The Chicago Sky enter the 2026 WNBA season with a very different look from the team that ended 2025. Gone is Angel Reese, who was traded to the Atlanta Dream, while three — or maybe even four — new starters will take the floor. Could this be the year that the Sky finally get back to their previous levels of success?

We’ll see, but there are still plenty of questions about where this team is at right now. Some questionable trades have emptied the cabinet of future first-round picks, so Chicago is motivated to win now, but is this a win-now roster?

Projected Chicago Sky depth chart

Here’s my best guess at a 12-player rotation for the Sky. Among players I didn’t mention, Latasha Lattimore making the roster to provide forward depth could happen, and it’s possible that when other roster cutdowns happen that the team could look for a better backup guard than Hailey Van Lith, someone who can play more of the two.

Now, let’s look at some of the major questions about this roster.

Who starts beside Skylar Diggins in the backcourt?

Landing Skylar Diggins this offseason was huge. Sure, the seven-time All-Star is 35 years old, but she still averaged 15.5 points and 6.0 assists per game for the Storm last season while posting her best 3-point field goal percentage since 2021. She still has it.

The question is who the Sky will pair her with in the backcourt. There’s franchise legend Courtney Vandersloot, one of the best point guards in WNBA history, but age has caught up to Vandersloot in a way it hasn’t with Diggins. She played just seven games last season and while she averaged 10.6 points and 5.3 assists, she also had one of the lowest field goal percentages of her career.

On the plus side, though, is that a Vandersloot-Diggins backcourt would be great from a passing perspective, and it lets you use Diggins more off the ball, expanding the range of what you can do.

The other option is Jacy Sheldon, who the team just traded for. Sheldon is a far better shooter at this point in her career than Vandersloot, so putting her beside Diggins — with Diggins as the primary ball-handler — sets Sheldon up to be a lethal catch-and-shoot player, though you’re sacrificing some playmaking in this scenario.

For my money, I think you try Vandersloot in the starting five early on, but you do so with the plan to make a quick change if her lack of shooting becomes an issue.

How long will the Sky be without DiJonai Carringtton?

The Sky have Diggins at the two and new additional Rickea Jackson at the three, but the best option to back both players up, DiJonai Carrington, is currently sidelined with a foot injury. The latest update did not give a timetable for her return.

So, uhh…what does that mean for the Sky? If Carrington isn’t out too deep into the 2026 season, the team will probably be fine, but Carrington’s extended absence leaves you with issues, especially at the three. Do you wind up relying more than you want to on Rachel Banham? Does rookie Gabriela Jaquez get thrown immediately into the fire? Does Jackson just have to play, like, 38 minutes per night or something?

Carrington might have flaws to her game, but her defensive abilities make her a great fit off the Sky bench. Until she’s back, the team will need to cobble together its wing depth in a way that could cost it a few games.

Is there enough frontcourt depth?

I highlighted Lattimore as someone who could theoretically play her way on to this roster, and a big reason why is that there’s not a ton of depth in the frontcourt, so if it comes down to a numbers game, Lattimore could sneak on over Van Lith.

As long as they both stay healthy, the center rotation of Kamilla Cardoso and Elizabeth Williams is probably fine. Has Williams lost a step at this point in her career? I’d argue yes, but the Sky just need her to give them 10-15 minutes per game, and that’s something she should be able to do. If Cardoso can stay out of foul trouble and play 25 minutes per night, you can survive there, especially with Azura Stevens able to slide to the five in smaller lineups.

But the other frontcourt spots are way more iffy. I mentioned the small forward depth concern above so I won’t rehash that, but the situation at the four feels rough as well. Stevens is a great option in the starting unit, a player who can stretch the floor on offense and protect the rim on defense. Behind her, though, is Maddy Westbeld and…that’s all? Westbeld has upside, but also averaged just 4.1 points and 2.4 rebounds as a rookie. She can shoot the ball well so she’s fun as a backup stretch four, but the team would be in trouble if Stevens went down, and that could be very bad news for Chicago’s hopes of making the playoffs.

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