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The Long-Awaited Blowup Between Skylar Diggins And The Sky Has Finally Arrived

Skylar Diggins #4 of the Chicago Sky warms up prior to the game against the Portland Fire at Wintrust Arena on June 26, 2026 in Chicago, Illinois
Daniel Bartel/Getty Images

Skylar Diggins, to her credit, isn't one to trade in the classic cryptic fare of her fellow disgruntled athletes. What she writes on social media requires no close reading or careful analysis. There's no Crazy how people switch up on you or TIME WILL TELL with an enigmatic emoji. The Instagram story she posted on Monday was perfectly straightforward: "Now I'm coming off the bench?????? 👍🏽 Cool."

Two questions sprang to mind when Diggins signed a two-year, $1.8 million deal with the Chicago Sky this past offseason. How would she coexist with veteran point guard Courtney Vandersloot, who was recovering from an ACL injury but was expected to rejoin the team midseason? (Later, when point guard Natasha Cloud signed with the Sky in free agency, that question expanded.) Also, why was Skylar Diggins, who always speaks up when she feels she's not being treated right, choosing a team famous for not treating players right?

At an introductory press conference the team held for its new free-agent signings in early April, those questions came up. For her part, Diggins said she'd chosen Chicago in part because it presented her the opportunity to "learn from players I always looked up to, like Courtney Vandersloot." She also said she'd been talking to players around the league during the offseason and trusted her own discernment. As Sky head coach Tyler Marsh put it then, "Players are aware of the negative things that get said … Skylar's been around this league a long time to know the fake from the real."

It felt a little much to dismiss the franchise's documented cheapness and its decade-long star exodus as "fake," but whatever; if Diggins and the Sky were happy together, they were happy together. They even moved on from what seemed like a possible rupture in early June. Asked—or almost asked—a question about the sputtering offense after a road loss to Toronto, Diggins interjected to tell a reporter, "That's a Tyler question. Ask Tyler." But things seemed to cool down after that.

Now they are no longer happy together. Vandersloot made her season debut on June 26 against the Portland Fire, and came off the bench for three games before Marsh moved her into the starting lineup for Tuesday's Sky-Mercury game in Phoenix. Diggins evidently found out the morning before practice on Monday. In a front-facing video she shared to her story after her initial reaction, she said, "And the crazy part about it all is that I've been so quiet. I've been so good and quiet. I've been so good and quiet."

The basketball case for changing up the Sky's starting group isn't totally outlandish: The offense has looked quite good when Vandersloot runs it. She recorded seven assists in just 14 minutes in that first game back against Portland, and followed it up with eight assists in 16 minutes in a close loss to Vegas a couple days later. I was skeptical that she could do much with this Sky team—and their recent success might be an artifact of a softer schedule without frontcourt defense to worry about (the Portland Fire, the Mercury without Natasha Mack, and the Aces without A'ja Wilson)—but no question they've been a better team for her presence. Diggins is averaging 4.9 assists per game, and her scoring isn't too far below her career numbers, but she's been less efficient, particularly as a finisher at the rim. 

This was always the challenge of rostering three ball-dominant veteran point guards who could each reasonably expect to start for a WNBA team this year. (A team, not necessarily a good one.) Marsh and general manager Jeff Pagliocca knew someone was going to be left unhappy. I imagined Diggins playing off the ball next to Vandersloot, while Cloud came off the bench, as she already has this season, but Marsh saw things differently. You can understand why Diggins might be offended: In Tuesday's game against Phoenix, breakout undrafted rookie guard Sydney Taylor got another start, and Cloud was also swapped into the starting lineup for rookie Gabriela Jaquez, so that the Sky were actually starting three non-Diggins guards. 

Diggins's problems with Marsh do seem to go beyond the benching; where she was "so quiet" before, now she may feel a little more licensed to name them. Take her interview with the Chicago Sun-Times on Tuesday:

Asked why the Sky have struggled to close games, Diggins said she wanted to choose her words carefully to avoid being a jerk.

"We don't discuss late game very often," she said. "I don't think we have a set/reset play to run. We've been in that situation a lot of times. I would love to hear what [Marsh's] late-game strategy is as far as what exactly we’ve been doing."

Aside from a pair of games fresh off an injury in 2016, Diggins had not come off the bench since her rookie year in 2013, and she does not seem inclined to start. "I've been sacrificing my body for this team," she told the Sun-Times after Monday's practice, sharing that she'd had knee surgery in the offseason. "Maybe it's time to take a step back and see what's going on to see if I need to continue to make those sacrifices without having the proper resources to play at an elite level."

Sure enough, Diggins was a late scratch from Tuesday's game, listed out with a knee injury despite not having been on the injury report before. Vandersloot, still on a minutes restriction, had a quieter night, but the Sky won, 77-66. 

You'll note Diggins's earlier mention of not having "the proper resources to play at an elite level." She told the Sun-Times that she'd expected the Sky's new practice facility to be done by now, and implied that she's struggled "emotionally" under the circumstances. "I was thinking we were going to be in a practice facility, and other things that were told to me. And that's not been the case. There's been things outside of people's control that I understand, too, a lot of moving parts. Lots of places I've been were in that process as well, so I get it. But it's hard to perform at a certain level without those [resources]."

In February, the organization said the facility was due to be "operational by late spring," then later said it would be ready at some point this season, but there is no official opening date, and it won't host any events when the All-Star Game happens in Chicago in less than three weeks. Diggins may be well-traveled, but here was some new wisdom for her: Be careful trusting the Chicago Sky.

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