Skylar Diggins’ Frustration Shows Sky Issues Remain After Angel Reese Exit
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, starting the season 4-1, Rickea Jackson played like an All-Star, and Skylar Diggins ran the team like the veteran star she is. Diggins was a big get in free agency for the Sky. Chicago hadn’t been a destination for All-Stars these past few seasons.
Since then, things have changed dramatically. Jackson tore her ACL just four games into the season, and Chicago has accumulated a 1-6 record without her.
To make matters worse, the Sky are now right back where they were with Angel Reese last season: the team is losing, and Skylar Diggins, their biggest star, is growing frustrated with the team’s direction—something GM Jeff Pagliocca explicitly said he wanted to avoid in the introductory press conference for Diggins and the Sky’s other additions. The roster may look completely different, but the same issues that caused a rift 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 eleven 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 in the postgame media availability, per the Sky’s YouTube channel.
She also added, “It’s been an extremely frustrating experience.”
When asked about the Sky’s struggle to execute in the halfcourt and halftime adjustments, she said, “That’s a Tyler question. Ask Tyler.”
Those comments don’t inspire a ton of confidence in Diggins’s desire to stay in Chicago long-term if the team doesn’t find a way to turn things around soon. Diggins is 35 years old. She still has plenty of good basketball left in her, but her window of competing for a championship won’t be open much longer.
The Sky gave up too much to be in this position
Losing Rickea Jackson was a tough blow, and the Sky are also still playing without DiJonai Carrington and Courtney Vandersloot. Still, a team that features Skylar Diggins, Natasha Cloud, Azurá Stevens, and Kamilla Cardoso should be better than a 4-7 record that has them sitting well outside the playoff picture. If they continue to lose, they will be in a hole too deep to dig themselves out of.
The worst thing is, the organization gave up too much to build this veteran-heavy win-now team to just continue to lose game after game. In the last few years, they gave up the number-three pick in the 2025 WNBA Draft, lost their second overall pick in this year’s draft to the Minnesota Lynx due to draft day trades to get Angel Reese and Hailey Van Lith, traded Reese to the Atlanta Dream, and waived Van Lith.
The Sky acquired some draft assets in exchange for Reese, but considering how good Atlanta is doing, those picks will be late first-round selections. Chicago doesn’t control its own 2027 first-round pick either. They gave the Washington Mystics swap rights when they traded for Ariel Atkins. The Mystics sit just one spot ahead of the Sky in the standings at the moment, but if JuJu Watkins enters the 2027 WNBA Draft, being a lottery team and not having full control over your own pick could be a franchise-altering gut punch.
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Elaine Blum covers women’s basketball for On SI from Europe. She has been writing about women's hoops since 2023 and holds a Bachelor’s degree in English and Journalism and a master’s degree in American Studies with a focus on women’s and gender studies. She started playing basketball when she was 10 years old and won several league and state championships at the youth and senior level.