Sydney Taylor’s game-winning three against the Las Vegas Aces was the kind of moment that can trick you into forgetting how rough a season really is.

She dropped 29 points, Chicago clawed back from a 13-point second-half deficit, and the undrafted rookie calmly hit the winner with less than a second left. It was the Sky’s second win in three days, and another reminder that Taylor might be one of the biggest surprises in the entire 2026 rookie class.

And then you look up and see the record: 11–18.

That’s where things snap back to reality. Because as fun as Taylor’s rise has been, she’s not the only bright spot. Kamilla Cardoso is having the best season of her career. Gabriela Jaquez has flashed real potential when she’s been healthy. Rickea Jackson looked like she was on the verge of a breakout before her ACL tear just four games into the year.

There are real players here worth investing in. The problem is the team around them doesn’t really function like one.

Chicago's still outside the playoff picture with 15 games left. The offense has struggled all year, the three-point shooting comes and goes, and the opening-night roster has barely had a chance to be on the court together. It’s all adding up to a third straight losing season, even after an offseason that was supposed to signal the rebuild was over.

Normally, a season like this at least comes with a silver lining: you lose enough games, you get a better draft pick, and you keep building.

But even that safety net isn’t there for Chicago.

Their own 2027 first-round pick can be swapped by Washington. Their 2028 first is already gone to Washington entirely. The rest of those picks in those years belong to Atlanta, a team that’s already winning and looks nothing like a lottery-level squad.

So the Sky are stuck in the worst possible spot: a roster that isn’t good enough to win, and a future they don’t even control to properly rebuild.

That’s about as frustrating as it gets in team building.

Chicago Tried To Skip The Slow Part

The current mess didn’t start with Rickea Jackson’s knee or any one offseason move that went wrong. It’s been building for a while now. Chicago has basically been treating draft picks like chips at a casino table — something to cash in whenever a veteran becomes available or a trade looks like it might speed things up. The idea has always been: we’re close, let’s just skip a few steps.

The problem is, it hasn’t really worked out that way.

Back in February 2025, general manager Jeff Pagliocca sent out the No. 3 pick, a 2027 second-rounder, and the right to swap 2027 firsts to Washington for Ariel Atkins. On paper, it made sense. Atkins was a steady, two-way guard who could defend, shoot, and bring some grown-woman stability next to Reese and Cardoso. Chicago wanted to get better right away, not wait around for teenagers to develop.

But Washington turned that No. 3 pick into Sonia Citron, and she didn’t take long to look like a franchise piece. She made an All-Star team as a rookie, averaged 14.9 points, and basically looked like someone you build around for the next decade. Meanwhile, Atkins gave Chicago 13 points a night on a 10–34 team, then was gone a year later — flipped to Los Angeles in the deal that brought in Jackson.

And to be fair, Jackson could have made all of that worth it. She’s only 25, she was under control, and she looked really good early — 18 points per game in her first four starts before the ACL injury shut everything down. That’s not a bad gamble in a vacuum. Chicago didn’t trade for a washed-up vet who fell off a cliff.

The issue is everything that got attached to that gamble.

The No. 3 pick never came back. The 2027 swap never came back. So in the end, Chicago basically turned Citron, a second-rounder, and control of their own future pick into one season of Atkins… and then flipped that into four games of Jackson.

And look, nobody is blaming Jackson for getting hurt. That part is just awful luck. You can’t plan for that.

But the original cost? That’s still on the front office.

And this wasn’t a one-off thing either. Chicago did something pretty similar with the pick that eventually became No. 2 in the 2026 draft. First, they gave Minnesota swap rights in the deal that helped them move up to get Angel Reese in 2024. Then a year later, they sent Minnesota the actual pick in exchange for the No. 11 selection in 2025.

That pick turned into Hailey Van Lith.

Van Lith struggled as a rookie — 3.5 points per game — and ended up getting waived before the 2026 season so Chicago could bring in Natasha Cloud. Minnesota, meanwhile, used that pick on Olivia Miles at No. 2. She’s now putting up 19.4 points and 5.8 assists for a dominant Lynx team and is basically running away with Rookie of the Year.

And the only reason Chicago even had the No. 5 pick to take Jaquez was because of an older Marina Mabrey trade that left them with a separate pick from Connecticut. The whole chain of moves is so tangled it almost needs a diagram to follow.

But when you zoom out, it’s actually pretty simple.

A 10–34 season turned into Olivia Miles in Minnesota… and Hailey Van Lith getting waived in Chicago.

And honestly, that should’ve been the warning sign.

The Plan Was Fragile Before It Broke

Chicago spent the 2026 offseason acting like a team that was finally ready to turn the corner, like all the pieces were about to click into place and they just needed a couple of right moves to speed things up.

The biggest one, of course, was moving Angel Reese to Atlanta for a package of first-round picks in 2027 and 2028. That deal basically closed the book on a relationship that had been getting more and more tense. Reese had been openly critical of the roster the year before, got suspended for comments the team didn’t love, and by the time April rolled around, it felt like both sides were already halfway out the door. Pagliocca framed it as “roster balance,” but it was pretty clear this was also about hitting reset in a way that still kept future assets in play.

