The Chicago Sky are a disaster of their own making

CHICAGO — Another Chicago Sky season was lowered into the grave on a Sunday night at Wintrust Arena. The official cause of death was a flurry of third quarter three-pointers by Indiana Fever stars Caitlin Clark and Kelsey Mitchell that turned a close game into a blowout and ripped the slim playoff hopes out of Chicago’s hands. In reality, the Sky’s mathematical elimination was a long time coming, with the feel of a slow-motion train wreck that anyone could have spotted but no one could have prevented. It was the type of inevitable disaster that has defined this franchise ever since its magical 2021 championship run, and at this point, it’s starting to feel like there’s no way out.

This is the third straight season the Sky have missed the playoffs. Injuries will be a convenient excuse, and there’s some truth to it. Chicago started the year 3-1 before star forward Rickea Jackson tore her ACL. That injury began a run of 11 losses in 12 games that effectively ended the Sky’s season on contact. It’s easy to fantasize about how this season might have turned out differently had Jackson stayed healthy, but there were always going to be too many leaks in this proverbial boat for smooth sailing. Under general manager Jeff Pagliocca, fantasy is the only thing Sky fans have to latch onto.

This Sky season was destined to be forgettable when the team traded Angel Reese to the Atlanta Dream for two first-round picks before training camp opened. Reese had developed into a homegrown star in her two seasons with the organization, but she wore out her welcome by refusing to accept the mediocrity that surrounded her.

“I’m not settling for the same s— we did this year,” Reese told the Tribune at the end of last season. Her comments feel clairvoyant with a year of hindsight, especially when she put an even finer point on it by calling for an upgrade at lead guard.

“We can’t rely on Courtney to come back at the age that she’s at,” Reese said.

Reese may as well have booked her ticket out of town when she uttered Courtney Vandersloot’s name, even if she was obviously right. Vandersloot isn’t just a Sky legend, she’s also closely aligned with Pagliocca, the lead executive who got his start as her personal trainer. Reese was suspended a game for her comments, and in that moment Chicago seemingly had a power struggle on its hands between a 24-year-old rising star and a 37-year-old coming off a torn ACL.

Any sensible franchise would have aligned with Reese, but nothing the Sky do is sensible. In many ways, it feels like Chicago has been catering to Vandersloot since it brought her back following a short stint with the New York Liberty that ended with the loss in the 2023 WNBA Finals. Pagliocca has consistently traded away future draft picks to try to build a “competitive” team around Vandersloot in her golden years, but all he’s ended up doing was mortgaging the team’s future for disappointing seasons that never had any real chance to pay off in worthwhile fashion.

A few years from now, you might be able to build an All-WNBA team with the draft picks Pagliocca has traded away in an attempt to please his old client Vandersloot. The results are already horrifying, and there’s surely more pain coming.

Back in 2024, Pagliocca traded up one spot from No. 8 to No. 7 to draft Reese. The move cost him a 2026 first-round pick swap to Minnesota when it’s likely the Lynx wouldn’t have drafted Reese in the first place. The Sky missed the playoffs in both years that Angel was on the team, and that draft pick ended up being No. 2 overall. Minnesota drafted Olivia Miles, who might be the best rookie point guard professional basketball has seen since Magic Johnson.

Miles will probably finish second in MVP voting this year. It feels like she’s already a better player than Caitlin Clark, and she should have been the face for the Sky for the next decade. The trade up for Reese was reckless at the time, and will now go down as an all-time WNBA blunder.

That’s just the start of it. Go back a year earlier, and Pagliocca traded the No. 3 pick in the 2025 draft for veteran Ariel Atkins. This was a senseless trade at the time, because the Sky needed to be stockpiling young talent to build for the future, not searching for a shortcut to a low-end playoff spot. The Washington Mystics jumped at the trade, selected Notre Dame wing Sonia Citron, and watched her turn into a WNBA All-Star in her first two seasons.

A backcourt with Miles and Citron would have been box office, and complemented each other perfectly. The Sky gave that away to go 38-84 over the last three seasons.

Pagliocca simply has to be fired when this season is over. If he retains his job, it’s more proof that the Sky are not a serious franchise. Unfortunately for Chicago, a new lead executive will be handcuffed from the moment they accept the job, because Pagliocca has already traded away the team’s future 2027 and 2028 draft picks, too.

The 2027 first-round pick was sent to Washington as part of the Atkins trade. Right now, that pick would have the third-best chance to win the lottery, with USC superstar JuJu Watkins as the likely top pick. The 2028 first-round pick was traded for Jacy Sheldon before the start of this season. That deal has a chance to be the most painful of all with generational UConn big Sarah Strong set to headline the class.

Trading an unprotected first rounder in Strong’s draft class for a player of Sheldon’s caliber shows just how far Pagliocca is in over his head. It’s not that Sheldon is terrible — she’s a solid 3-and-D guard — but she’s exactly the type of low-upside swing that no franchise should be selling out its future for. Sheldon is averaging 6.4 points per game this season. She is an agonizingly low-usage guard who has never had a usage rate greater than 14.1% in the WNBA.

