The Chicago Sky are entering the 2026 WNBA season with a drastically different look following a series of aggressive roster moves. After finishing the previous season with a 10-34 record and facing scrutiny for trading Angel Reese to the Atlanta Dream at the start of free agency, the organization pivoted toward a veteran-led overhaul.

The centerpieces of this new-look roster include seven-time All-Star Skylar Diggins, who signed a two-year deal to provide a high-level playmaking presence in the backcourt. Joining her is Rickea Jackson, who was acquired from the Los Angeles Sparks in a one-for-one trade for guard Ariel Atkins. Jackson, entering her third season in the league, brings a scoring average of 14 points per game and a reliable perimeter shot to the Sky’s frontcourt.

The Sky also prioritized defensive versatility by signing DiJonai Carrington to a one-year contract. Carrington, the 2024 Most Improved Player and an All-Defensive First Team selection, spent the first four years of her career with the Connecticut Sun. She brings significant postseason experience to Chicago, having played in 25 playoff games while establishing herself as one of the league's elite perimeter defenders.

The Sky also secured a familiar face by bringing back Azurá Stevens after her three-season stint with the Sparks. The 6-foot-6 forward adds length and interior scoring alongside Kamila Cardoso.

Despite holding the worst record last season, the Sky do not own the No. 2 overall pick in tonight’s draft due to a 2024 trade with the Minnesota Lynx; however, they still hold the No. 5 overall selection. With a lineup that now features a mix of elite shooters, lockdown defenders, and veteran leadership, the Sky have positioned themselves for a complete cultural and competitive shift heading into the new campaign.