above: “Most of my film and theater work has been very female-dominated, like women writers, women directors, and I really value that,” says Maggie.
There’s a jaw-dropping scene you might recall midway through the first season of Showtime’s award-winning hit Billions (2016-2023), in which Dr. Wendy Rhoades, Axe Capital’s in-house performance coach, is called to a meeting with her boss, hedge-fund billionaire Bobby Axelrod. They discuss trust, prioritizing meaning over happiness and cutting a high-stakes deal under the threat of a criminal ass-whupping. It would be just another day at the office, except that it’s night, and Wendy and Bobby are in a private, candle-lit spa pool, naked.
Now that’s rich, even for Greenwich.
In the hands of lesser actors and storytellers, the whole thing could be written off as a ratings grab. You couldn’t pick a steamier setting, and the duo’s undeniable chemistry sparks a will-they-or-won’t-they dynamic that slow-burns throughout the series. But with Maggie Siff at the helm as Wendy, nudity takes a backseat to nuance. With each eye shift and head tilt, we wonder: how far will Wendy go to keep the peace between two warring men? To whom and to what will she be most loyal? Where does her own freedom fit in? If the ends justify the means in Billions-land, will they ultimately end Wendy?
That the series was such a chess game of male egos only heightens Wendy’s importance as an empath who could also think ten moves ahead. The key was finding the right person to bring her many layers to life. “The moment we saw Maggie read the part of Wendy, we knew she had an innate understanding of her,” says Billions co-creator and Greenwich resident David Levien. “Maggie was immediately able to communicate how Wendy saw through the men she was dealing with, not in order to belittle them, but rather to help them be better versions of themselves and to be incredibly appealing while doing it. It was our goal for Wendy to ‘win’ the first season, overcoming both Chuck and Axe and their machinations, and Maggie had the presence and formability as an actor to pull that off beautifully.”
Last month, Levien and his Billions co-creator, Brian Koppelman, were honored alongside Maggie and castmember David Costabile, who played Wags on the series, at the Greenwich International Film Festival’s Billions tribute at the Bruce Museum. Against a backdrop of Hockneys and Warhols, the event was a celebration of the series’ seven thrilling seasons as well as a hat-tip to Maggie Siff, who embodies GIFF’s commitment to outreach.
“In our tenth year as a female-founded organization spotlighting changemakers at the forefront of storytelling and social impact, we couldn’t be prouder to shine a light on Maggie, who in addition to her tremendous talent, has given of herself through dramaclub.org, which nurtures incarcerated children through improv,” says GIFF’s Chairwoman of the Board, Wendy Stapleton. “Maggie carries on our tradition of strong women in the arts who champion the underserved with creativity and compassion.”
TAKING THE PLUNGE
When I first meet Maggie, I’m struck by how much softer she looks and sounds than Wendy. Gone is the coiffed, spike-heeled, black-sheathed tamer of lions, and sitting in her place is an ethereal, wavy-haired beauty in a peasant top with subtle stripes that echo the colors of the Maine coastline. It’s early July, and Maggie’s relaxing up here at her sister’s home, a cozy pause from the clip of her daily life in Brooklyn. Cut a path through the woods out back and you’ll land at her mother’s doorstep. It’s their little family compound, seemingly a million miles north of everything.
“My life up here is, you know, family and cooking and being on the beach as much as possible … we’re beach bums,” she says, smiling at her ten-year-old ponytailed daughter, Lucy, who is felting and listening to Harry Potter on her earbuds nearby. “My goal when I’m up here is to get into a body of water every day, so we have our spots that we love to go to. Yesterday, we went to a little secret beach that we love. It’s very rocky, and the water’s freezing cold, and we like to plunge there.”
Maggie has certainly earned a vacation. She just turned fifty, wrapped a six-week run starring as a PTSD-plagued former war correspondent in the off-Broadway play Breaking the Story, and delivered the 2024 commencement address at her alma mater, The Bronx High School of Science. When I point out that all of this went down in under six days, she humbly deflects. “When they asked me to do the commencement address, I was like, ‘That’s a joke, right?’” Maggie says, lightly raising an eyebrow. “Like, what could I possibly have to offer these kids? I mean, I went to that school, and it’s an amazing place in an amazing community, but it’s a huge school. And a lot of these Bronx Science alums are not like me. They go on to win Nobel Prizes in physics and things like that.”
I tell her it’s apples and oranges, to which she nods and laughs, though she worried her words wouldn’t land on everyone. We come into being with others, she explains, so how does one come into being with 900 young people about to launch, plus their families, all with diverse backgrounds and ideas of what it means to be successful in the world? Stepping on a soapbox and declaiming herself is an uncomfortable place for her, which is why you won’t find her on social media. She’s a one-on-one kind of person, a giver-and-taker, an intimate interactor. But after talking to high school friends who insisted she should do it, Maggie stepped up to the challenge.
