Chicago Sky’s Disheartening Season Comes to an End

CHICAGO — The Chicago Sky’s latest season came to a grim conclusion on a Sunday night at Wintrust Arena. The decisive moment was a barrage of three-pointers during the third quarter by Indiana Fever stars Caitlin Clark and Kelsey Mitchell, which turned a tight game into a lopsided defeat, effectively crushing the Sky’s faint playoff ambitions. Yet, that mathematical elimination felt oddly anticipated, like a slow-motion train wreck that observers couldn’t avert. This unfortunate turn has become a signature of the franchise since their glory days in 2021, and it increasingly appears that a way forward remains elusive.

This marks the third consecutive season the Sky has failed to make the playoffs. Injuries will serve as a convenient explanation, and there’s some validity to that. The team began the season with a record of 3-1 before star forward Rickea Jackson suffered a torn ACL. That injury initiated a dismal stretch of eleven losses in twelve games, which pretty much sealed the fate of the Sky’s season. It’s tempting to speculate how things might have unfolded differently had Jackson been healthy, but there were always too many holes in this figurative boat to ensure smooth sailing. Under general manager Jeff Pagliocca, all fans of the Sky have left is a bit of fantasy to cling to.

This season became forgettable the moment the team decided to trade Angel Reese to the Atlanta Dream for two first-round picks before training camp even started. Reese, who had grown into a local star during her two years with the team, had worn out her welcome—perhaps simply unwilling to accept the mediocrity that surrounded her.

“I’m not settling for the same s— we did this year,” Reese stated at the end of last season. Looking back, those comments seem almost prophetic, especially as she called for an improvement at the lead guard position.

“We can’t rely on Courtney to come back at the age that she’s at,” Reese remarked, which was a bold statement. Mentioning Courtney Vandersloot, I mean, it felt like a declaration of intent, even if Reese had a point. Vandersloot is not only a beloved figure in Sky history but also closely connected to Pagliocca, who began his career as her personal trainer. For those comments, Reese faced a one-game suspension, highlighting a power struggle between a promising 24-year-old and a veteran 37-year-old recovering from an ACL injury.

Sensible franchises would have sided with Reese, but the Sky, it seems, operate differently. There’s a sense that Chicago has catered to Vandersloot since her return from a brief stint with the New York Liberty, which ended in a loss at the 2023 WNBA Finals. Pagliocca has consistently sacrificed future draft picks in a misguided attempt to build a “competitive” team around Vandersloot during her later years, effectively trading away the team’s future for a series of disappointing seasons that never really had a chance to yield meaningful results.

In a few years, one might put together an All-WNBA team from the draft picks Pagliocca has forfeited in his quest to appease Vandersloot. It’s alarming to consider the depths of this mismanagement, and it seems like more hardships lie ahead.

Back in 2024, Pagliocca traded up from No. 8 to No. 7 to select Reese, which cost him a swap of 2026 first-round picks with Minnesota, a team likely not to choose Reese at all. The Sky missed the playoffs in both seasons Reese played on the team, with that eventual draft pick turning out to be the No. 2 overall. Minnesota chose Olivia Miles, a rookie point guard who may be the best to enter the league since Magic Johnson.

It feels like Miles could secure the second spot in MVP voting this year. At this point, she seems like she would have made a perfect face for the Sky for the next decade. Looking back, that trade-up for Reese appears reckless and will likely be recognized as one of the biggest blunders in WNBA history.

This is just a fraction of the overall issue. A year before that, Pagliocca exchanged the No. 3 pick in the 2025 draft for veteran Ariel Atkins. At that moment, this trade seemed illogical, as the Sky should have been focused on accumulating young talent for the future instead of seeking a shortcut to merely scrape into the playoffs. The Washington Mystics seized the opportunity, picked Notre Dame’s Sonia Citron, and she quickly blossomed into a WNBA All-Star in her first two seasons.

Just imagine a backcourt featuring Miles and Citron; it could have been electric and perfectly complementary. Instead, the Sky gave that chance away, resulting in a disappointing 38-84 record over the last three seasons.

There’s really no way to avoid the conclusion that Pagliocca needs to be let go once the season wraps up. If he retains his position, it will only further illustrate that the Sky aren’t regarded as a serious franchise. Unfortunately for Chicago, any new lead executive would be stepping into a challenging situation from the start; Pagliocca has already traded away draft picks for 2027 and 2028, limiting their options.

The 2027 first-round pick went to Washington in connection with the Atkins trade. Presently, that pick has the third-best chance in the lottery, with USC superstar JuJu Watkins likely to be the top pick. Likewise, the 2028 first-rounder was exchanged for Jacy Sheldon earlier this season, and that deal could sting the most given that generational talent Sarah Strong is set to lead the upcoming draft class.

Exchanging an unprotected first-round pick in Strong’s draft for a player like Sheldon illustrates just how much trouble Pagliocca is in. To be clear, Sheldon isn’t underperforming—she’s a decent 3-and-D guard—but she’s precisely the kind of low-risk player no franchise should be compromising its future for. Currently, she’s averaging about 6.4 points per game with a usage rate that has never exceeded 14.1% in the WNBA.

