Another Chicago Sky season has gone up in flames. After a strange offseason that saw the team trade away Angel Reese but then add Rickea Jackson, Azura Stevens and Skylar Diggins, there was some hope for a playoff run for the team. Instead, it's a third consecutive season missing the postseason. The team has felt adrift since the end of the James Wade era, and it's not really clear what's next from here.
What is clear is that the team can't go into 2027 with this same roster. These three players feel especially done in Chicago following the team's 2026 struggles.
Skylar Diggins
I mean...you have to trade Skylar Diggins this offseason. There's no getting around it. The decision to add her this season did nothing to improve the Sky and the tension that existed between her and the team for much of the year feels like something that can't really be salvaged.
And this isn't even about the off-court stuff, specifically the rumors that Diggins was going to be moved to the bench, which never happened because she re-aggravated her knee and hasn't played since. The on-court fit with Diggins was off as well. The Sky's net rating is -5.7 points worse with Diggins on the floor, the second-worst net on/off on the roster. The defense was noticeably worse when she played.
Could the two sides fix things up? Sure, maybe. But the issue is that the Sky likely won't be much better in 2027 anyway, so why not try to move Diggins for any kind of asset when you have the chance? Sure, you'd be selling low on her, but for a team that's consistently given up assets while chasing non-existent wins, it'd be nice to get an asset back this time.
Natasha Cloud
Even if you move on from Diggins, the Sky still have a guard problem, as the team has Natasha Cloud, Courtney Vandersloot and Jacy Sheldon. The easiest way to clear that up? Just let Cloud walk in free agency.
Vandersloot and Sheldon both have protected deals next season. Vandersloot could theoretically retire, but she's played well enough that she deserves an actual retirement tour in 2027. Sheldon hasn't played enough this year, but the Sky gave up a first-round pick for her, so holding on to her and seeing if she can perform well in a larger role is the right call.
Cloud is playing well, with her 49 percent shooting mark being the best of her career, but she's also 34 years old and barely found a home for the 2026 season. At this point, Cloud should take this chance, with her production at one of its highest points, to pursue a chance to play for a contender. It might be her final chance.
DiJonai Carrington
DiJonai Carrington is a free agent this offseason and considering the current state of this roster, I can't really imagine her sticking around, especially with her averaging her fewest minutes since her rookie season.
Shooting has never really been Carrington's strong suit, though there have been occasional flashes of it, like when she shot 45.5 percent from deep in her 11 games with the Minnesota Lynx last season. She's the kind of player who plays at her best when the team around her is playing at her best. There's no reason to think Chicago is that place, right?
I mean, the Sky aren't the worst team in the world, but the ceiling is still super low, something like "sneaks into the No. 8 seed if Rickea Jackson is healthy then loses in the first round," and that's not the likeliest outcome for the team. This is a team that needs to rebuild — and that also doesn't have its own first-round pick next year to help with that — and Carrington is a player who doesn't need to be stuck in that situation.
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