Drawing on her creative background, she took to the podium and shared, among other universal principles about being a transformative person, a fake-it-till-you-make-it mantra she learned as an actor that is more intuitive and far-reaching than it sounds. “It’s a little trick of the mind,” she says, “that gives yourself permission to have, like, a larger container or a larger imaginative experience of who you could be in the world.”
It was a similar shape-shifting element, a performative sleight of hand, that first captivated a young Maggie. Her family lived in the Bronx, but she remembers a trip down to North Carolina while her father, a former actor and professor of Victorian literature who returned to the stage at forty, was starring in a play called The Dining Room.
“I was about eight when I went to see it, and me and this other kid, the son of one of the actresses in the play, sat in the theater and watched it every night for a week,” Maggie recalls, noting that by week’s end, they could perform it word-for-word for their parents. But what stuck with her, mesmerized her, really, was the puzzle of one particular scene.
“This woman walked on stage and dropped her keys, and then she picked them up, and I was like, Oh, it was a mistake. She wasn’t supposed to drop her keys. And then the next night, she did it again, and I realized that it was a piece of behavior that she had chosen, or maybe it was scripted,” she says. “And this thing of performing it so that you don’t know whether it’s real or not was so fascinating to me. It felt like a magic trick, you know? Like, she could do it every night in such a way that it felt so real that you thought it was a mistake, but then it gets worked into the character.”
It wasn’t until 14 years later, after Maggie graduated from Bryn Mawr College with a degree in English in 1996, that she dove into acting. Attending an all-female school was a gift, she says in retrospect. “It definitely helped forge or define my feminism and my identity as a woman. And when I got out of college and I was doing theater in Philly, I remember just being like, Oh. I’m 22, and actors are sidling up and making little sexist comments or suggestive comments and I’m just realizing that the texture or the tenor of everyday life has so much smarminess in it for young women. I was like, Wow, I am not used to this. This is fascinating.”
MAD MOVES
It would be Maggie’s paternal grandmother, a Russian immigrant from the Lower East Side, whom she would channel in her big break as department store heiress Rachel Menken on AMC’s Mad Men in 2006. “I remember when we first got into hair and makeup when we were shooting the pilot, and I was like, Oh my God, I look like my grandmother.”
It was the same immigrant grit, Maggie says, that made up the best parts of her savvy, business-minded character. “Rachel was ahead of her time. She was trying to carve something out for herself, and nothing was going to get in the way of that. It’s part of the revelation she has the very last time you see her in that first season, where she’s like, ‘You’re a coward.’”
That coward, of course, would be Jon Hamm’s Don Draper, catnip to just about anyone with a pulse, who wanted Rachel to run away with him to California. He was only running away from himself, that was clear, but many a woman of that time would’ve packed her bags anyway. That’s why Rachel’s chutzpah in staying put was so compelling—it wasn’t your typical response to an alpha male. Then again, Rachel was the true alpha.
“She realizes that he’s not a strong person and that there was just no going forward,” Maggie says. “She would be sacrificing too much of what had already been her life’s work, so she had to cut herself free of it.”
More than a year would pass before Maggie and the mostly New York-based Mad Men cast would shoot the first season in Los Angeles in 2007. Maggie figured her move would be a six-month stint, but after the tumultuous break-up of a long-term relationship as soon as she landed out west, Maggie realized she wasn’t going back to New York. And so began her abrupt transition to the City of Angels. Thanks to a Philly friend, she found herself living in a cool Craftsman-style house in Echo Park with five male roommates.
“We referred to it as the husband farm,” Maggie says, fondly. There was a film student, a future director, a landscape architect, and a cabinet maker, she tells me, which makes me wonder about the last one: a butcher or baker, perhaps? “They were all sort of strapping and eligible, and I was like, interested in none of them. I was just friends with all of them. It was this great, communal kind of very not-glamorous LA.”
Maggie was still living on the husband farm, doing television and film work, when she landed her second major series in 2008, FX’s Sons of Anarchy, starring as Dr. Tara Knowles. “I think the reason I was drawn to Tara and Sons of Anarchy was because it was so different from Mad Men,” Maggie says. “The show was a very operatic, pulpy, violent, juicy, messy family drama mixed up in this biker club.”
Maggie remembers a moment early in the fourth season, when SOA’s showrunner downloaded her on what would happen to Tara next. He described how she would have an accident that would ruin her hand, and as a surgeon whose only way out was through her career, that would do something to her psychically that would complete her transformation, sucking her deeper into the muck of the story. Maggie was all in. “I knew that the rest of the show for however long I was on it would be interesting,” she says. “The escape hatch was closing, basically. Like, there’s no turning back.”
