Just a few weeks ago, it seemed like the Chicago Sky had made all the right offseason choices. They were winning with their new-look roster, off to a 3-1 start; Rickea Jackson was playing like an All-Star, and Skylar Diggins was running the team like the veteran star she is. Diggins was a big get in free agency for the Sky, a franchise that had not been a destination for All-Stars in recent seasons.
Since then, things have changed dramatically. Jackson tore her ACL in the Sky's fourth game of the season, and Chicago has gone 1-6 without her.
To make matters worse, the Sky are right back where they were with Angel Reese last season: the team is losing, and Diggins, their biggest star, is growing frustrated with the direction, something GM Jeff Pagliocca explicitly said he wanted to avoid at the introductory press conference for Diggins and the team's other additions.
The roster looks completely different, but the same issues that drove a wedge between Reese and the organization are still very much alive.
Skylar Diggins Voiced Her Frustration After the Sky's Loss to the Toronto Tempo
Diggins was visibly, and understandably, frustrated after an 85-68 loss to the Toronto Tempo, the Sky's seventh loss in 11 games.
"We gotta have more maturity and more leadership on and off the floor from the players on the floor and from the staff as well," Diggins said.
She added, "It's been an extremely frustrating experience."
Asked about Chicago's struggles to execute in the half-court and about its halftime adjustments, Diggins said, "That's a Tyler question. Ask Tyler," a pointed deflection toward head coach Tyler Marsh.
Those comments don't inspire much confidence in Diggins's long-term desire to stay in Chicago if the team doesn't turn things around soon. Diggins is 35. She has plenty of good basketball left, but her window to compete for a championship will not stay open much longer.
The Sky Gave Up Too Much to Be in This Position
Jackson going down hurt, no question, and Chicago still hasn't had DiJonai Carrington or Courtney Vandersloot available either.
Still, a roster that has Diggins, Natasha Cloud, Azurá Stevens and Kamilla Cardoso shouldn't be 4-7 and outside the playoff field. Chicago's 98.1 offensive rating ranks third-worst in the league, ahead of only Connecticut and Seattle, and the shooting numbers are just as rough at a 45.4 EFG% and 50.8 TS%. If the losing keeps up, the Sky are going to fall too far back to make up the ground.
And Chicago gave up a lot to put this win-now group together. The pick that became Olivia Miles, the No. 2 selection in this year's draft and already a Rookie of the Month in Minnesota, came from the Sky. So did the No. 3 pick that turned into 2025 All-Star Sonia Citron, which Chicago sent to the Washington Mystics in the Ariel Atkins trade.
That same deal handed Washington the right to swap 2027 first-round picks, so the Sky don't control their own selection that year, either. Chicago also drafted Reese before flipping her to the Atlanta Dream, and waived Hailey Van Lith. The Sky did get draft capital back for Reese, but with Atlanta playing this well, those picks are tracking toward the back of the first round.
Washington is only one spot ahead of Chicago in the standings, and if JuJu Watkins declares for the 2027 WNBA Draft, landing in the lottery without control of your own pick is the kind of thing that can set a franchise back for years.
Skylar Diggins after the Sky loss to the Tempo 85-68 in Toronto. pic.twitter.com/x6VXve2chr
— Just Women’s Sports (@justwsports) June 7, 2026
Chicago Sky Drop Another One Against Toronto
Chicago dropped its third Commissioner's Cup game of the season Sunday, June 7, to the Tempo. The Sky couldn't get anything going early, shooting 26.7 percent in the first quarter while the Tempo hit 52.4 percent. Toronto built a double-digit lead off that hot start.
Chicago settled in a bit in the second, with Jacy Sheldon hitting a pair of 3-pointers. The Sky still went into halftime down 48-33.
Rookie Gabriela Jaquez, back after missing four games with an injury, picked up two steals in the third.
The comeback never materialized, but Aruza Stevens had another strong performance, leading the team with 18 points and 12 rebounds for her second consecutive double-double. Sheldon finished with 10 points, and Jaquez scored 11.
Toronto's balance was key, with five players scoring in double figures. Brittney Sykes led the team with 25 points, seven rebounds, three assists, and one steal. Former Sky forward Isabelle Harrison also played well, hitting 2-of-2 from three-point range and shooting 66.7% overall.
The Sky will return to Wintrust Arena on Tuesday to play the Atlanta Dream. The game starts at 6 p.m. CT and will be broadcast on ESPN.
