When Courtney Vandersloot returned to Chicago after playing for two years in New York, her first stop was a familiar one for Sky fans: Portillo’s. The restaurant known for Chicago-style hot dogs and Italian beef has become a favorite for the team. Vandersloot’s favorite is a chili cheese dog. (Also this writer’s favorite.)
Back in 2021, Vandersloot sent a chocolate cake from Portillo’s to Candace Parker when the Sky were wooing the two-time MVP to sign with her hometown team. Vandersloot was drafted third overall by the Sky in 2011, but until then, the team had not been able to win a championship. The cake worked, and Parker and Vandersloot led Chicago to its first WNBA title that season.
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Since then, Parker signed with the Las Vegas Aces and then retired. Kahleah Copper, the MVP of the 2021 WNBA Finals, was traded to Phoenix. Vandersloot signed with the Liberty in 2023, and helped them win a WNBA championship in 2024.
The 2025 Chicago Sky team Vandersloot signed with during free agency is so different from the one she left. Tyler Marsh took over as the team’s head coach after Teresa Weatherspoon parted ways with the team after one season, and the team is loaded with young talent in Angel Reese, Kamilla Cardoso and Hailey Van Lith. But during Tuesday night’s preseason win over the Minnesota Lynx at Wintrust Arena, Vandersloot found that so much about the place where she played most of her career had stayed the same.
“It is so different and new, but it’s also so familiar, because it’s the Chicago Sky,” Vandersloot said. “The uniform, everything, the ownership, everybody is the same, but then we have this whole new team and staff. But I think that the right people are here, and so it feels like this is the right place. It feels very familiar to the team that I was on.”
Vandersloot wasn’t the only veteran added to the Chicago Sky’s roster. The team traded away its third-overall draft pick for Ariel Atkins, a two-time All-Star who helped the Washington Mystics win a title in 2019. They also signed Rebecca Allen and Kia Nurse, both WNBA veterans. Vandersloot knows it is her job to be a leader, but she isn’t the only one.
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“We’re surrounded with solid vets that are in their prime. And so I feel really good about my ability to kind of talk about my experiences, but people also have their voice,” Vandersloot said. “And so these young ones have a lot of people to learn from, and it’s not just going to be me. I think it’s natural for them to look at me first, but we have a lot of great voices that have a lot of good experiences on this team.”
Marsh, in his first year as a head coach, is grateful to have her voice on the court.
“She’s someone that leads by example first and foremost, but she’s not afraid to mix it up when she needs to as well. And I think that’s what a young team needs. She’s somebody that everyone respects from day one,” Marsh said. “And so she has that commanding voice and that commanding presence to where, when she speaks, she has everyone’s attention. And so that type of leadership is invaluable.”
As the Sky have so many new players, Vandersloot is using training camp to get to know her new teammates.
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“We’re all trying to figure each other out and learn, and you want it to be perfect. You want it to be great, because there’s such high expectations coming into it. We also understand that we have time, and we haven’t been together very long, and so it’s that stuff is going to take time,” she said.
Vandersloot is known for her passing. She’s behind only Sue Bird for the WNBA’s all-time assists record, and her single-game record was broken by Caitlin Clark last season. Vandersloot is able to thread passes into the smallest needle eyes. It’s a skill her teammates have to get used to so they are ready to score when she gets the ball in their hands.
“It’s kind of trial and error. I’m gonna throw the passes that I see open and then I’ve got to figure out, like, can they catch it? Is it going to put them in a good position to score?” Vandersloot said. “Because everybody’s a little bit different. I can give it to Kamilla late, really late, and it’s still going to be good. And I probably wouldn’t give it to Angel as late. She’s really good with the ball, and able to get it in her stride.”
The season doesn’t officially tip off for another week, but Vandersloot’s ties with her new teammates were clear during the Sky’s preseason games. Chicago hopes those connections will lead them to another title, and perhaps, another celebratory chocolate cake from Portillo’s.
