It was an honest mistake that resulted in an hour or so of waiting in line to vote. The executive director of the WNBPA, Jackson jokingly shamed herself for not following her own association’s advice to plan ahead when going to the polls.“The WNBPA’s been working with Rock the Vote for a while,” Jackson says while en route to a local church to cast her ballot. “And that’s really because there were many players, some on the executive committee like [Las Vegas Aces center] Carolyn Swords, who said we’ve got to be a part of voting.”
During the 2020 season ahead of the Nov. 3 election, the union promoted voter registration, and players around the league have been active in teaching young children about the democratic process as part of the Democracy in Schools program. In August, the players took their voting activism one step further by publicly endorsing Rev. Raphael Warnock, a Democrat and the challenger to Dream co-owner Kelly Loeffler, a Republican in the U.S. Senate.
This strong voice—the platform to speak up and speak out—is part of what Jackson envisioned for the WNBPA nearly five years ago, when she was appointed to her role. A professional league unlike any other.
But it wasn’t always this way. As 2012 WNBA champion, former WNBPA board president and current general manager of the Indiana Fever Tamika Catchings remembers at the time of Jackson’s hiring, there was a need for change.
“Her big thing that she talked about,” Catchings says, “was really being able to create an opportunity for all of us at that point in time, outside of what the WNBA was providing.”
One of the first and most pressing issues Jackson dealt with in her role as head of the WNPA was uniform violations. At first it was small things, like players being handed $200 fines for wearing a headband or a sports bra with a logo that differed from the official league sponsor at the time.
The matter got much more serious on July 9, 2016, when the Minnesota Lynx wore shirts that read, “Change Starts With Us. Justice & Accountability,” bore the names of police shooting victims Philando Castile and Alton Sterling, and honored the five Dallas police officers killed during the wave of protests that followed their deaths. The killings in 2016 deeply impacted the players, and they did not hold back in letting people know.
“People who had died of police violence that they knew of in their families or friend [circles], they were bringing that to the table. They were also talking about the people who had family members in the military or law enforcement,” Jackson says. “They were bringing all of that to the discussion and how what they were going to do was going to impact their families and their communities. And how they just wanted to get their arms around it.
“They wanted to be heard.”
But at the time, the league wasn’t listening. The shirts were in violation of the dress code—the WNBA instituted $500 fines per player and a $5,000 fine to teams directly—but there was more at stake for all parties.
“That felt like a muzzle,” Jackson says. “That felt like a We’re going to teach you a lesson kind of moment. I thought there was such an opportunity to do something different and for the union and the league to demonstrate a coming together to support the players in a more proper way. But that didn’t happen.”
After that, the Lynx players didn’t wear the shirts again, but other teams did, and the fines to the players and to teams kept coming. On July 21, 2016, Tina Charles accepted her Player of the Month award at center court in Madison Square Garden with her shirt inside out in protest against the fines, saying she would continue to use her “platform to speak out and raise awareness for the #BlackLivesMatter movement until the @wnba gives its support as it does for Breast Cancer Awareness, Pride and other subject matters.” After the game, she and her New York Liberty teammates and the visiting Indiana Fever held a media blackout, refusing to answer any questions that weren’t related to police shootings of civilians.
Just over two months into her new role, Jackson was faced with a very public battle between her players and their league. But she did not back down—after tough conversations with the league, the fines were eventually rescinded. For Jackson, it was a day with great significance on many levels.
“I started counting how many days I’ve been on the job,” she says. “It was 90 exactly. And it was my dad’s birthday. And I thought, Wow, I hope I made him proud because I was able to get this done.”
Jackson’s ultimate goal was always the court—the Supreme Court, in fact. As a child, she was determined to follow in the footsteps of her father, attorney LeRoy Carmichael, and go to law school. Eventually, her dreams evolved and Jackson had ambitions to become the first Black woman to serve as a Supreme Court justice. In pursuit of her career path, she attended Georgetown and ultimately met Jaren Jackson, her husband of 20 years and counting. After graduating Georgetown Law and working in D.C. while Jaren pursued a professional basketball career, Jackson took one of the first leaps of faith that led to her current position: She packed her bags and moved to New Orleans to start a nonprofit organization with Jaren.
“My path to the court, to the Supreme Court, was just changing,” Jackson says. “We talked a lot about working with young people and we started making notes and creating proposals for what a summer program could be. … It seemed like all the stars were aligning, that perhaps we should head south.”
Her father and mother, Eva Carmichael, who worked as a teacher and now serves as a court administrator in Middlesex, N.J., had raised their daughter to always have a solid plan—and this move, without a secure job, seemed like anything but that. Nevertheless, Terri persisted. “I just said, ‘No, we’re going to start this nonprofit. And don’t worry, everything will be fine,’” she says.
The summer program, called the Back on the Block Foundation, was Jaren’s way of giving back to his hometown while he was playing in the NBA. But it also was one of the first ways Terri expressed her passion to elevate girls and women in sports.
“She was determined to make sure that we had an impact on a lot of girls,” Jaren says. “I know my wife is passionate about doing something for young girls in sports, wanting to make sure that they have a fair shot just like the boys.”
It was Jackson’s first foray into the business of sports, but it would not be her last. While working at a law firm in Louisiana in 1996–97 and presumably on her way to the highest court of the land, she began researching Title IX. Before long she had a stack of case law articles so cumbersome it caught the attention of Jaren. After hearing Terri clamoring on about using her research to teach a class, he finally challenged her to just do it already.
In ‘98, after finding existing Tulane classes entitled Women of the Revolution and Women in Cinema, Jackson quickly decided on her course’s name: Women in Sports. Following more research, articles and preparation, Jackson met with Tulane administrators, ready to sell her class—except she didn’t have to. They were already sold. Jackson was officially a professor.
