The Chicago Sky were born in 2006 as a WNBA expansion team, and for their first decade they were the franchise of almosts — talented rosters, early playoff exits, and the nagging sense that the pieces never quite fit. Sylvia Fowles anchored the early years. Elena Delle Donne arrived in 2013, won Rookie of the Year and then an MVP in 2015, and still the breakthrough wouldn't come. Delle Donne forced a trade to Washington in 2017, and the Sky bottomed out. What happened next is one of the great rebuild stories in league history.
What defines the Sky is 2021. The sixth-seeded Sky — a .500 team that barely made the playoffs — caught fire at the perfect moment and ripped through October, beating the Phoenix Mercury in four games to win the franchise's first WNBA championship. Kahleah Copper, the midseason acquisition turned Finals MVP, was unstoppable. Candace Parker, the Chicago native and two-time MVP, came home in free agency specifically to deliver this — and did, winning a title in her first season back. Courtney Vandersloot set a Finals record for assists. Allie Quigley hit daggers. It was the most improbable title run in WNBA history, and Chicago celebrated like it.
The Sky's identity is pure Chicago basketball: tough, physical, defensive-minded, with a fan base that treats the team like the city's own. Wintrust Arena on the Near South Side gives the franchise a true home — intimate, loud, and unmistakably Chicago. The 2021 parade through downtown, with Parker holding the trophy aloft in her hometown, is the franchise's signature image.
The modern era brought the next wave of stardom. Angel Reese arrived as the 2024 number-seven pick — the "Bayou Barbie" from LSU's national championship team — and immediately became one of the league's biggest draws and its most ferocious rebounder, setting the single-season rebounding record as a rookie. Her battles with the Indiana Fever's Caitlin Clark turned Sky-Fever into appointment television and gave the league its most electric young rivalry.
One banner hangs from 2021, and the Sky are building toward the next one — drafting talent, developing an identity, and leaning into a city that has proven it will show up for a winner. Chicago waited fifteen years for its first championship. The plan is for the wait to be much shorter this time.
The fall from 2021 was swift and brutal. The championship core aged out and moved on, and the rebuild never found its footing. Teresa Weatherspoon — the Hall of Famer hired to change the culture — went 13–27 in 2024 and was fired after one season. Tyler Marsh, a well-regarded young tactician, took over in 2025 and inherited a storm: Courtney Vandersloot, the franchise icon who came home, tore her ACL, and the Sky cratered to 10–34, tied for the worst record in the league.
Then came the trade that will haunt this franchise for a decade. In the 2026 offseason, Chicago flipped Angel Reese — the rebounding phenomenon, one of the biggest draws in the sport — to the Atlanta Dream for a pair of non-lottery picks. Reese won Defensive Player of the Year in Atlanta and led the Dream to a franchise-record 30 wins and the semifinals. The Sky, meanwhile, handed the keys to Rickea Jackson — acquired to fill Reese's void — and watched her tear her ACL four games into the season. The absences piled up: Skylar Diggins, the $950,000 free-agent splash, missed time; Azurá Stevens and DiJonai Carrington went down too. The Sky finished 16–28 and missed the playoffs for the third straight year, eliminated before the league even paused for the FIBA World Cup in September.
The cruelest part is the draft board. The Sky don't control their own lottery pick until 2029 — the Mystics hold swap rights for 2027 and outright own Chicago's 2028 top pick via the Jacy Sheldon trade. The No. 2 pick in 2026, which the Sky had traded away in the swap-rights deal they made to move up and draft Reese in 2024, became Minnesota's Olivia Miles — the runaway Rookie of the Year who scored more points than any rookie ever. The No. 3 pick in 2025, dealt away in the ill-fated Ariel Atkins trade, became Washington's Sonia Citron — a second-year All-Star. Chicago traded its future for the present and got neither.
So what remains? Kamilla Cardoso, the 6-foot-7 Brazilian center with All-Star tools, is the cornerstone now — when healthy, a genuine two-way anchor. The 2026 draft brought UCLA's Gabriela Jaquez over national champion Kiki Rice, a pick the coaching staff had essentially given up on by year's end; undrafted rookie Sydney Taylor, on the other hand, played her way into All-Rookie consideration. Fan favorite Kate Martin signed on a developmental deal during the September break. And general manager Jeff Pagliocca, under fire from every direction, has staked his future on Marsh: "It was going to be incredibly unfair to judge someone who has yet to play with healthy rosters as a young coach." The Sky open 2027 with a new set of questions and the same old one: in a league that is exploding, how long can Chicago afford to be irrelevant? One banner hangs from 2021. Right now it feels further away than ever — which is exactly why the next eighteen months will define the franchise.
