Chicago Sky land No. 5 overall pick as rebuilding effort continues

Chicago entered the draft lottery with just a 5.5% chance of landing the No. 1 pick. Sky co-owner and operating chairman Nadia Rawlinson represented the Sky at ESPN’s studios for the lottery reveal. Rawlinson was the only member of a front office to represent a team this year — the Minnesota Lynx, Washington Mystics, Seattle Storm and Dallas Wings all had players present.

How the Sky landed the No. 5 pick is a bit of a tale in itself. They gave the Lynx the right to swap 2026 first-round picks as part of a draft-day trade in April 2024. Another trade a year later gave the Lynx the pick outright in exchange for a 2025 draft pick that became guard Hailey Van Lith. The Lynx came away with the No. 2 overall pick in Sunday’s lottery.

A third trade got the Sky back in the 2026 lottery and ultimately gave them the No. 5 pick. In July 2024, the Sky acquired the right to swap Phoenix’s 2026 first-round pick, which they already owned, with Connecticut’s. That was part of a deal where the Sky received Rachel Banham and Moriah Jefferson and traded away Marina Mabrey.

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But the No. 5 pick is not likely to be the cornerstone of the Sky’s continued rebuilding effort. Seven members of the Sky’s roster are unrestricted free agents, and it’s not yet clear who the Sky will choose to protect when the expansion draft comes around this winter. General manager Jeff Pagliocca has also signaled that the organization may consider overhauling the roster. That uncertainty makes it hard to predict which direction Chicago will go come April. The Sky declined to make any members of the front office available for an interview following the lottery.

The Sky desperately need sustained leadership at point guard. After veteran guard Courtney Vandersloot tore her ACL in June, Chicago struggled to run their offense efficiently. Although Vandersloot is expected to return this season, at 36, the team can’t rely on her to carry the offense long term, and the team needs to invest in acquiring and cultivating talent at the one.

The Sky’s two-time All-Star Angel Reese did not give exit interviews this year, and it’s unclear whether she will stay in Chicago to finish out her rookie contract. Although Pagliocca and head coach Tyler Marsh have both expressed their support for Reese, her status with the team is one that could greatly impact the rest of the Sky’s offseason moves.

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Chicago has relied heavily on Kamilla Cardoso and Reese to create offensive opportunities inside. If the “Skyscrapers” duo is broken up, that could change the team’s focus from looking for a young ball handler to looking for someone who can create offense in the post.

If history is any indicator of where the Sky may go, last year the team picked up Van Lith, a point guard, in the first round. Using the first edition of The IX Basketball’s 2026 Draft Board, prospects that could be around for the Sky to select at No. 5 include UCLA point guard Kiki Rice, LSU wing Flau’jae Johnson and UConn off-ball guard Azzi Fudd.

Editor’s note (Nov. 24, 1:30 p.m. ET): An earlier version of this story was not specific enough about how the Sky ended up with the No. 5 pick. More details about the trades with the Lynx have been added for clarity. The story has also been updated to clarify that the pick swap with the Sun involved Phoenix’s 2026 first-round pick, not Chicago’s.

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