As Chicago Sky remember their glory days, will they do what it takes to return to WNBA relevance?

CHICAGO — Standing with her wife Courtney Vandersloot, surrounded by family and her college coach, Allie Quigley watched as a banner with her name and number was hoisted into the rafters of Wintrust Arena on Wednesday night. Quigley’s 14 was the first number retired by the Chicago Sky in the organization’s 20 years in the WNBA.

Quigley played for the Sky for 10 seasons and was named an All-Star three times. She was known for her quick-fire shooting, especially from behind the arc, and won the WNBA 3-Point Contest three times. Most importantly, she helped the Sky win their first WNBA championship.

The Sky gave Quigley a memorable night, with videos from former Sky stars and coaches, a speed painter recreating a photo of Quigley celebrating the team’s championship, and speeches from Vandersloot and Michael Alter, the team’s owner. The team was also kind enough to pull out an 87-76 win over the Dallas Wings, with Rebecca Allen knocking down five 3-pointers.

But in some ways, the jersey retirement for Quigley was a reminder that those championship days are well in the past. The only person from that team who is still on the Sky’s roster is Vandersloot, who tore her ACL earlier in the season and won’t play again this year.

CHICAGO, ILLINOIS - JULY 09: Former Chicago Sky player Allie Quigley watches as her jersey is raised during her Jersey Retirement ceremony at halftime between the Chicago Sky and the Dallas Wings at Wintrust Arena on July 09, 2025 in Chicago, Illinois. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement.  (Photo by Michael Reaves/Getty Images)
Allie Quigley was a key player on the Sky’s 2021 championship team, but those glory days seemed far away on Wednesday night in Chicago. (Photo by Michael Reaves/Getty Images)
Michael Reaves via Getty Images

Now, Angel Reese is the face of the team. This week, she was named to her second All-Star Game in as many seasons in the league, introduced her first signature shoe and was named the cover athlete for the NBA 2K26 WNBA Edition. She’s been in a tear on the court, notching double-doubles in the last seven games, but that hasn’t always translated into wins for the Sky. The team is 6-13, ranked 10th in the league, and is 4-6 in the last 10.

Tyler Marsh, the team’s first-year head coach, said he sees signs of improvement daily with his young team.

“My perspective is always going to be a little bit different than from the outside, being the coach here, and seeing everything day to day, and the work that gets put in, and the progress you’re able to see, the incremental progress that’s there,” Marsh said before Wednesday’s game. “Sometimes as outsiders or as fans, you only see what you see, and you’re judged off your wins and losses, and we understand that as part of the business that we’re in, but for us there’s a bigger picture to it. And sometimes, when you’re trying to build something great, when you’re trying to build something sustainable, you got to go through the mud first.”

The Sky have been through plenty of mud. They’ve a hard time stringing wins together all season. After two seasons in New York and a 2024 championship, Vandersloot was brought back to the Sky in the offseason as a veteran presence for the young team. When she was injured in the Sky’s loss to the Fever in early June, it took time for the Sky to regroup without their point guard.

But there have been positive moments, too. Reese’s play has shown improvement, even from her breakout rookie season. Kamilla Cardoso, the Sky’s top pick last season, had breakout performances before she had to miss games to play for the Brazilian national team at AmeriCup.

But that doesn’t mean the Sky look headed for the playoffs. What ails them goes well beyond the players on the team or even the coach. They’ve failed to attract big-name free agents outside of Vandersloot. Off the court, they’ve lost well-respected team employees to other organizations, and even moments like the team’s 20th anniversary have felt half-done. The team announced there would be a special logo on the court for the anniversary, and it’s yet to appear. 

But no problem has loomed larger than the Sky’s lackluster facilities.

Former players have not been shy speaking out about their problems playing for the team. The WNBA is not a large league, with just 156 players, so it’s never been a secret that the Sky’s facilities lag behind other teams. The team practices at Sachs Recreation Center, a park district facility in the northern suburbs of Chicago that’s nearly 30 miles from the team’s arena.

In 2021, Candace Parker returned to her hometown of Chicago to help the Sky win a title. But in 2023, she told Draymond Green on his podcast about how she’s never had her own locker or facility where she could put up shots at night until she signed with the Aces, who built a state of the art facility for the team.

Last season, when Gabby Williams was returning to the WNBA after helping France win a silver medal at the 2024 Paris Olympics, Reese tried to recruit Williams back to the team that had drafted her. Williams responded on X, “Orrrr we could just play together for a different organization.”

The Minnesota Lynx’s Courtney Williams, who played for the Sky in 2023, spoke candidly in a recent live stream about how the team’s facilities didn’t have private locker rooms, and how the rec center’s location is a problem with Chicago’s notoriously bad traffic. Players are housed near the facility, while the team’s arena — which belongs to DePaul University — is just south of Chicago’s Loop. She said the team would give them day rooms in hotels near the arena between shootaround and games, but they wouldn’t pay for overnight accommodations.

“If we’re tired from a game and I’m exhausted and I want to do my recovery or even if I want to just go hang out in downtown Chicago, why don’t you all have me a room, bro?” Williams said. “… and then if I want to hang out, I have to pay for my hotel room.”

The Sky’s ownership broke ground on a new facility in October 2024 in a partnership with another suburb, Bedford Park. The promise was that the Sky’s players would be able to use the new facility in time for the 2026 season, but the Chicago Tribune reported the facility was running behind earlier this season. The team is still confident that the facility will be open in time for next season. While the Sky advertised the facility as state of the art, they didn’t solve the location problem.

Bedford Park, a small, industrial suburb near Midway Airport is still a 14-mile drive to the Sky’s arena. While that’s shorter than the current 27-mile commute from Sachs, anyone who has flown into Midway will understand that players will still have a considerable commute to Wintrust. Compare that to Minnesota, whose players practice across the street from the Target Center.

Elsewhere in Chicago, the MLS’ Chicago Fire’s ownership just announced a $650-million privately funded stadium on a vacant piece of land just 1.5 miles away from Wintrust, the Sky’s home. MLS players are seeing the Fire’s owners make an investment in not just the team, but the city.

The teams that have played in the last two WNBA Finals, the Aces, Liberty and Lynx, are teams well-known for significant investments in their organization. New York recently announced plans for an $80-million, 75,000-square-foot practice facility in Brooklyn. 

It’s clear the Sky need to invest more into the team if they want to raise more banners into the rafters. If the current ownership can’t or won’t make the same kind of investment, they need to sell.

Otherwise, they will continue to spend time looking back on the 2021 season, raising banners for retired players instead of future championships.

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