The year 1999 was a big one for the Jackson family. Terri began teaching, Jaren won an NBA title with the San Antonio Spurs, and their son, Jaren Jackson Jr., was born. Throughout his life, the Memphis Grizzlies forward has seen his mother’s fierce dedication to women in sports.
“My mom always would come up with these long-term ideas on how she wanted to better women in sports,” Jaren Jr. says. “And even if it wasn’t her main job—because she worked different jobs at the time—her long-term goal was women in sport and bettering them.”
While the Women in Sports course traveled with the Jackson family to San Antonio and Washington, D.C., Terri’s itch for the law was still burning. As fate would have it, Jackson got a lead about a position at the University of the District of Columbia to work as legal counsel for athletics. After accepting the position, Jackson found out that UDC had several compliance issues to tackle.
“It’s not a few things to follow up with. It’s a full-blown investigation,” Jackson says. “Every inch of the university is under the microscope. Admissions, financial aid, the athletic department, housing. Every inch of it.”
Jackson put all her research at the Louisiana law firm to good use. Her mastery at UDC as legal counsel for athletics and then assistant general counsel eventually led to four years at the NCAA headquarters as the associate director for the NCAA’s office of the committees on infractions, where she led the training on enforcement reform. In her last position at the NCAA before moving to the WNBPA, Jackson served as the director of law, policy and governance, where she was a primary contact and staff support for university chancellors, presidents and athletics administrators on the board of governors.
At first Jackson paid no attention to an email sent by a colleague sharing a WNBPA director of operations job at the WNBPA that they thought she should pursue. When that same colleague circled back, Jackson realized why the description had been sent her way.
“It’s everything I’ve been doing and wanting. It would be the next step,” Jackson says. “It’s governance, it’s advocating for women at the highest level in labor, it’s negotiation. … It’s amazing.”
Although Jaren Sr. did feel the timing and the role would be risky, he knew the family would support Terri regardless of where this opportunity took her. He thought back to the time Terri encouraged him to offer the same opportunities to girls that he did for the boys in his youth program in New Orleans. Sports was the hook, but the main goal was to empower the next generation to be leaders and entrepreneurs.
“I think every woman wants to have the opportunity to lead an organization,” Jaren Sr. says. “It’s exactly what we were telling young people in our camp, Back on the Block. One day you’re going to have to run something. You own your own business, lead an organization, be a head coach, make decisions for an organization. I think that’s what Terri and I were just meant to do.
And this opportunity to go out to New York and work for the players and WNBA, she just couldn’t pass up. And so we supported her, no doubt, no matter where we were.”
Once again, she diligently prepared.
“I know when she was going for different interviews for different positions and things, she would practice 800 million times,” Jaren Jr. says of his mom. “She’d go to great lengths to make sure she wouldn’t fail. She would have 20 different ways she could fail and she would cover all 20, and maybe only one would happen. But she was ready for all 20.”
He adds: “At the end of the day, she’s fighting against herself. There’s no one better than herself to her.”
Her preparation served her well through the final interview question, asked by Swin Cash, a three-time WNBA champion and the current vice president of basketball operations and team development for the New Orleans Pelicans: Where do you see the organization in five years?
“In five years, I hope that we are no longer comparing ourselves to the guys, that we are understanding who we are, what we bring to the table, the value we bring to the table, what our product is, and that it is different,” says Jackson of her response. “And that different doesn’t mean less than or more than, it just means different. And that we value different for what it is.”
It’s been nearly five years since Jackson was named as the WNBPA’s successor to Pam Wheeler. There has been a shift in how the union talks about progress, but comparisons to the NBA remain inevitable.
Yet, there are ways the WNBA and its union are pioneering—the creation of the Social Justice Council and the player-led initiative to have Black Lives Matter and other social messaging present in the single sites, or bubbles, for the 2020 seasons are prime examples.
“Some of the best CBAs I’ve ever seen in sports—not just women’s sports—are by her,” says Jaren Jr. of his mom’s landmark negotiations with WNBA officials, which this year resulted in a new, eight-year contract that secured players a 53% pay increase, paid maternity leave and fertility benefits, upgraded travel arrangements and more. “She’s trying to make sure her league and women in general have something they can take with them for a while.
“It’s not a short term thing. It’s not a money grab. It’s not a little here and there. She just thinks long-term and she’s given women a lot of confidence just to pretty much do whatever they want.”
Catchings agrees: “It’s been great seeing them be so forward thinking and pushing things so far. I don’t think that the WNBA and the PA have gotten enough credit for how much further ahead we are than a lot of other sports organizations,” she says. “And from our player standpoint, how each one of them continue to be the voice and continue to use their platform.”
Jackson and the WNBPA have also been able to establish a brand for WNBA players that is unique to them. That includes deals ranging from the new placement of the “Bet on Women” shirts in Dick’s Sporting Goods stores to the upcoming switch to Wilson as the official ball of the WNBA, to pushing for products that carry the names of all 144 players in the league.
In many ways, Jackson manifested her role as executive director of the WNBPA. The path took dips and turns along the way, but nearly five years later she’s just as excited—if not more—as she was on day one.
“What energizes me is working with women, knowing the power of women, knowing that with these particular women there’s a story that hasn’t been told,” Jackson says. “I have the opportunity to tell it, to showcase it and to make sure it’s done properly. It feels like, for the first time, we have an opportunity to course-correct. I’m just glad to be here in the moment to do that.”
For more from stories on the most powerful, most influential and most outstanding women in sports right now, check out Sports Illustrated’s series The Unrelenting.