Last month, on her fourth day as the National Basketball Players Association’s executive director, Tamika Tremaglio laid down a new rule for her senior management team. They would spend the next 21 days without saying no to a thing.
This was the beginning of a mental remodeling for her staff and an organizational rewiring by its new leader. She is asking them to change, just as she has in recent years after fighting self-doubt to come out with a new model of leadership.
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Nothing was too small to agree with — not in IT, not in infrastructure. She wanted them to start thinking differently, to think through all of the possibilities on an issue before they leaned on the same archetypes they had constructed after years in their jobs. After the full three weeks, she hoped it would become a habit.
Tremaglio has come to the NBPA with change in mind. It’s been her driving mission as she sought the job and, now, as she imagines what she can do with it.
She comes with connections, with verve, and eyes set on updating the NBPA. While she spent her career at firms outside of professional sports, she is no outsider, having consulted for several unions across leagues.
Tremaglio approaches her new role with optimism and uplift. She speaks melodically — hypnotizing in her ability to place disparate ideas into one train of thought. Michele Roberts, her predecessor, first met her years ago when she needed an expert witness. She set out to hire a more senior person but chose Tremaglio instead because of her ease expressing information in a way that would win over a jury.
“Her ability to really solve complex problems, to be creative, to build relationships, to see around corners or look over the horizon,” Donald Remy, the Deputy Secretary of Veterans Affairs and someone who has known her a while in their familiar Washington, D.C., circles, said. “Her business acumen is significant. That’s what puts her in a position to be successful.”
In its new executive director, say people who know her well, the NBPA has hired a brilliant thinker, a strategic mind, and a considerate soul. Her kindness is her calling card and a weapon. Friends rave about her cakes, delivered each Christmas — in 2020, she sent its ingredients and instructions — and now NBPA officials and its executive committee players gush about them, too. But Tremaglio’s sweet mien also lures in the people sitting across from her, say those who have witnessed her at work; a sugary trap for the unprepared.
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Tremaglio is the third Black woman to run a professional sports union in North America, following in the footsteps of Roberts, who was the first. When she first laid out the idea of leaving her job as managing principal of Deloitte’s D.C. office to head the union, Tremaglio told friends it was because she believed she could be a gamechanger. During her interviews with the NBPA’s executive committee, she called herself a transformational leader.
The league’s players deserve someone who could help them accrue generational wealth, Tremaglio thought, who could help them achieve equity, and she would be the one to do it. For her, the job mattered. As her friends attest, once Tremaglio sets her mind to something there is little chance of changing it.
“This was my sweet spot, to be able to do that,” she told The Athletic last month during a lengthy conversation. “It’s also a way to solve problems and try to figure out how to do things differently and uniquely. As part of that part of my theme in coming to the NBA is reimagining the art of the possible. What is it that we can do? Not focus on what has historically happened but rather let’s focus on what are all of the possibilities?”
Tremaglio took over Jan. 10 and set about trying to move the NBPA into her image. She took over in the midst of a storm, as COVID-19 once again ravaged the league. While that has since passed, other problems may soon arise.
She comes in at a time of comity between the union and the NBA, endowed by Adam Silver and Roberts. But decisions loom. Either side could opt out of the current collective bargaining agreement — set to expire after the end of the 2023-24 season — as early as next December.
But her job will not just be about the next CBA — as substantial as that is — she has been entrusted by players to bring economic growth and to transition it smoothly through a quickly changing commercial landscape. They chose Tremaglio, who holds both an MBA and a law degree, for her combination of financial and legal wisdom.
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She’s also a velvet glove, Sunny Hostin, a longtime friend said. Behind Tremaglio’s cheery disposition is a stout negotiator and one the NBA would be wise not to overlook.
“When you see her in the boardroom she changes what you would visualize if somebody told you ‘OK, imagine the Chair of a board,’” Ava Lias-Booker, another friend, said. “First of all, you’re probably going to think it’s a man, or a white man. After you experience Tamika you will no longer think like that.”
The NBPA’s search for a new executive director was exhaustive. The union set out for its successor to Michele Roberts before the onset of the pandemic and did not complete it until about a year and a half later. More than 120 candidates were considered; among them were ex-players, sports industry executives, lawyers and even former government officials. The first round of interviews featured 40 interviews. The executive committee had lengthy meetings with 20 of them. Tremaglio interviewed three times.
She centered her pitch around three key issues: increasing business opportunities for the union, reconsidering the future of work for its players and a focus on their protection and development. Her scope was far-ranging, from the ways to increase revenue through BRI or Think450, the NBPA’s for-profit arm, to asking them to consider what the future of basketball will look like, to a focus on mental health, which she alerted is already being dubbed the second pandemic.
“In general, how our players are perceived and thought of in the marketplace,” Tremaglio said. “All of these men are brilliant. They have been entrepreneurs, many of them since the age of 8 as independent contractors trading from AAU team to AAU team. So how are they continuing to get the right exposure to develop that?”
