CHICAGO — For Skylar Diggins, the weeks of free agency leading up to her decision to sign with the Chicago Sky created a rare moment of reframing.
More than 80% of the league was out of contract in anticipation of the newly signed collective bargaining agreement. For months, every team took on an amorphous shape with no guarantees except for the players left on their rookie contracts. Players essentially were provided with a week to sit down with teams for serious discussions, then make a decision. Ahead of her 12th WNBA season, Diggins said this offered a unique situation to sit back and reevaluate the entirety of the league — and how she saw herself within it.
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After playing her entire career on the West Coast, Diggins wanted to come home. The guard grew up in South Bend, Ind., less than two hours from Chicago, and starred at Notre Dame. As the mother of 3- and 7-year-old children, Diggins felt herself drawn to the prospect of playing with family in the stands.
But the pitch had to be more than just proximity to home. Diggins, 35, wants to lead a team. More importantly, she wants to lead a winning team. To land their new starting point guard, general manager Jeff Pagliocca had to convince Diggins that the Sky and coach Tyler Marsh could provide that opportunity.
Diggins acknowledged the risk she’s taking by joining a team fresh off two losing seasons — “A little bit of it is a leap of faith,” she said — but didn’t waver in her confidence.
“I’m bought into the vision,” Diggins said Wednesday during an introductory news conference at The Metropolitan. “I’m not just coming here saying this is the end or whatever for me. I want to play some good basketball. I still have a lot to go as far as what I feel like I can do, especially with this team.”
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Pagliocca was incredibly high on the team’s prospects for landing free agents, but Diggins is experienced enough not to put too much stock into the hopeful projections of a front office before the negotiation window actually has opened. The guard felt confident enough investing in the foundation of the Sky’s plan, which centered on a partnership with center Kamilla Cardoso.
But as free agency opened, Diggins also gained additional confidence from the prospective players the Sky seemed poised to acquire. She shares an agency with Rickea Jackson, which gave her an inside track on the possibility that the forward might be traded to the Sky. And Diggins also knew that forward Azurá Stevens was dead set on signing with the Sky long before free agency opened.
“She was telling everybody pretty much that would listen that she was going to Chicago,” Diggins said with a laugh.
When all the chips fell, Diggins ultimately felt Pagliocca had succeeded in assembling a competitive roster that made sense with herself at the helm. The Sky prioritized two-way players, which fit the defensive-minded approach Diggins brings to the game.
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The guard also feels the Sky landed on the correct balance of personalities in the roster. She knows her reputation as a commanding team captain who isn’t afraid to confront coaches or teammates when a team is falling short.
“Everybody that knows me knows I challenge my teammates around me,” Diggins said. “I wouldn’t say I’m an easy teammate, but I’m a good teammate because I’m going to challenge you.”
On this roster, Diggins trusts that this leadership style will be met with enthusiasm — and that her fellow veterans can help to set and enforce that standard.
Fellow point guard Courtney Vandersloot is similarly demanding of both herself and teammates. Guard Rachel Banham brings levity to a locker room. Center Elizabeth Williams is “always the adult in the room.”
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“We’re not a monolith,” Diggins said. “We need the diversity.”
Diggins knows leadership will be necessary to reestablish the Sky as a competitive team.
They won only 10 games last season. They won 13 games the year before that. The Sky have not made the playoffs since the 2023 season. On the court, they visibly struggled to create any cohesive style of play while cycling through three coaches in three seasons.
But Diggins believes that can change — and quickly.
“Our standards have to be strong,” Diggins said. “Because if we have strong standards, then that demands respect. We’re not going to get punked. I’m the chief of security right here. It’s just our identity. Who are we going to be?”
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This free-agency cycle was also a crucial first step in recalibrating player perception of the Sky as an organization. For years, the franchise has struggled to attract free agents and retain top talent. The construction of a new training facility will help to alleviate some of those concerns, but the Sky’s problems went deeper than resources.
Marsh said this required the team to start “tough conversations that have been had behind closed doors” and make internal adjustments as a result. Pagliocca said Sky ownership spent the offseason working to invest in continued improvements that would make the team a free-agent destination well beyond 2026.
This resulted in an explosive free-agency cycle — with Diggins at the heart of it all.
“Players are aware of the negative things that get said on the daily,” Marsh, 38, said. “We’re all engaged in social media. We’re aware of it. But Skylar’s been around this league a long time to know the fake from the real. There’s a reason why she wanted to be here. Being close to home helps, but you’ve also got to be able to trust the people that you’re going into war with.”
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