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Rainmaker. Boss. Baker. Meet Tamika Tremaglio, the new head of the NBA players’ union.

Tamika Tremaglio started her four-year term as executive director of the NBA Players Association in January. (Jesse Dittmar for The Washington Post)
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NEW YORK — Growing up in St. Mary’s County, where the Potomac and Patuxent rivers meet the Chesapeake Bay, Tamika Tremaglio loved the water and the southern Maryland woods, but nothing moved her quite like cash register tape.

Tremaglio, the new head of the NBA players’ union, was born two months before her mother, Pamela Langley, enrolled at Morgan State University as an 18-year-old freshman. With grandmothers and aunts stepping in to help care for Tremaglio, it wasn’t long before she was helping to keep count in her uncle’s tire shop and her family’s bars.

“I love puzzles and problem-solving,” Tremaglio said during an extended interview Jan. 20 at the National Basketball Players Association’s Manhattan headquarters. “I was raised by a family of entrepreneurs and have always dealt with numbers. I’d check the cash register sheet and try to find an error, down to the decimal point. Numbers were the way to solve problems. They were the key.”

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Numbers have driven Tremaglio’s professional life, from her decision to pursue a law degree from the University of Maryland and an MBA from the University of Baltimore to her career at Deloitte, where she served as managing principal for the global accounting behemoth. In January, the 51-year-old stepped in as the NBPA’s executive director at a time when finances are top of mind given pandemic-related losses and the extraordinary growth in media rights revenue, player salaries and off-court investment opportunities over the past decade.

The NBPA’s executive director has traditionally been cast as a firebrand and a bulwark against owner overreach during labor negotiations, and both sides have the ability to opt out of the collective bargaining agreement following the 2022-23 season. While Tremaglio will take the lead on the next round of talks, her new constituents have tasked her to play rainmaker in the meantime.

“Her business background is what we need,” said Portland Trail Blazers guard CJ McCollum, the union’s new president. “It’s the next step in our evolution — not only ways to manage and save our money but ways to grow it. She puts us in position to think more like CEOs, and creating more revenue is always at the forefront of our conversations. We’re looking at where the world is going with streaming devices, gambling, technology, crypto. Ten years from now, who knows, there might be games being played in the metaverse.”

Gentle touch

Tremaglio, a lifelong D.C.-area resident, was still adjusting to her new Hell’s Kitchen digs when she made quite the first impression with her new colleagues. Longtime union employees were stunned when the executive — who has a penchant for designer business attire, tasteful jewelry and high-end heels — brought in two oversize sacks filled with pans, bowls, utensils and boxes of ingredients during her first week on the job.

“She was dressed to the nines with an apron,” said Chrysa Chin, the union’s executive vice president for strategic engagement and development. “She’s engaging with everyone while she’s cooking frittatas and sweet potato waffles all by herself. She came in as the equivalent of a B12 shot. She just injected all this energy.”

Brunch was only the beginning. Word began to spread that Tremaglio; her husband, Greg, a retired special agent for the Treasury Department; and their teenage sons ship out 300 homemade rum cakes to family and friends each holiday season. At an office icebreaker, Tremaglio circulated make-your-own-margarita kits in packages that bore her new slogan: “Reimagine the possible.” And the new boss gifted custom Dolce & Gabbana sneakers to select senior employees, with each pair bearing inspirational titles such as “game-changer.”

“What she wears to work out is probably better than my best suit,” said Ron Klempner, the union’s senior counsel for collective bargaining. “She has this way of turning everything positive. In our first meeting, she asked us to describe our superpowers. I said ‘survival’ because I’ve been here so long. She flipped it and called it ‘resilience.’ It’s just delightful and empowering.”

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Under Tremaglio’s predecessor, Michele Roberts, the NBPA grew from roughly 25 employees to nearly 100, riding the wave of basketball’s most lucrative era. When Roberts became the union’s first female leader in 2014, her chief task was to restore order after allegations of corruption during the previous regime led by Billy Hunter.

Together with former union president Chris Paul, Roberts successfully negotiated a new CBA in 2016, created a health-care program for retired players and oversaw modified labor agreements that have kept the sport going during the pandemic. But the 65-year-old Roberts, who had started to make plans to retire in early 2020, stayed on through December 2021 out of a sense of obligation to the union. Business had been disrupted, and high-profile players were drawing criticism for everything from their political activism to their vaccine hesitancy.

That delayed transition, which covered multiple exhausting seasons, created an opening for Tremaglio to make her mark with enthusiasm and new ideas. During the job interview process, which concluded in September, Tremaglio beat out dozens of candidates by stressing her financial savvy and familiarity with professional basketball, including her work on the accounting team that investigated Hunter’s tenure and her contributions to the WNBA’s recent labor negotiations.

The time was right for a career move; Tremaglio was eligible for retirement at Deloitte and felt she had “done what I needed to do” during 26 years in the consulting world. She viewed the union as an opportunity to channel her legal and financial experience into a position where she “could make an impact” by guiding an organization that has made headlines for its social justice efforts.

“Michele leaves big shoes to fill, but for me it’s about walking my own steps,” Tremaglio said.