Another element that drew Maggie to the series was the love story beating through the criminality and tragedy of it all. Interestingly, not long after she’d started SOA, Maggie found her own true love with clinical therapist Paul Ratliff, whom she’d met through a mutual friend. The two had an immediate connection, and began a long-distance romance.
“He’d been living in London for seven years, but he was planning to move back to New York and I was living in LA, and so he kind of moved back to New York, and I was going back and forth, and then I just kind of took him with me to LA,” Maggie says of their nomadic beginning.
In case you were wondering, Paul did not join as the sixth man on the husband farm—Maggie had since moved—but he did become her husband in 2012. By then, the two were in a bicoastal groove, bouncing between LA and their home in Brooklyn Heights. Maggie did plays in New York during SOA’s off-season, and Paul’s career allowed him to be geographically nimble. “He loved to travel,” Maggie says. “He loved to up and go. Those years before we had my daughter, where we were going back and forth … we loved that.”
THE SANDBOX
Maggie and Paul’s daughter Lucy was born in 2014, and the family settled into Brooklyn full-time three years later when Lucy started school. By then, Maggie was starring in Billions as a doctor of a different kind: psychiatrist Wendy Rhoades, the voice of reason holding the series and its brilliant, tortured psyches together. But being the voice of reason, even in dominatrix boots, has its narrative limits. Maggie wanted to jump in the sandbox, get Wendy’s hands dirty, just like the boys.
Sometime between the first and second season of her Billions journey, Maggie sat down with its co-creators, who liked to check in during the hiatus about where the characters had been and where they were headed.
“I said to Brian and Dave, ‘I don’t want to be the moral center. Men get to inhabit this gray area, especially in this show, that seems like more fun from a creative point of view. I want to be able to tell this story, to be part of these stories in substantive ways, you know, carry story, propagate story, create story, be responsible for story. And if we’re doing it in this world and these are the terms, then I don’t want to sit on the sidelines being the good person or the good woman,’ and I think they were interested in that and they heard that, and I think there was an arc for her that was kind of about coming back to her moral center, which I think was interesting,” she says.
Maggie recalls other collaborative conversations they had further into the series as Wendy ebbed and flowed. “I was like, ‘Wendy needs to get her mojo back. You know? Like, where did the fun go?’ And then if she got too divorced from some moral center, I would be like, ‘and now we need a little bit of that.’ I think the character worked best when there was this alternating between states of sort of moral correction or being morally correct and the slide away and the scramble back, and the messy emotional life with these two men with whom she’s in love with in different ways and this struggle to understand her own identity.”
The timing of ’ rollout also had an impact on Wendy’s evolution. “We started doing the show before #MeToo, before Black Lives Matter, before all of these big social and civil movements kind of shook us all,” Maggie says. “And I feel like, in a way, the story of toxic masculinity was more at the fore, and also this idea of the antihero being the thing we were all really interested in. But I think that over time, the antihero became a little bit less interesting. And who I wanted to be as a woman in that world kind of shifted a bit.”
What emerged, in the end, was a more actualized, autonomous Wendy. Perhaps in this newly-defined territory, unlike that amorphous night in the spa pool, meaning and happiness could finally converge on her own terms, apart from Axe and Chuck. “It’s not like either of those relationships end, but where we leave them, they are each inhabiting their own space,” Maggie says. “But the show actually ends with her and her family, which I think is also nice, that it’s kind of like the familial relationship with Chuck and with her children.”
ENDINGS AND BEGINNINGS
Behind the scenes of Billions, however, Maggie’s own family was suffering. Paul had been diagnosed with brain cancer during the pandemic, while Maggie was on hiatus. When filming resumed, things got tougher. “I was taking care of him, and we were living up in Maine, and I was commuting down to Brooklyn for work,” she says, noting that thankfully, her scenes were consolidated so she could swoop in and shoot for a few days, then return to Paul and her family.
I ask if working during that time was at all cathartic for her, and she gently corrects me, saying it was more connective. “And I will say that it was always very hard to leave, but once I was there and working, it felt incredibly good to step into the world of this character that I loved,” she says. “It ended up feeling like a supportive and nurturing experience through this really painful time. And in that way, it fed me. I don’t know if that’s a correlation between Wendy feeding Maggie, I just know that for a couple of days a month, I could go be somebody else in a world that felt loving.
It was like a little portal. It was an escape, and it kind of eased something in me a little bit for the time that I got to do it. And Brian and Dave and our producer, April Taylor, made it so that I could do it, which was really nice. They were unbelievable to me during that process.”
Does she miss it? The show, the character, the people?
She pauses before responding. “When we shot the pilot, my daughter was nine months old, and by the time the show ended, my husband had passed, and, you know, it’s like this whole life cycle,” she says. “The last few years of it were so hard that I was also ready to move into the next phase. But you carry the people you need with you forward.”
