Sky’s ‘superwoman’ Ann Crosby plays double duty

If Ann Crosby was stressed, she didn’t show it.

Standing at the United Airlines desk at O’Hare International Airport, Crosby, the Sky’s director of basketball operations who doubles as the team’s strength and conditioning coach, was trying to rebook flights to Hartford, Connecticut, for a party of 18 after the team’s first flight was cancelled.

Everyone was starting to get irritable, and time was of the essence because their important game against second-ranked Connecticut Sun was less than 24 hours away. The group was put on standby for the next flight out, but it had already been overbooked.

“It’s one of those things, unfortunately you just have to keep everybody in the loop,” Crosby said. “‘Hey, here’s what could happen next. I’m sorry, keep waiting, keep waiting.’”

The first group got on a flight. The rest were forced to wait.

A terminal change and more than nine hours of finger twirling later, the second group finally boarded a plane just before midnight.

That was an extremely trying day — and it only got worse when the bus was a no show after the team landed at 3:30 a.m. — but Crosby has large-group traveling down to a science at this point.

“The biggest thing is always having a Plan B,” said Crosby, the Sky’s longest-tenured employee. “When a bus doesn’t show up, I’ve got car companies in each city that I can call, and try to go from there. If not, Uber is a great way. And then, obviously, turn around and scream at the bus company after that.”

While coach James Wade and point guard Courtney Vandersloot might be two of the most recognizable faces of the Sky, Crosby is the team’s backbone. The Sky have five members in their operations department, compared to the Bulls’ 32, and Crosby, with the help of interns, is responsible for the work of about 25 people.

“If you need something done, Ann is probably going to be involved in it at some kind of capacity,” Wade said. “She knows everybody and if there’s anything off the court, she probably knows. And if she doesn’t know how to get it done, she knows the person that knows how to get it done.”

Crosby does all this while being the mother of two kids under 12 and leading the team’s stretches and workouts.

“I call her ‘superwoman,’” forward Cheyenne Parker said. “She has to pretty much book all of our flights, all of our hotels, everything. Our cars being shipped, even personal flights, she does it all, literally, as far as being there for us, like she’s literally the team mom.”

How does she manage it all?

“One day at a time,” Crosby said.

WNBA players are often surrounded by unfamiliar people — both with their overseas teams and in the U.S. But Crosby is a constant for the Sky, and that’s so important to many of the players players like Parker, who has Attention-deficit/hyperactivity disorder and suffers from depression and relies on her for professional and personal support.

“She’s always intuitive,” Parker said. “She was able to pull me out of my funk a few times and give me a few words of encouragement.”

“Through my trials and tribulations of that, it helps me relate to the players but having someone who is consistent time after time does say something about our organization as a whole,” Crosby said. “And the players they go overseas, they’re in different countries, they’re on different teams every year for the most part, so there isn’t much consistency in their life and I try to offer them that as much as possible.”