WNBA free agency: Could Sky land top free agent Skylar Diggins-Smith?

By Chicago 4 Min Read

Three months away from the beginning of WNBA free agency, rumors are already swirling around the Sky.

Considering their salary-cap space and one particular free agent — Skylar Diggins-Smith — it’s understandable that the idea of the two sides coming together is atop the fans’ wish list. The question is whether it’s plausible.

Considering the Sky’s needs — a reliable starting point guard is the first priority — the idea makes a lot of sense.

Courtney Williams will be an unrestricted free agent in January after signing a one-year deal with the Sky last year. She was tapped by former coach/general manager James Wade to lead the offense, despite never having played point guard in her career. 

Williams proved more than capable, finishing fourth in the league in assists per game behind Courtney Vandersloot, Alyssa Thomas and Chelsea Gray, while notching two triple-doubles.

During an appearance in September with her shoe partner, Moolah Kicks, Williams told the Sun-Times that she would love to return to the Sky. The franchise’s hiring of Teresa Weatherspoon as its new coach made the possibility even more appealing.

“I’m thinking about free agency now,” Williams said. “But there are so many different moving pieces, and there’s a ladder to free agency. Like, [Jonquel Jones] is a free agent, is she going back to New York? [Diggins-Smith], there’s so many people that you have to wait and see what they look like.”

Diggins-Smith, a six-time All-Star, will be one of the most highly sought-after free agents. She already has taken to social media to discuss where she might land.

Diggins-Smith posted to X, formerly Twitter, asking fans which teams they thought would be a good fit. After one suggested the Liberty, Diggins-Smith asked, “Would I come off the bench?”

In Chicago, the answer would be absolutely not.

A hypothetical starting five for the Sky would have Diggins-Smith at the point alongside Kahleah Copper and Marina Mabrey or Courtney Williams if the Sky re-sign her. Elizabeth Williams and a healthy Isabelle Harrison would start in the frontcourt.

Giving the rumors legs is Weatherspoon’s familiarity with Diggins-Smith.

“I’ve had a relationship with Skylar since she was a little girl,” Weatherspoon told the Sun-Times. “I’ll just say this: Sky, Skylar.”

The Sky still are searching for a general manager after hiring Weatherspoon this month. When asked what her role will be in constructing the roster, the five-time All-Star said she has been included in every conversation.

Weatherspoon said she hasn’t had any conversations with Diggins-Smith or any players regarding free agency. The intrigue — not solely from the Sky’s new coach, either — is already apparent.

“Big-time player,” Copper told the Sun-Times when asked for her thoughts on the Olympic gold medalist potentially joining the Sky. “I think this is pretty close to home for her, too, right?”

Copper is correct.

Diggins-Smith’s hometown — South Bend, Indiana — is 91 miles from Chicago, further fueling the free-agency fire.

“Skylar would be a great fit,” Copper added. “I think she would help us get another championship.”

Asked if they’d been in touch, Copper smiled and said no.

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