When the Chicago Sky raise the banner marking the franchise’s first WNBA championship and seal it with a ring ceremony on May 24, Ann Crosby will see a dream come true — more than 15 years in the making. 

“She started out strictly as a strength and conditioning coach,” says Michael Alter, owner of the Chicago Sky. “Her job has evolved dramatically — the understatement of the century.”

Prior to joining the Sky, Crosby was the head strength and conditioning coach for the University of Illinois-Chicago’s 18 athletic teams, a job few women had. At that time, the Sky played at the UIC Pavilion. Crosby’s role meant she could be spotted at the Pavilion, on the court and bench, helping both the UIC men and women’s basketball teams warm up and stretch. It was during a 2006 UIC men’s basketball game that Altar and Georgia Fisher (then the athletic trainer and director of operations) approached Crosby about a job with the Sky.

Crosby had racked up a number of wins at that point: As a strength and conditioning coach, her professional career included championship titles at the professional and collegiate level, including a soccer World Cup title with Germany’s national women’s team. The thought of adding a WNBA title to her resume piqued her competitive spirit. 

But the championship eluded the franchise year after year. When the team drafted Elena Delle Donne in 2013, it marked the start of three consecutive years of playoff runs. The 2014 finals were particularly painful when the team was swept by the Phoenix Mercury in the best-of-five series. Yet Crosby stayed year after year, committed to doing whatever job was necessary to help the team succeed.

“I’m — unfortunately — a perfectionist,” Crosby says. “My family would ask, ‘Why are you still there? Didn’t you want to be in the NFL?’ and I’m like, ‘Yeah, but I haven’t won yet.’ It might take a couple of years, it might take some heartache, but I had not won at this level and I just couldn’t let that go.” 

This meant Crosby’s role grew to encompass whatever the team needed to thrive: Travel agent, surrogate mother, personal assistant, advocate, nutritionist, therapist, and more.

Nowhere was her do-it-all spirit more evident than in the physical rehabilitation of Diamond DeShields, guard for the 2021 championship Sky team who now plays for the Phoenix Mercury Sun. DeShields had to relearn how to gain control of her body after a surgery to remove a tumor from her spine left her with violent tremors and numbness in her feet. ESPN’s “Outside The Lines” recently revealed Crosby was one of DeShields’s caregivers and pillars of support on her road to recovery. Crosby spent hours alongside DeShields while she was hospitalized and assisted the guard during her rehabilitation to regain control of her motor skills. Less than a year later, DeShields managed to return to the court but she still had uncontrollable tremors triggered by heightened emotions. DeShields’s medical condition was not public at the time, so Crosby guarded her from the cameras and helped keep the player’s condition private.

“Ann is always, always working, and usually on behalf of somebody else,” Alter says. “Her commitment [to work] is as high as the highest level. She does it with such humility and servant spirit. She’s always smiling and always ready to step in and help.”

Despite how long it took to win a championship, Crosby says she never considered leaving, crediting the people in the Sky organization and the diversity of her work.

“It’s easy now, years later and with a championship, to look back and say that it’s worth it,” Alter says. “But at the time, (we’re) really fighting for something that you don’t know if and when it’s coming. What we’ve been fighting for is more than a championship. We’ve been fighting for credibility, for viability, to be taken seriously trying to demonstrate to everyone that these women are phenomenal and need to be valued and appreciated.”

The championship title, sold-out games at Wintrust Arena, and the bevy of famous names who came to root for the team — along with the announcement that the WNBA All-Star game is heading to Chicago — certainly signal a turning point for the team. But don’t expect Crosby to let it get to her head.

“At the end of the day, this is a job,” she says. “You have to act like nobody cares if you’re doing your job, as long as you’re doing (it). Just keep working harder to make things better.”

When the banner goes up and the rings are distributed on May 24, Crosby will make sure the players are warmed up and the rings are safely stored away so everyone can focus on winning the evening’s game. In other words, she will do what she always does: concentrate on the job at hand. 

“When you say Chicago Sky, you cannot not say Ann Crosby,” two-time WNBA MVP Candace Parker said during the team’s championship rally on October 19, 2021. “Ann Crosby is synonymous with Chicago Sky.”

With just a few words, Parker acknowledged the dedication of a woman who’s served the team for almost 17 years, and in that moment she gave her the gift of being seen, after so many years intentionally spent behind the scenes.

“It really means a lot that someone noticed. I don’t do this work to be noticed,” Crosby says. “To have someone of Candace’s nature recognize that was just…wow.”

And Parker isn’t the only one to note the effort Crosby gives to her work, which has arguably been one of the pillars of the Chicago Sky’s success.

“She’s an incredible hard worker, because she’s very focused on doing things right and doing them [at] a very high level,” Alter says. “There would be no Sky without Ann.”

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