After that, Chicago went into full shuffle mode. They brought in Skylar Diggins, DiJonai Carrington, and Azurá Stevens. They brought Courtney Vandersloot back into the fold, along with Elizabeth Williams and Rachel Banham. They flipped their own 2028 first-round pick for Jacy Sheldon, drafted Jaquez fifth, and later added Natasha Cloud after waiving Van Lith.

On paper, it looked like activity. It looked like urgency. Honestly, it looked like they were trying to fix everything at once. But it didn’t really look like a roster that had a clear identity or even a real direction.

And then you look at how the season actually started, and it gets even more complicated. Chicago opened with three of the five active career assist leaders in the league — Vandersloot, Diggins, and Cloud — all on the same team. That sounds impressive until you remember all three are natural floor generals who want the ball in their hands. Add in the fact that Diggins is 36, Cloud is 34, and Vandersloot is 37 coming off an ACL tear that limited her to just seven games the year before, and suddenly it feels less like a luxury and more like a logjam.

The injury situation just made everything worse. Carrington came in already dealing with a foot issue, then needed another procedure and didn’t debut until July 30 after missing 27 games. Stevens was managing a knee problem from the start. Vandersloot didn’t even return until late June and was on a minutes restriction. Jaquez missed time with a knee injury. And then Jackson’s ACL tear basically took away the one player who could consistently create her own shot and carry the scoring load night to night.

At a certain point, it’s fair to say injuries wrecked any real chance of seeing what this team was supposed to be. That matters. It really does.

But it also doesn’t completely excuse how fragile the whole thing was from the start.

Chicago brought in multiple players who had injury concerns, stacked veteran point guards on top of each other, and ended up thin in the frontcourt after moving on from the league’s best rebounder. The whole structure depended on a lot of things breaking right at the same time — Jackson needing to be a primary scorer, Cardoso taking a leap, Jaquez contributing right away, and a long list of veterans staying healthy or quickly returning to form.

That’s a lot to ask in the best of circumstances. In reality, almost none of it held.

Jackson played just four games. Carrington missed months. Jaquez was in and out. Vandersloot came back slowly. Stevens missed time early and has recently been away for personal reasons. Diggins has dealt with her own injuries and at times hasn’t had a clear, consistent role.

Chicago actually started 3–1, which briefly made everything feel like it might work. Since Jackson went down, though, they’ve gone 8–17, and the season has slowly drifted into something much more familiar.

There is still talent here. Cardoso is putting together a strong year — over 14 points, eight rebounds, and real playmaking. Stevens has been solid when she’s on the floor. Diggins can still score and run an offense in stretches. Vandersloot, even at this stage of her career, can steady things when she’s healthy.

But the problem is the same one that’s been hanging over this roster all year: it doesn’t really fit together in a way that makes sense. It’s more a collection of names than a functioning system.

Even the Jacy Sheldon trade looks harder to justify as the losses pile up. She’s shown some shooting and defensive upside, but Chicago gave up their own 2028 first-round pick for a guard who is currently putting up 7 points and 2 assists. Maybe she develops into a steady starter. She almost has to, just for the price tag to feel remotely reasonable.

The Sky Still Have Something Worth Saving

Taylor’s emergence has honestly been the one thing that’s made this season in Chicago feel like it’s had any real upside at all.

She came into the league undrafted after bouncing between UMass and Louisville, started the year buried on the bench, and now she’s basically the Sky’s go-to scorer. She’s putting up 18.4 points a night, hitting nearly 40% from three, and in just 16 starts she’s already had five games with 25 or more points. That game-winner against Las Vegas wasn’t just a highlight — it kind of summed up how quickly she’s gone from afterthought to centerpiece.

You’ve got her, Cardoso continuing to grow into a legit interior force, Jackson when she’s healthy looking like a real scoring option, and Jaquez showing flashes that make you think there’s something there long-term. Add in Carrington, who at 28 still brings the kind of defensive edge and toughness this roster desperately needs, and suddenly it’s not all doom and gloom.

Even the Atlanta picks they’re sitting on still matter, even if neither one ends up being a top-tier lottery swing. There’s a version of this where it all actually comes together.

But getting there takes something Chicago hasn’t really shown much of lately: patience.

The front office has to stop acting like every half-built roster just needs one more big swing to magically turn into a contender. At some point, you have to let the young players actually grow into something instead of constantly reshuffling the deck.

And bigger picture, ownership has to seriously think about whether Pagliocca is the right person to clean up a situation he’s been deeply involved in creating.

The Sky aren’t hopeless. Teams that are truly hopeless don’t have Cardoso, don’t have Jackson, and don’t stumble into one of the most productive rookies in the league. This isn’t a completely empty cupboard.

But it is a messy one.

All stats courtesy of WNBA.com.

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