In contrast to Roberts, a steely attorney who famously warned that her “past is littered with the bones of men who were foolish enough to think I was someone they could sleep on,” Tremaglio prefers a gentler touch. The former high school and college cheerleader still identifies as a “cheerleader for basketball today” and roots for the Washington Wizards and Mystics. While an undergrad at Mount St. Mary’s in the early 1990s, she happened to teach step aerobics to several players from the then-Bullets, who were brought to campus by former owner Abe Pollin.

Tremaglio’s core optimism and Catholic faith have shaped what she calls her “servant leadership” philosophy, which involves listening to her clients, assessing their needs, researching solutions and seeking outcomes that are based on “being good rather than being right.” When Lady Gaga’s Born This Way Foundation launched its “kinder, braver world” campaign, Tremaglio sat on the board, one of 11 that she worked for while at Deloitte.

“Disagreements sometimes come down to ego,” she said. “That’s not me. What’s important to me is that I’m protecting the rights of the players in a way that is really respectful and leaves everyone’s dignity intact. It’s not critical for me to destroy people.”

Yet McCollum left Tremaglio’s job interview confident that she “has it in her to be an assassin,” a prerequisite for high-stakes negotiations in a league that projects to generate $10 billion in revenue this season.

Terri Jackson, the head of the WNBA players’ union, recalled Tremaglio’s unapologetic persistence as they successfully pushed for a more equitable revenue sharing model during the WNBA’s 2020 labor negotiations. Tremaglio prepared extensive financial models to guide the talks while taking Amtrak from Washington to New York, then hammered home a point so effectively during one bargaining session that a rival negotiator admitted in a subsequent meeting that he still had “Tamika’s voice in my head.”

“She got in his head, and he basically exposed that,” Jackson said. “I honestly couldn’t believe he said it. She’s brilliant, poised and laser-focused on negotiations. I absolutely wouldn’t want to be on the other side of the table across from her. [The NBA] hasn’t seen what a force she is. She’s disarming with her style, but she is unrelenting. If you miscalculate who she is, well, I feel sorry for you.”

Grand ambitions

Even before the pandemic, NBA Commissioner Adam Silver eschewed the combative style of his predecessor, David Stern, in favor of pragmatism and “partnerships” with the league’s players. Three seasons of intense bargaining and emergency planning have forced the two sides to seek even more common ground as they constructed the Disney World bubble, worked through schedule disruptions and held games in empty arenas. So far, the early warning signs that preceded past lockouts in 1999 and 2011 have yet to materialize.

“Michele came at a time when we were still feeling the effects of labor strife,” said Klempner, who joined the union in 1993. “People were looking for a strong, tough personality who would stand up to David Stern and the owners. Michele reflected that. We’re now at a time from a labor perspective where things have stabilized, hopefully. We spent a fair amount of time together [with the NBA], and you have no alternative but to become closer. There’s a good sense of trust.”

Still, there are plenty of meaty topics for discussion during the next talks, including how to split revenue between the owners and the players, how to handle disruptive trade demands such as the one made by Philadelphia 76ers guard Ben Simmons, how to tweak the luxury tax system and whether to alter the “one-and-done” rule that prevents high school players from entering the NBA draft.

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Tremaglio credited Roberts with passing on an “incredible relationship” with the NBA, and the union is hopeful that the short-term negotiations prompted by the pandemic won’t be necessary after this season. Although Tremaglio pledged to avoid “negotiations through the media” whenever possible, she revealed that she has shared her top three priorities with Silver: finding additional revenue opportunities for players in the CBA; forecasting basketball’s future to prepare for changes to media consumption habits and other technological advancements; and supporting players’ mental and physical health during and after their careers.

One recurring point of contention during Roberts’s tenure concerned the dramatic rise in franchise valuations and sale prices, with the players arguing that they weren’t sharing in the rewards despite helping to drive the increases. Roberts recently asserted that players should be given some level of equity in the franchises to address the situation, and McCollum said Tremaglio has already discussed the subject internally.

“Equity is how you build real wealth,” he said. “Tamika talked about it. There’s a difference between players making good money and ownership groups having money. We want to get to the point where players have money, too. It’s not just equity in our teams but in other businesses, too. It’s crazy that we’re not able to invest alongside the ownership groups in independent deals.”

The success of Tremaglio’s tenure is likely to be determined by how well she fulfills the players’ grand and growing ambitions. As she sat in a gleaming conference room, she thought back to her mother’s decision to press on with college despite having a newborn daughter. In the years that followed, Langley dispensed simple but demanding advice: “If they’re walking, you need to be running. If they’re getting B’s, you need to get A’s.”

Tremaglio then listed the many ways those words still shape her life, noting that she drills her own sons, Rocque and Reece, on the importance of striving to be “amazing” rather than “good.” She has completed two marathons and tracks her daily activity with a Fitbit and an Oura ring, regularly hopping on a treadmill to multitask during virtual meetings. For exercise, she favors a Peloton bike or a Hydrow rowing machine because both will score her workouts.

“I have always loved competing,” she said. “I always loved school because I loved being graded. For high achievers, an A-plus means you did all right. If you get 10,000 steps in, you did all right. It’s this constant thing.”

This train of thought triggered a memory: Tremaglio had come across a piece of art depicting a woman bound in measuring tape. The image was unsettling because it felt like a mirror, but the feeling passed.

In a battle against her numbers, doubt didn’t stand a chance.

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