Penny Toler learned to play basketball on the streets of Washington, D.C., at seven years old. Most of the time she was the only girl on the court—a circumstance that helped her to learn an important rule early on. “If you weren’t tough, you weren’t playing,” she says.
That toughness, along with serious skill, led to a number of historic firsts: In 1997 Toler was drafted by the Los Angeles Sparks, where she became the first player to score in the brand new WNBA.
After retiring from the game in 1999, the former point guard joined the Sparks’ front office as the club’s first female executive vice president and general manager, and she is one of only five female G.M.s in the WNBA today. (Even in women’s professional sports, men still dominate front-office and executive roles.)
“The day it’s not fun anymore, I’ll pass the torch and walk away with extraordinary memories.”
After 19 years Toler, 52, is both the longest-tenured and winningest G.M. in WNBA history. “A lot of people weren’t happy when I was made general manager,” she says. “I said to myself, ‘I will not fail.’ This is about other African Americans, other females, other athletes getting opportunities after me.”
She sees the WNBA as a training ground for a new generation of female leaders. “I’m happy to be able to say I was the first to do what I did, but the WNBA has produced a lot of people who have been a lot of firsts,” she says.
And while she’s not slowing down any time soon, she knows when she’ll be ready to hang up her basketball shoes. “The day it’s not fun anymore, I’ll pass the torch, and walk away with extraordinary memories.”
For now, here’s what a typical home-game day looks like for Toler.
5 a.m. Toler starts with a brisk, three-to-five-mile treadmill sesh at the gym in her downtown building.
7 a.m. Back in her apartment, she answers urgent emails—always with the Today Show on in the background—before heading to Staples Center.
9:30 a.m. Toler stops by practice at Staples and hangs out for a game-day shootaround.
1 p.m. Time for a one-on-one meeting with Michael Fisher, assistant GM, to talk logistics. “I’m ultimately responsible for contracts, schedules, travel—everything that comes with the team—so that’s all in the mix,” Toler says.
3 p.m. Toler meets with Sparks senior VP, Natalie White, to discuss everything from the team’s community relations to its ticket sales.
4 p.m. She writes up an overview of her meeting with White to send to owners Eric Holoman, Stan Kasten, and Earvin “Magic” Johnson.
7:30 p.m. After a final check-in with the trainers and coaches, Toler takes her seat in Staples Center and focuses on the court. “Once the game starts, my job is to pray we win,” she says. “Everything else is out of my hands.”