The Chicago Sky have emerged as significant winners in the WNBA free agency period, successfully re-signing key players and adding valuable talent to their roster. With the return of Courtney Vandersloot and the acquisition of other impactful players, the Sky are positioning themselves as strong contenders for the upcoming season.
Chicago has made significant strides during the 2025 WNBA offseason, positioning themselves as a team to watch in the upcoming season. With a focus on rebuilding and enhancing their roster, the Sky have successfully navigated the free agency landscape. Their strategy has involved acquiring key players while also making smart moves to secure future assets, including draft picks.
One of the most notable aspects of the Sky’s offseason has been their ability to swap first-round picks with the Phoenix Mercury. This maneuver not only strengthens their position in the draft but also allows them to capitalize on the Mercury’s uncertain future, especially with the potential departure of star players like Brittney Griner and Diana Taurasi. By securing a more favorable pick, the Sky have set themselves up for long-term success.
Additionally, the Sky have focused on adding experienced veterans to complement their young core. The signings of Rebecca Allen and Courtney Vandersloot are particularly significant, as both players bring leadership and skill to the team. Vandersloot’s return to Chicago is especially poignant, given her history with the franchise and her ability to elevate the play of those around her.
How Chicago Sky Won WNBA Free Agency According To ESPN
As it stands, Chicago has won free agency this year. This is detailed more in an analysis by Kevin Pelton for ESPN.
Rebuilding is an unattractive option for the Sun in part because they don’t control their 2026 first-round pick. Chicago has the ability to swap Phoenix’s first-round pick for Connecticut’s next year, and with the Sun’s stars heading elsewhere, that return suddenly looks far better for the Sky — particularly because the Mercury’s 2026 first-rounder now appears less valuable.
Chicago is rooting for Connecticut’s pick to land in the lottery because the Sky also agreed to swap their own first-round pick with Minnesota’s to get the 2024 draft pick they used on All-Star Angel Reese. With little incentive to lose in 2025, Chicago has built aggressively around Reese and fellow 2024 first-rounder Kamilla Cardoso, adding veterans Rebecca Allen and Courtney Vandersloot. All told, the Sky have to like how the offseason has gone.
As the Sky prepare for the new season, their blend of youth and experience could prove to be a winning formula. The team is looking to build on its recent successes while also embracing a new identity. With a solid foundation in place, the Sky are poised to make a strong push for the playoffs.
Chicago’s offseason moves reflect a thoughtful approach to building a competitive team. By securing valuable draft assets and adding experienced players, they have positioned themselves well for the future. As the season approaches, all eyes will be on the Sky to see how these changes translate into on-court success.
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