Right now, forward movement involves a delicate life-work balance. Maggie will be doing a short film with friends soon, and other projects are percolating. She’d love to team up with more female creators and directors. And of course, she continues to support dramaclub.org, founded by her NYU classmate, Josie Whittlesey, which brings the gift of performing, and with it a tangible freedom and levity, to young people at Rikers Island and other detention facilities. “There is something about the marriage of the work of theater and improv and transformation applied to children in the most profound constriction imaginable that just moves me,” Maggie says. “It does something in my brain and my body. I can’t think of anything that feels more important.”
Maggie is very interested in doing more theater as well, but she can’t do it all the time. The lifestyle and nighttime-ness of it makes things tricky as a single parent. She has been saying no a lot these days, especially to work that would take her too far afield, and is mostly at peace with that. But if the right project comes along, she and Lucy might go have an adventure together. “It all walks a line,” she says. “If I was in a different situation, if my husband were still here, then the calculus might be a little bit different, but it’s … yeah, it’s complicated.”
Out of nowhere, I have to ask: what did Maggie do on her 50th birthday? Somehow, it feels critical to know. Did she blow out a candle?
She blinks a bit, mentally scrolling back a few weeks—had there been a candle on the day?—and seems to enjoy arriving at the answer. It was a rolling celebration, she says, which included a small surprise party with family and neighbors that Lucy had sweetly plotted. And yes, they had a little cake for her at the theater on the night of her actual birthday, and she blew out a candle. “I felt full of gratitude and joy that I got to go on stage and perform and do what I love with people that I really respected,” she says. “It was not a hard birthday, this one, for whatever reason, I just feel like it feels like a substantial number. I feel lucky to have made it this far.”
The celebration didn’t end there. After her performance, Maggie enjoyed a meal with a friend at Tavern on the Green. And then, further uptown, in the wee hours of the morning, Maggie found herself sitting in a pew in the Cathedral of St. John the Divine. “They have a summer solstice concert every year that starts at, like, four in the morning,” she says, describing a saxophone, a trumpet, a piano, an organ, maybe a string. “Anyway, they play in the dark,” she continues, gently lifting her hand, “until the sun comes up, and then the light comes through the windows.”
And it occurs to me, in a quietly throat-knotting way, that in this little pocket of time we’ve spent together, what I’ve been seeing in Maggie isn’t a softness relative to her characters—it is a gracefulness relative to her life, as a mother, an artist, a survivor. The ability to let dark and light flow through her as needed, to remain open, stay buoyant, breathe.
Moments later, Lucy comes over and shows her mom a felt pouch she stitched for a friend, with the letter R and a purple flower. Maggie’s face blooms. Crafting is a family hobby, I’m learning. “My sister is a really big crafter, so I sometimes start to knit things when I’m up here, which I find very relaxing,” Maggie says. “I’m working on a sweater for Lucy. When I’m in the city, I don’t have the urge, but when I’m up here, I’m like, ‘Yeah, let’s try that. Let’s sew you a dress’ or things like that, that are not my natural métier or whatever, but up here, it comes out a little bit.”
We could keep chatting, and Maggie has kindly made me feel as if we have all day, but afternoon is calling. There are more secret swimming spots for mother and daughter to discover, and Maggie’s sister, the chef of the family, will likely be whipping up something delicious later, with Maggie relegated to making one of her creative salads, which suits her just fine. Plus, she has that sweater to finish. “It’s light blue, and it’s got a lot of … it’s like a lacy pattern,” she says, thoughtfully. “So, it’s pretty complicated, but I’m figuring it out.”
10 CHANGE-MAKING YEARS OF GIFF
Over the past decade, GIFF has recognized the courage and conviction of these powerful humanitarians and community- builders in our own backyard
2015
Mia Farrow
Harry Belafonte
2016
Abigail Breslin
Freida Pinto
Trudie Styler
2017
Christy Turlington Burns
Renée Zellweger
Andrew Niblock
2018
Ashley Judd
Duncan Edwards
2019
Eva Longoria
Connie Nielsen
Bobby Walker, Jr.
2020
Gretchen Carlson
Will Reeve
2022
Lin-Manuel Miranda
2023
Ty Stiklorius, John Legend, Mike Jackson
2024
Jerry and Jessica Seinfeld
SAVE THE DATE!
What’s happening?
GIFF’s 10th Anniversary Changemaker Gala
When: Wednesday, November 13, 7p.m.
Where: l’escale
Who’s being honored?
Golden Globe and Emmy-winning comedian Jerry Seinfeld and Jessica Seinfeld, founder of the Good+Foundation, bestselling author and executive producer of the award-winning documentary Daughters
What charity am I helping?
The Children’s Museum of Manhattan Family Connections Program, which reunites incarcerated parents on Rikers Island with their children to lessen trauma, strengthen bonds and reduce recidivism
Where can I get tix before it sells out?
Purchase tickets and tables at greenwichfilm.org