Based on the festive atmosphere at the Wintrust Arena on August 18, you wouldn’t have guessed that the Chicago Sky were heading into their game against the New York Liberty with a 13-22 record, and near the cellar in the league’s Eastern Conference, behind the Atlanta Dream, Indiana Fever, Liberty, and Washington Mystics.
The Sky will miss the playoffs for the third year in a row, and this year, they’ve failed to send a player to the All-Star Game for the first time in their history, despite hosting the matchup and events in July. Still, the size of the near three-quarters capacity crowd was a sight difficult to imagine just a few years ago, especially for a Tuesday evening, and happy chatter emerged from packed lines into the arena as tipoff approached.
The Sky’s 93-86 victory over the Liberty, firmly in the hunt for a follow-up to their 2024 WNBA title, was cathartic for the crowd witnessing a tough season. The Sky held the lead for most of the game, powered by the performance of veteran guard Natasha Cloud, who electrified the crowd with a career-best 35 points.
The game’s energy was no doubt elevated by its platforming of the team’s annual Latina Empowerment Night. Pop-up shops and info booths lined the 100-level concourse, many brimming with consistent activity throughout the evening. Employees of Pásele Señito, a Mexican artisania store located at 1648 West 18th Street in Pilsen, complemented the arena’s usual selection of basketball-themed knickknacks with a lively spread of Mexican pop-culture art and jewelry.
Across the arena, children’s author Nina D. Sanchez raised money and awareness for her children’s book, Somos / We Are, and the ¡Viva! Los Libros bilingual children’s literacy project.
Running a booth for Azul, a family-owned crafts workshop based in the Bridgeport Arts Center on 35th and Racine, Amber Rosales spoke with pride of “bringing Latino culture through jewelry and accessories into spaces” where they aren’t typically found.
And lately, the Sky have saved their best for the home fans. After losing six of their first seven games at Wintrust this season, the win against the Liberty made for eight in their subsequent 11 tries. A few days later, a dramatic last-minute comeback against the Golden State Valkyries made it nine wins out of 12. Of late, their play has been slightly better than their overall record indicates, as they’re now 11-10 over their last two months of play after an abysmal 4-12 start.
For many fans, it’s certainly too little and too late. The Sky’s loss to the Indiana Fever on Sunday, August 23, quashed their home winning streak and guaranteed a fourth straight losing season. This is the franchise’s longest stretch of subpar play since their inaugural 2006 campaign; it took them seven years to earn a .500 record.
As it was often the case this season, on-court play was overshadowed by off-court events. This time, Cloud—known for her outspokenness and her advocacy of trans athletes—got into a shouting match with former NBA player Enes Kanter Freedom, an anti-trans activist. Team security eventually removed Kanter Freedom and escorted him from the arena.
The loss was not surprising, and some fans attempted to take it—and accompanying distractions—in stride. But as good as vibes have been at recent home games, lifelong South Sider Bethany Pickens, 66, isn’t fooled. When asked how she was feeling about the team at the moment, Pickens was blunt. “That’s a Tyler question.”
A longtime Sky fan, Pickens was simply deadpanning, offering up a tongue-in-cheek acknowledgment of the public tensions between Sky head coach Tyler Marsh and star guard Skylar Diggins. Earlier this season, Diggins directed a reporter to “ask Tyler” about the team’s offensive struggles, creating a mild stir. Similarly, Pickens seemed to lay many of the team’s struggles at the feet of the second-year head coach.
“He’s a little bit too passive for me, and he doesn’t really make quality decisions,” she said, also questioning his development of third-year center Kamilla Cardoso, who frequently flashes star potential but continues to struggle with consistency and foul issues on defense. A college star and national champion at South Carolina, Cardoso is averaging a career-best 14.8 points and 8.8 rebounds per game.
Max Kimble, 33 and a Sky fan of nearly a decade, called Cardoso a “double-double machine,” citing her play as a highlight in an otherwise disappointing year. Still, her status as team leader may say more about the state of the Sky’s roster than anything else.
Entering the home stretch, the Sky are one of three WNBA teams without a player averaging at least 15 points per game. After being acquired in an offseason trade with the Los Angeles Sparks, Rickea Jackson had an average of 18 PPG in four early contests, but she was quickly sidelined by a knee injury that ended her season prematurely, depriving the Sky of a key offensive engine. Injuries also prevented veteran guard Courtney Vandersloot and former Most Improved Player DiJonai Carrington from making their season debuts until June 26 and July 30, respectively.
35-year-old Diggins, a South Bend native and the team’s flagship free agent signing, has been limited due to a knee injury of her own. She has the accomplishments to end up in the Naismith Basketball Hall of Fame at the conclusion of her career. But since she signed in April, she’s been a poor fit for Chicago’s system, posting her worst offensive numbers. The nadir of the Sky’s season may have occurred on July 6, when Diggins publicly slammed Marsh on social media for a reported benching less than a month after bluntly criticizing the team’s “loser mentality” to reporters.
It’s easy to write off such battles as inevitable one-off conflicts, especially during a disappointing season. However, longtime observers note that these chemistry issues extend a larger pattern of “team-versus-star” dysfunction that has seemed to plague the organization for years.
“[Diggins] was echoing every Elena Delle Donne-Kahleah Copper-Marina Mabrey-James Wade-Angel Reese voice from the past who at some point have said the quiet part about the Sky out loud,” veteran basketball commentator Robert “Scoop” Jackson wrote for the Chicago Sun-Times last month.“Skylar just happened to be the one who has said it last and sooner than all of the others who also regrettably have been associated with Michael Alter’s franchise.” Diggins has joined a growing list of big names who have struggled with Sky management.
