When I hop on a call with Leah McSweeney to discuss her new book, I immediately have to ask about a hilarious TikTok that made the rounds on Twitter about a month ago. Staring directly into the camera in the clip, the 39-year-old fashion designer informs us that she’s invited her family to join her on a trip to Jamaica—but with a surprise twist. “They think they’re here for vacation,” she relays in her usual deadpan delivery. “They’re actually here because I’m going to confront them about generational trauma and why I have anxiety and depression issues and how it all stems from family relationships.”
She ends the video with a smile.
“I was totally joking,” McSweeney confesses. “Even my best friends didn’t know. They were like, ‘You could be joking, but you could also be totally serious about this because it’s something you would do. So we’re not sure.’ I’m like, I’m not sure either at this point.”
It says a lot about McSweeney that folks on social media (including me) and the people closest to her didn’t automatically receive her words in jest. On Bravo’s Real Housewives of New York, where she became a cast member in 2020, she presents herself as someone who’s always willing to “go there,” speaking openly about her tumultuous relationship with drugs and alcohol, her complicated dynamic with her mother, sex, religion—she just converted to Judaism—politics and everything else you’re not supposed to discuss at a formal dinner, where Bravo reality shows are set 80 percent of the time.
Likewise, it makes sense that McSweeney released a memoir titled Chaos Theory, exposing the lowest, darkest moments of her life and trying to make sense of the dream life she managed to build for herself—running a successful women’s fashion line, raising a daughter, and starring in reality television.
On the internet, the word “chaos” is severely overused, describing anything and everything from an actual war to a celebrity’s terrible outfit. But from the moment you crack open Chaos Theory, McSweeney’s application of the term to describe her adolescence and young adulthood seems apt—so much so that she looked to the mathematical and scientific study of chaos to understand it all.
Chaos Theory begins with McSweeney recalling her days as a rebellious kid attending a bougie all-girls Catholic school in Manhattan on financial aid, with classmates like Nicky Hilton and a little singer known then as Stefani Germanotta. (Think Lady Bird but on the Upper East Side). In the eighth grade, she was deemed a “bad influence” on her affluent peers by the school’s headmistress and told to leave. She credits this frustrating moment with setting a wild chain of events into motion.
Rather than take her expulsion as a cue to become a better pupil, McSweeney, feeling outcast, leaned into her defiant tendencies even more. She became especially resentful when her family abruptly moved to suburban Connecticut after she completed middle school, adopting a precarious lifestyle that included traveling back to downtown New York to go to raves with her friends and consume a bunch of drugs.
In Chaos Theory, she writes vividly about her first time trying meth, going on days-long benders in the city, altercations she would have at home with her parents and subsequent stints in rehab. With all these experiences, the author knew she was destined for a tell-all eventually but was surprised by how triggering the writing process was.
“I thought I had reckoned with it until I started writing about it,” McSweeney tells me. “While I’m writing this book, I’m thinking, ‘How the hell could I have ever acted like that or had such disregard for my life and my parents’ life and everyone around me?’ It’s really kind of mind-blowing.”
McSweeney’s dependence on drugs and alcohol would follow her into her twenties and even after she gave birth to her now-14-year-old daughter Kier. She also writes about being diagnosed with bipolar II disorder around her 30th birthday— something that was brought up by castmate Ramona Singer on RHONY during her first season—and being prescribed an overwhelming dose of drugs.
In between these rather serious revelations, the author manages to paint a fascinating portrait of late ’90s-early 2000s rave culture and nightlife in downtown New York—a sound and aesthetic that musicians, zoomers on TikTok, and fast-fashion brands have been trying to emulate recently. She tells me the nihilism of her generation post-9/11 contributed to the way they partied.
“It shook us as a generation, especially us living in the city,” McSweeney says. “The way we partied and shit, we were like, ‘The fucking towers are gone. We’re going to go nuts now.’ Maybe this generation has some kind of trauma, like the pandemic, and they’re somehow making a correlation.”
