taught me something that might be relevant here. On that show, there was a character named Jax whose behavior was so odious—he lied freely, he cheated on his partners regularly, he even committed a memorable shoplifting on camera—that he served as a way to mask how evil all the other men on the show were. They too could be downright odious (which is how we eventually got Scandoval), but since they never stole a pair of sunglasses on air, Jax served as a distraction—a sacrificial idiot, if you will. Is it possible that Leonardo DiCaprio served as Tobey Maguire’s sacrificial idiot this whole time, with Leo distracting the world from Tobey’s horror by generating a constant 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 that is about to be even worse than Leo? Because the worst part, whether Maguire is with Chee or if these are just rumors, is that Maguire looks really good in the white party photos. He has aged well, better than Leo. Leo has been the king of the Pussy Posse for a long time, but now I wonder who is really running the group. to show.