The Sky are in desperate need of a star player. A guard with a mere 14% usage rate isn’t likely to ever reach that status. This situation stands as a prime example of the Sky going all-in for mediocre success that they didn’t even manage to achieve.

The list of miscalculations doesn’t end there. Drafting Hailey Van Lith as a first-round pick proved to be a poor choice, especially since she lasted just one season before being released. The other 2025 first-round pick, Ajša Sivka, has yet to join the WNBA and reportedly regressed while playing overseas, ultimately deciding to play college basketball at Kentucky this season.

What will history say about Pagliocca’s choice of Gabriela Jaquez at No. 5 overall this year? Jaquez felt like a reach when selected, particularly with her UCLA teammate Kiki Rice available. She has had some bright moments, yet she remains another player who lacks the high usage and scoring potential needed to evolve into a star. During the game that eliminated the Sky from playoff contention, Jaquez was a healthy scratch. When I asked Sky head coach Tyler Marsh why she didn’t make the ten-person rotation, his response was vague and unconvincing.

Meanwhile, Rice has been putting on a show in Toronto after recovering from an early-season injury, seeming to be a player who could energize a team one day. Had they chosen Rice, the Sky might have secured their point guard of the future. Maybe Pagliocca still envisions that role for Vandersloot.

No matter how you view Jaquez’s potential, she should have had more opportunities this year to develop. The team opted to prioritize minutes for veteran players like Natasha Cloud and Rachel Banham—neither of whom are in their prime. With Jackson’s injury, it was clear this team wasn’t ready to compete, and the focus should have shifted to nurturing younger talent on the roster. It’s possible Jaquez has more upside than her rookie numbers indicate, but she never got the chance to work through her growing pains this season, which is a further disappointment in a lost year.

It’s not just that the Sky suffer from a poorly qualified GM; the entirety of their issues trace back to ownership, which significantly contributes to their reputation as a laughingstock within WNBA circles.

The Sky lost a superstar team member largely due to their lack of a training facility back in 2014 when Sylvia Fowles sought to leave for Minnesota. Even now, Chicago still doesn’t have its own facility, as the new complex in Bedford Park—almost 14 miles from Wintrust Arena—has experienced further delays this year.

This ongoing training facility saga has been a significant embarrassment. Last offseason, Bec Allen, who had one uninspiring season with the Sky, shared on a podcast about practices being held at a recreation center.

“I had a random lady getting changed next to me,” Allen explained. “Hey, Wendy!” When asked for a single word to describe her experience in Chicago, Allen simply replied, “Miserable.”

The training facility isn’t the only gap in the organization. The Sky also lack a dedicated analytics team in their front office, and Pagliocca has made it clear there are no plans to rectify this.

On a brighter note, the Sky did successfully identify Sydney Taylor as an undrafted free agent this year. Taylor has shone, delivering a combination of pull-up shooting and the ability to attack the basket that rivals the league’s top scorers. She seems to be the second-best rookie this season, second only to Miles, and could be positioned as the long-term shooting guard. Additionally, Aicha Coulibaly, whom Pagliocca selected in the second round of 2025, has emerged as a solid contributor and is showing promise on both ends of the floor. With Taylor and a developing future in Jaquez, there’s a smidgeon of hope.

It’s worth noting that Kamilla Cardoso hadn’t been discussed until now. Pagliocca selected her with the No. 3 overall pick in 2024, but it’s still unclear if she can be the long-term starting center for the franchise. Cardoso shows a fluctuating effort level, has mobility issues, lacks a jump shot, and often finds herself in foul trouble. The Sky are in for a tough decision as she enters the final year of her rookie contract next season.

Even the most optimistic view of the Sky seems unconvincing, primarily due to the constant mismanagement since former head coach/GM James Wade left for the Toronto Raptors. The way forward appears to be terminating Pagliocca and allowing Vandersloot to retire gracefully or leave as a free agent during the offseason. However, rebuilding will likely be very difficult without the control of the next couple of first-round picks.

Chicago is too passionate about basketball for the Sky to remain in such disarray. The city boasts numerous bars that celebrate women’s sports and successfully hosted a fantastic All-Star Weekend this year, drawing around 20,000 fans to the United Center. Notably, the Sky didn’t send any players to the All-Star Game while Reese was representing the Dream—having a stellar season. Those two first-round picks obtained from the Reese trade are likely to be late selections.

Pagliocca was never equipped with the credentials for a GM role as merely a skill trainer. At this point, the grace extended to Vandersloot from the Sky dwarfs anything the Bulls ever offered to Michael Jordan. The sole benefit of a rough season would have been a high draft pick, yet the Sky have already squandered future picks. Meanwhile, Pagliocca is making headlines for welcoming another former client, Enes Kanter, to a recent game, where he ended up being a distraction and was ejected after an altercation with Cloud.

The WNBA is racing into the future, while the Sky seem to be stuck in place. It’s a catastrophe of their own doing, and at this point, it feels like the hole they’ve dug will continue to entrap them for years ahead.