Tremaglio’s last interview came on Zoom in September, in front of more than 60 players, including representatives from each team. She had a PowerPoint presentation, which was so rare that she might have been the first to use one. She impressed them with her presence and her road map for the union.
Tremaglio made a forthright pitch. The job she was seeking is not glamorous, she told players according to a person with knowledge of the call; it needs someone who can fulfill its quotidian demands while also standing as a public face for the union and its lead negotiator and as a strategic thinker. Garrett Temple, an NBPA vice president, summed her interview up: “It was amazing.”
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She won the position by unanimous vote.
The voting bloc was already familiar with Tremaglio before the search began. She had come into it as a quasi-insider.
Tremaglio led the forensic accounting unit the NBPA hired after former executive director Billy Hunter was fired in 2013. Roberts hired her in recent years for an overview of the union’s organizational structure. (Roberts says she remained neutral during the search.) She was a critical part of the WNBA negotiating team during its 2020 CBA agreement — the two unions share close ties and WNBA players sat in on interviews during the NBPA’s search.
That history with the NBPA gave players some comfort with her. Her time running the office at Deloitte, with more than 14,000 people, offered the managerial experience they sought. Her background in law and business gave them ease that she would bring the legal and financial chops they needed.
What won Tremaglio the job with the NBPA is also what has earned her acclaim from her friends and colleagues. She is lionized for her unceasing warmth and an endless reserve of energy. During her time at Deloitte, she also sat on the board of the Born This Way Foundation and the WNBPA Board of Advocates.
Tremaglio finds a way to build relationships and maintain them for the long haul. She has been friends with Stephanie Rawlings-Blake, the former Baltimore mayor, and Hostin, now a co-host on The View, since law school. Both now sit on the WNBPA board after her urging. Back then, she turned heads for her gregariousness and certitude, just as she does now.
She hasn’t played basketball but says she has a long history with it. She was a cheerleader in high school and at the University of Maryland, but now says she considered that role to be an ambassador for the sport, and her entry into it. Deloitte owned a suite in D.C. for Wizards and Mystics games and Tremaglio was often there as the managing partner.
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Tremaglio believes the job she is taking on now is not much different than the one she held. While she worked for more than two decades as a forensic accountant and led global investigations, she says her time at Deloitte provides an analog to the NBPA. There, just like now, she worked at a partnership. When she took over as managing partner at Deloitte, she tried to make the company’s various firms work together instead of in their separate silos. Her job, she said, has boiled down to one issue over the past 26 years: problem-solving.
She played an integral role for the WNBPA as it negotiated its recent CBA. Nneka Ogwumike, the WNBPA president, said Tremaglio’s work was invaluable.
Tremaglio wore multiple hats during the lengthy process. She served as a sounding board for the players and helped elucidate what they wanted out of the agreement. ”She never made us feel as though nothing was impossible,” Ogwumike said.
Ogwumike said Tremaglio was able to center the negotiations for the players and bridge what the union wanted and what it could expect from the WNBA. In the summer of 2018, before the players opted out, Tremaglio created and ran the players through a model that explored what they could gain in a new CBA.
She also served as devil’s advocate, giving what she thought would be the WNBA perspective — her former Deloitte colleague and friend, Cathy Engelbert, is the league’s commissioner. (Engelbert was not made available for this story.)
“It made our negotiations not feel like divorce court,” Ogwumike said, “but like two groups who want the same thing but see things differently.”
Terri Jackson, the WNBPA executive director, credits Tremaglio for helping the union rethink what the league’s revenue share could look like. It had previously been tied to team ticket sales. Tremaglio suggested that it be scrapped and tied to the league’s business instead, which would expand the pot. The new provision, Jackson said, was authored by Tremaglio.
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Occasionally, Tremaglio left the WNBA representatives on tilt. At one bargaining session, when Tremaglio was not present, a WNBA staff member complained that he still had her voice ringing in his head from their last meeting. When Jackson relayed the story to Tremaglio, she laughed. “‘Great,” Jackson said Tremaglio told her. “That means I’m getting to them. I’m in their head.’”
Now, Jackson is excited that Tremaglio will lead the NBPA, where Jackson’s son, Grizzlies center Jaren Jackson Jr., is a player rep. Her assessment of Tremaglio after their experience in putting the WNBA’s latest CBA together, which brought major gains to players in salary and benefits: unflappable and brilliant.
“She is very, very polite, respectful, but she is firm,” Jackson said. “She walks into the room a thousand percent prepared. She has combed through very meticulously and she’s prepared. Even when it’s that 12th hour, when you have to pivot, she’s ready. It was a complete sense of comfort knowing that that’s who she is, that that’s her approach, and that’s who is sitting right next to me at the table.”