In addition to therapy and proper medical care, McSweeney would eventually find the stability she needed as a young adult in the exploding downtown streetwear scene, starting Married to the Mob in 2004 with the help of her then-boyfriend and father of her child Rob Cristofaro, who founded the popular streetwear brand Alife. She was also able to fund the company after winning a lawsuit against the NYPD after a shockingly (but not so shockingly) violent incident that left her with fractured teeth—a story she’s told publicly and describes again in her book. Since then, she’s become a certified downtown “it” girl and formidable industry name, receiving co-signs from Rihanna, deals with Nike and even a $10 million trademark infringement lawsuit from Supreme founder James Jebbia that was eventually dropped.
Still, with all her professional accomplishments and girl-bossery, McSweeney describes her recent placement on Real Housewives of New York as “the most feminist endeavor she’s ever partaken in.”
“Real Housewives gives women a chance at fame, stardom and to be a part of a pop-culture phenomenon at an age where we’re told we have no value anymore,” McSweeney says passionately. “We’re much more valued on our personalities than our looks.”
She continues, “Of course, there’s having nice clothes and all that. But no one is loving someone on the show because of their beauty, right? It’s about what they bring to the show. And I think that’s fucking dope because there’s not a lot of spaces in Hollywood and in the entertainment industry where that exists.”
While McSweeney made a big splash during her first year on RHONY as an exciting alternative to the show’s older, more conservative cast, her sophomore season was a lot rockier. For one thing, McSweeney’s grandmother was dying during filming, and she spent the first handful of episodes grieving and lashing out toward some of the cast. The season was also widely criticized online by fans in response to conversations about race, which were primarily being led by the show’s first Black housewife, Eboni K. Williams, who was hired that year. McSweeney, Williams’ designated friend on the show, was also willing to discuss race and politics with the other women.
“It was pretty horrible,” McSweeney says. “I think if it was fair and warranted then it would’ve been better, but it was just so unfair. We only had five women. Eboni was not in an easy position. The other women were not in an easy position. I was dealing with my grandmother’s death.”
Viewers reacted negatively to Williams’ “introduction” of social issues onto the show, while others called for Ramona Singer to be fired for her displayed ignorance. The intense response to McSweeney was particularly surprising, given her fan-favorite status just a year ago. Producer Andy Cohen even remarked that he had never seen Housewives fans turn on a cast member that quickly.
“Mentally, emotionally, I was not all there,” McSweeney admits about season 13. “And I was not enjoying myself. People are used to RHONY being RHONY. And people were just vicious about it.”
Leah McSweeney on Watch What Happens Live with Andy Cohen
Bravo“The other women are so used to it,” she goes on. “They’ve been doing this for so long that they’ve turned a part of themselves off. And they’re not affected by it. But I’m very new. I’m not going to speak for Eboni, but she was brand-new. We don’t know how to turn that part off. Maybe I don’t want to turn it off either. So it was hard, but once Rihanna posted that she was Team Leah, I was like, ‘OK bitches, now what?’”
In addition to some viewers finding McSweeney’s emotional rawness off-putting last season, she also faced scrutiny after telling her castmates that she wasn’t particularly enthusiastic about picking between Joe Biden and Donald Trump during 2020’s presidential election in an episode. Social media users labeled her comments irresponsible and brought up the admission on Danny Pellegrino’s “Everything Iconic” podcast that she didn’t vote in 2016.
“That’s the other thing I couldn’t understand,” McSweeney says about the backlash. “Here I am being honest about something a lot of people feel—that I don’t want to choose between two very old men to run the country.”
“That part I don’t care about because that’s my real view,” she asserts. “You can criticize me all you want about that. That’s the way I feel. Also, I’m entitled to feel the way I feel. So I’m actually very happy I was honest about that.”
While some aggrieved RHONY fans on Twitter may be petitioning for her to get off the show, they could very well see her on the recently announced reboot of the series that will coincide with a spin-off for the show’s older cast members. While no casting decisions have been announced—and McSweeney is mum on her potential involvement—she seems to at least be in Bravo’s good graces, as she appeared on Watch What Happens Live last week and answered questions about whether her friend Julia Fox should join the new show.
Whatever the outcome, McSweeney has always had a take-me-or-leave-me attitude, something that’s fully present throughout Chaos Theory. And the entrepreneur seems eager to continue telling her own story without anyone else’s say-so.
“I was just saying yesterday,” she says. “I maybe need to write book No. 2. And it takes place between 1995 and 2000, which I basically think would just be Euphoria.”
