November 15, 2026
November 15, 2026
Chicago Sky’s 2026 Season: A Rebuild Interrupted
Chicago Sky’s 2026 Season was supposed to be the moment the franchise turned the page. A 10-34 campaign in 2025 had ended in frustration and public friction. Over one dramatic week in April, general manager Jeff Pagliocca tore the roster down to the studs and rebuilt it with veterans and young scorers. Second-year head coach Tyler Marsh inherited a new-look team with real promise. What followed was a season defined by injuries, a fractured backcourt and an unlikely rookie who refused to fade.
The Sky did not tinker that spring. They gambled, and the bets reshaped the franchise for years to come.
The defining decision came on April 6, on the eve of free agency. Chicago sent two-time All-Star Angel Reese to the Atlanta Dream for first-round picks in 2027 and 2028. The WNBA’s announcement of the Reese trade landed hard in Chicago. Reese had been the league’s best rebounder and the face of the franchise.
The front office kept moving. On April 12, the Sky sent Ariel Atkins to the Los Angeles Sparks for Rickea Jackson, the No. 4 pick in 2024. ESPN’s report on the Jackson deal also noted a second move. Chicago gave up a 2028 first-round pick to the Washington Mystics for guard Jacy Sheldon.
Free agency brought a wave of experience. Skylar Diggins, a seven-time All-Star, became the franchise’s most notable signing since Candace Parker in 2021. Natasha Cloud, DiJonai Carrington and a returning Azura Stevens followed. Courtney Vandersloot and Rachel Banham re-signed, though Vandersloot was still recovering from a torn ACL.
The draft added UCLA wing Gabriela Jaquez at No. 5. Kamilla Cardoso remained the anchor in the middle. On paper, Chicago had depth, scoring and a clear identity.
Few teams have watched a season pivot so quickly. Chicago opened the year on a four-game road trip and briefly looked like a contender.
The opener at Portland set the tone. Chicago overwhelmed the expansion Fire 98-83. Diggins posted 21 points, 11 rebounds and seven assists. She and Cardoso became the first teammates in league history to each record 20-point double-doubles in an opener. Wins followed at Golden State and Minnesota, and the Sky’s own recap of the opening road trip celebrated a 3-1 start.
The Minnesota win carried a brutal price. Jackson tore her ACL in that game, ending her season after four appearances. She had been averaging 18.0 points and looked like the franchise’s next star. The Sky lost the home opener to Dallas three nights later, with Cloud scoring 18 points in defeat.
The losses piled up from there. A 104-point effort against the Toronto Tempo still ended in defeat, despite 31 assists and 48 percent shooting. Two home losses to Minnesota in a week exposed the other extreme. The Lynx held Chicago to 58 points on May 29, the lowest output of the year. That volatility became a theme. The Sky finished 14th in the league in three-point percentage and 13th at the free-throw line. Chicago went 1-5 in Commissioner’s Cup play, with Diggins scoring 24 points in the lone win over Connecticut.
The close calls stung most. The Sky fell 95-96 to the New York Liberty on June 17. Three nights later, they lost 93-92 at Dallas. By June 22, Chicago sat at 4-12 and needed an answer.
The answer reshaped the roster’s pecking order. It also created a rift that never healed.
Vandersloot returned from her ACL tear on June 26 against Portland. Chicago celebrated with a 124-94 rout, its highest-scoring game of the year. The return should have been a lift. Instead, it scrambled the point guard rotation.
In early July, Marsh moved Diggins to the bench. She objected publicly on social media the next day. Diggins was then placed on the injury list with a knee issue that dated back to Unrivaled. She never played again in 2026, finishing with 14.2 points per game in 19 appearances.
While the backcourt unraveled, Sydney Taylor seized her chance. She had won MVP honors in Poland’s top league before signing a training camp contract. She became a starter in June and never gave the job back.
Taylor erupted for 27 points against Toronto and 30 against Atlanta. Her signature moment came on August 1 against the Las Vegas Aces. With the score tight and seconds draining, she buried a three with three seconds left. Chicago held on 84-83 and claimed a win over the reigning champions.
The rookie’s rise came amid a gritty July. Chicago won at Phoenix, then beat Seattle and Los Angeles in back-to-back home games. The heartbreak never fully stopped, though. The Sky lost 93-91 at Atlanta on July 19 when Jordin Canada beat the buzzer with a layup, then fell 95-94 at New York three nights later. Two more one-possession defeats summed up Chicago Sky’s 2026 Season in miniature: competitive, resilient and just short.
The roster’s depth was tested constantly. Aicha Coulibaly earned a promotion from developmental status in June and gave the rotation 30 games of energy. Banham and Williams absorbed minutes wherever injuries opened holes. Jaquez, slowed by injuries and fatigue as a rookie, still produced a 22-point night against New York.
Taylor delivered again on August 21 against Golden State. Her late three sealed a 73-70 victory at Wintrust Arena. Taylor finished at 13.6 points per game and earned a place on the AP All-Rookie team.
Chicago refused to fold in August. The surge began with an 82-80 escape at Seattle on August 16, a win that snapped a three-game skid. Cardoso anchored the paint while Cloud organized the offense. Cloud, who appeared in 40 games, averaged 11.1 points and 4.8 assists and proved one of the team’s most dependable veterans. A three-game winning streak, including a 93-86 victory over the Liberty, briefly revived playoff hopes.
The run ended at home against Indiana on August 23. Caitlin Clark scored 37 points and Kelsey Mitchell added 30 as the Fever won 113-90. That loss eliminated Chicago from playoff contention with seven games left.
The final stretch offered little relief. A 110-80 home loss to Washington was the worst defeat of the year. Chicago did salvage one last bright moment, beating Toronto 97-85 in its final home game on September 22. Chicago closed at 16-28, fifth in the Eastern Conference, after a 93-101 loss in Washington. It was the franchise’s third straight losing season. The full game log is on the Sky’s Basketball Reference page.
Chicago Sky’s 2026 Season will be remembered as a rebuild interrupted. The Sky lost 128 games to injury, the most in the league. Only Sheldon and Elizabeth Williams played every game. Carrington appeared in just 11. Stevens added 10.6 points and 6.4 rebounds in 32 games.
The disappointments extended off the court. Chicago hosted the All-Star Game, yet no Sky player took the floor. The team’s new Bedford Park practice facility also missed its promised opening. The IX’s season review noted that the delay could hurt free-agent recruiting. Fans still showed up, averaging 8,236 per game across Wintrust Arena and the United Center.
The foundation is not empty. Cardoso averaged 14.7 points and 8.6 rebounds in 43 games, her steadiest season yet. Taylor proved she belongs. Jackson should return as a cornerstone scorer. Marsh pointed to the young core as the clearest positive and promised continued investment.
The Reese trade will shape how Chicago Sky’s 2026 Season is judged. Washington holds swap rights on Chicago’s 2027 first-round pick, limiting the payoff from a poor finish. Reese thrived in Atlanta while the Sky struggled. Chicago bet its future on a fresh start, and that bet still has to be won.
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