The Sky need a star. A player with a 14% usage rate has zero chance of ever becoming a star. It’s a premium example of the Sky going all-out to chase middling success that they couldn’t even accomplish.

There are more blunders from there. Hailey Van Lith was always a poor use of a first round pick, and she only lasted one season before the team released her. The team’s other 2025 first-round pick Ajša Sivka still hasn’t come to the WNBA, and seemingly regressed last year overseas. Now she’s slated to play college ball this season at Kentucky.

How will history remember Pagliocca’s selection of Gabriela Jaquez at No. 5 overall this year? Jaquez felt like a reach at the time, especially when her UCLA teammate Kiki Rice was sitting there for the taking. Jaquez has had her moments, but she’s another low-usage connective wing who is unlikely to turn into a star. As the Fever ended the Sky’s playoff chances on Sunday night, Jaquez was a healthy scratch. I asked Sky head coach Tyler Marsh why Jaquez wasn’t part of his 10-person rotation, and if the team would start to prioritize development more now that they’re eliminated from playoff contention. He mostly stumbled his way through a non-answer.

Rice has been killing it lately in Toronto after getting healthy from an early season injury. She looks like she could be the engine of a team one day. If they drafted Rice, the Sky could have locked down their point guard of the future. Maybe Pagliocca still thinks that’s Vandersloot’s role.

Regardless of how you project Jaquez, she should have been given a longer leash this year to develop. The Sky sat her to give heavy minutes to the likes of Natasha Cloud and Rachel Banham, who are in their mid-30s. This team was never going to be good once Jackson got hurt, and that should have shifted their priorities to developing younger players on the roster. Maybe Jaquez has more upside than her rookie numbers show, but she never really got a chance to play through her mistakes this year, which is another ultimate failure in a lost season.

The Sky aren’t just a bad franchise because they’ve empowered a hopeless GM who was always unqualified for the job. All the issues start with ownership, and it’s the biggest reason the Sky are a laughingstock within WNBA circles.

The Sky lost a superstar in part because they didn’t have their own training facility back in 2014 when Sylvia Fowles pushed her way to Minnesota. Chicago still doesn’t have its own training facility after its new Bedford Park complex — located nearly 14 miles away from its home gym at Wintrust Arena — was delayed again this year.

The training facility fiasco has been a black eye in every way. This past offseason, Bec Allen, who spent one season with the Sky last year, went on a podcast and spoke about Chicago using a rec center for practices.

“I had a random lady getting changed next to me,” Allen said. “Hey, Wendy!” When asked to describe her experience in Chicago in one word, Allen said “Miserable.”

A training facility isn’t the only thing the Sky are lacking. The organization doesn’t have a dedicated analytics team in the front office, and Pagliocca has stated the team has no plans to hire one.

The one thing the Sky have done right this year is identify Sydney Taylor as an undrafted free agent. Taylor has been spectacular, giving Chicago a mix of pull-up shooting and rim pressure that only the league’s best scorers possess. She feels like this year’s second-best rookie behind Miles, and she should be the team’s long-term shooting guard. The Sky also found a solid two-way contributor with Aicha Coulibaly, who Pagliocca selected in the second round of 2025 and signed to a developmental deal this season. Coulibaly is a versatile defensive forward with some scoring juice. Taylor is a walking bucket. Add in Jaquez, and there’s a little hope for the future.

It’s telling that Kamilla Cardoso hasn’t been mentioned until this point. Pagliocca took her with the No. 3 overall pick in 2024, and it’s still hard to tell if she can be the franchise’s long-term starting center. Cardoso’s motor runs hot and cold, she lacks mobility and a jump shot, and she’s always in foul trouble. The Sky will have a big decision on her as she enters the final year of her rookie deal next season.

Even the optimist’s case for the Sky isn’t very convincing, mostly because this franchise has been mismanaged at every opportunity since former head coach/GM James Wade left for the Toronto Raptors. The way forward is firing Pagliocca and letting Vandersloot gracefully retire or leave as a free agent in the offseason, but it’s going to be nearly impossible to build back up in the short term without control of their next two first-round picks.

Chicago is too good of a basketball town for the Sky to be so mismanaged. The city has multiple bars dedicated to women’s sports, and it threw a fantastic All-Star Weekend this year that brought 20K fans to the United Center this July. Of course, the Sky didn’t have a single player at the All-Star Game while Reese was there representing the Dream as she enjoys the best year of her career. Those two first-round picks the Sky got back for Reese are going to be very late ones.

Pagliocca never had the credentials to land a GM job as a former skill trainer. Vandersloot has now been given more grace from the Sky than the Bulls ever gave to Michael Jordan. The only payoff for a bad season is a high draft pick, and the Sky have already traded those away well into the future. Meanwhile, Pagliocca is only making headlines for welcoming another former client, Enes Kanter, to Sunday’s game, where he served as a huge distraction before being ejected for getting into it with Cloud.

The WNBA is zooming into the future, but the Sky are getting left behind. It’s a catastrophe solely of their own making. At this point, the hole is so deep that it’s going to continue to engulf them for years to come.