Tremaglio takes over the NBPA at a time of tumult brought on by the pandemic and the shockwaves it has brought to the league’s finances, but also of labor peace. The league and the union negotiated their last CBA in relative calm. Silver and Roberts had a strong working relationship, without the fireworks of their predecessors, and the collegiality between the two sides is unmatched in any of the other major sports.
Tremaglio seems uninterested in disrupting that. After she was named the incoming executive director, she went on a listening tour of the league’s agents, joined in on team NBPA meetings and met with her future staff. But one of her first dinners was with Silver.
“Tamika and I have had several productive conversations since she took over as executive director,” Silver said. “She is highly engaged and passionate about her role and well-versed in the business of the league given her prior experience as an adviser and consultant to the PA. I am looking forward to working closely with her to build on our strong partnership with the players.”
The league and union each have the ability to opt out of the current CBA at the end of this year. Tremaglio’s intent is to operate in a way that is least disruptive to everyone involved.
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“There is no benefit for any of us to opt out,” she said. “There is always the opportunity for us to work together. I do think Michele has been able to build a really great relationship with the league and I cannot see that not continuing. I think Adam has been incredibly welcoming. Michele helped to set up a really great transition for me. I think I’m coming in at a time that is needed, for certain, but I also feel I am coming in at a time that we can continue the path that we have already been on. Which is the path certainly of least resistance and much more partnership in terms of what we can accomplish.
“We’re not back in the ’60s where we’re looking for ways to be adversarial to each other. We recognize that we can get more done together.”
As a law student at Maryland, Tremaglio earned the highest grade of anyone in the school who had taken a class on negotiations that semester. She didn’t think that talent would help her in the future.
But Tremaglio has won acclaim for her negotiation skills. Ogwumike briefed NBPA president CJ McCollum on her during the search. Those who have seen her work say she has a unique style that is hard to describe.
Lias-Booker, a partner at the white-shoe law firm McGuireWoods, used to sit on the Maryland Law School board with her. After one meeting discussing a new scholarship program, Lias-Booker was so enthralled that she sent Tremaglio a note afterward. It was wonderful to behold you in there, she told her.
Tremaglio said her tact is to remember that both sides are looking for something, instead of embracing unilateralism and ego.
“It is really critically important that I am not coming from a place where I want to be right,” she said. “Oftentimes, when I recognize that people are having disagreements it’s because one person has to be right and one person has to be wrong, as opposed to being good and focusing on what you want the outcome to be.”
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The CBA was the primary concern for players during their search, Temple said, and Tremaglio will be in a negotiating posture sooner than later. The NBA will also need to adjust to her. She brings a new dimension to their conversations; people who know Tremaglio and Roberts remark how different they are in personality.
While Tremaglio comes into the job hoping to change the NBPA, she steps into it having undergone her own transformations over the last decade. She took the first real vacation of her career while at Deloitte, realizing the importance of time away. She also embraced her affliction with imposter syndrome, which caused her to doubt her success and her place.
Tremaglio reached out to Joyce Roche, a former high-powered executive who wrote ‘The Empress Has No Clothes,’ a book about overcoming that self-doubt.
“The reason why it really connected with me is because I thought I was the only one who would show up in the room as the only female or as the only person of color and thought, ‘Oh my gosh, they’re going to figure out that I don’t know every single thing in the world’,” she said. “To hear someone like her who was a C-suite executive … to actually feel like that, that was sort of a relief.”
She turned introspective after conversations with Roche. They allowed her to be public about her own concerns. Tremaglio started bringing Roche in to speak at Deloitte events and they did roadshows for women at the company. Tremaglio asked other senior women at Deloitte to write letters to their younger selves and she shared her story.
Roche noticed an evolution since they first met in 2013. Tremaglio has grown more comfortable with herself and displaying her authenticity, she said — something Tremaglio admits.
“When I first had this conversation at Deloitte, it was with a group of women and it was a game-changer for me,” Tremaglio said. “Because oftentimes, people felt like, as leaders, we are unapproachable and there’s nothing that we could have in common with them, and then to let people know that you have your own insecurities and that you felt the same way that they did, it actually allowed people to then show up authentically as well. Quite frankly, I’ve learned from people that I’ve become more approachable to them because they feel like there’s something we can relate about or we can talk about. Letting that guard down lets other people in. It also makes you a lot less defensive when you feel you have to defend everything that you’re doing when you realize some of it is your own insecurity.”
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She believes these last few years have been transformational. That led her to seek a new course, and to continue on with that growth.
During the pandemic, Tremaglio reflected on her next career step. She wanted to make an impact. She wanted to do something that was important. The executive director of the NBPA mattered, she believed.
Now she intends to move the NBPA through to its next phase. The revamp has already begun.
“The biggest mistake that any change-agent can make, quite frankly, is imposing it on someone,” she said. “They have to come to it on their own; I can only bring them to where I would like us to be.”
(Top photo of Tamika Tremaglio courtesy of the NBPA)