A real estate developer who has been the principal owner of the Sky since their 2006 launch, Alter has been criticized for his resistance to invest in professional-quality facilities for the team. After years of sharing practice space with the general public at the Sachs Recreation Center in northwest suburban Deerfield, they broke ground in 2024 on a state-of-the-art private practice facility in Bedford Park.
Though a completed practice facility in 2026 was reportedly a part of the free agent pitch used to sign Diggins and Azurá Stevens—the latter generated wide interest around the league after placing second in Most Improved Player voting last year—the team announced in July that they would not utilize the new facility until after this season.
Professional observers like Jackson aren’t the only ones picking up the Sky’s penchant for conflict with players. Lupe Puga, 36, has been a fan for over a decade and became a season ticket holder in 2024.
“I do believe that we need to change to keep players happy and sign longer [contracts],” she told the Weekly when asked about this season’s struggles. “First things first, [make] sure they have a practice facility. I think the org has to be open to more feedback from the players. It all seems so hostile,” Puga continued.
Pickens echoes Puga’s worries about the organization’s hostility and hasn’t forgiven the bizarre handling of longtime WNBA star Teresa Weatherspoon, who was unexpectedly dismissed after just one year as head coach in 2024.
“That crushed the whole chemistry that was already there with her and the franchise player, who was Angel Reese. And that blew the whole thing up,” Pickens said.
Pickens also expressed disappointment in the limited coaching opportunities afforded to Black women in the WNBA. Despite Black women making up the majority of the league’s players, currently none of the league’s 15 head coaches are Black women. In 2025, the WNBA had one Black woman head coach, Seattle’s Noelle Quinn. She was dismissed after that season despite a career record of 97-89 and four playoff appearances in five seasons with the Storm.
The road to the Sky’s current moment of perdition might be dated to July 2023, when then-head coach and general manager James Wade, who had led the Sky to the 2021 WNBA Championship and a league-high of 26 wins in 2022, shockingly departed the team mid-season to take an assistant role with the NBA’s Toronto Raptors. Wade drew heavy criticism for leaving the Sky high and dry, jumping ship just a month after the retirement of franchise icon Allie Quigley and transfers of championship centerpieces Candace Parker and Courtney Vandersloot to more playoff-ready rosters. Current GM Jeff Pagliocca was left with few options with which to rebuild the roster.
Pagliocca’s attempts to maneuver out of the tough hand he was dealt have been largely unsuccessful. In an early attempt to recoup some of the assets dealt by Wade, former Sky star Kahleah Copper was traded to the Phoenix Mercury, where she remains one of the league’s deadliest scorers. Risky trades made to build a playoff contender around 2024 first round pick Angel Reese backfired catastrophically.
“As much as the story of the season has been injuries and losing close games, it’s also knowing the pick that Olivia Miles was taken with originally belonged to the Sky and wondering what could have been,” Kimble said. “That takes up at least half the conversations in my group chats about the team.”
Miles, a guard for the Minnesota Lynx, is an MVP candidate and runaway favorite for Rookie of the Year. She was selected by Minnesota with the second overall pick in this spring’s first-year draft—a selection that would have belonged to the Sky, had they not granted the Lynx rights to the pick two years ago in a deal that originally netted them Reese. The Sky traded Reese to the Atlanta Dream last April in exchange for draft picks in 2027 and 2028.
Playing the what-if game with Miles alone is painful enough. Unfortunately, Sky fans must also consider Sonia Citron, who leads the playoff-bound Washington Mystics with 16.9 points per game. Citron has been named an All-Star in both her seasons after being chosen with the third overall pick in the 2025 draft—a pick that also initially belonged to the Sky but was dealt to the Mystics in exchange for guard Ariel Atkins. Atkins played just one underwhelming year in Chicago, averaging 13.1 points per game last season, before being traded to Los Angeles.
Though it’s been a tough journey for Sky fans since their 2021 championship win, there are promising glimpses of the future. Undrafted rookie Sydney Taylor has been a revelation, emerging as one of the WNBA’s best underdog stories of the year while making the most of opportunities created by the Sky’s depleted roster.
Taylor, now 25, went undrafted in 2024 following her final college season at the University of Louisville. But she earned a training camp deal with Chicago this spring after successful professional stints in Poland and Lithuania.
It only took a few games before she began to see regular rotation minutes; when injuries opened the door for her to shine, she seized the moment. In a breakout performance, Taylor exploded for 30 points in the Sky’s June 11 loss to the Indiana Fever, and she’s been a mainstay in the starting lineup ever since, now averaging a team-high 18.1 points per game.
“The different ways she’s able to score is remarkable,” said Kimble.
A deadly shooter who’s chucking up nearly seven three-pointers per contest this season—and making over 40% of them—the Sky have exclusive rights to negotiate a long-term deal with Taylor at the conclusion of this season’s one-year contract.
With a multi-week break in the WNBA schedule for the FIBA Basketball World Cup starting on August 30, the Chicago Sky’s season is effectively coming to a close. The four games they have scheduled on the other side of the tournament will not restore their dashed playoff hopes. Moreover, they’re guaranteed to send their first round draft pick to the Mystics, as a part of last year’s trade for Atkins.
Nevertheless, those last four games could present new opportunities for strategies to work their way into plans that are formulating for 2027. However they pan out, they will likely hint at how the Sky plan to escape the competitive wilderness they’ve found themselves lost in, three summers in a row.
Malachi Hayes is a Bridgeport-based writer and South Side native.