Sky Trades Away Lottery Picks, Prioritizes Winning Now

Chicago Sky GM Jeff Pagliocca makes bold moves to build a contender, sacrificing future draft capital.

Apr. 18, 2026 at 9:39am

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A fragmented, cubist-style painting depicting a WNBA basketball game, with the players and court broken down into sharp, overlapping geometric shapes in shades of blue and orange, conveying the high-stakes gamble of the Sky's win-now strategy.The Chicago Sky's bold moves to build a contender now rather than tank for future draft picks could pay immediate dividends but also carry long-term risks.Chicago Today

The Chicago Sky have traded away their first-round picks in the next two WNBA drafts, including potential lottery picks that could have landed them transformational prospects like JuJu Watkins and Sarah Strong. Sky GM Jeff Pagliocca is prioritizing winning now over rebuilding through the draft, believing his team can contend immediately with key free agent signings like Azurá Stevens and Skylar Diggins.

Why it matters

The Sky's moves highlight the difficult balance WNBA teams face between building for the future and competing in the present. Passing up potential franchise-altering talents like Watkins and Strong is a risk, but Pagliocca believes the Sky can win now and doesn't want to tank, even if it means sacrificing high draft picks.

The details

The Sky traded their 2027 first-round pick to the Washington Mystics last year as part of the Ariel Atkins deal, and then sent their 2028 first-rounder to the Atlanta Dream last week for guard Jacy Sheldon. This means the Sky won't have a first-round pick in the next two drafts, which are expected to feature can't-miss prospects Watkins and Strong. However, Pagliocca is confident the Sky can win now with their current roster and free agent additions, rather than trying to bottom out for a high draft pick.

  • The Sky traded their 2027 first-round pick to the Mystics last year.
  • The Sky traded their 2028 first-round pick to the Dream last week.

The players

Jeff Pagliocca

The general manager of the Chicago Sky, who has made bold moves to build a contending team rather than tank for high draft picks.

JuJu Watkins

A projected No. 1 overall pick in the 2027 WNBA Draft, considered a transformational, pro-ready star.

Sarah Strong

A projected No. 1 overall pick in the 2028 WNBA Draft, also considered a transformational, pro-ready star.

Azurá Stevens

A free agent signed by the Sky this offseason to help the team contend immediately.

Skylar Diggins

A free agent signed by the Sky this offseason to help the team contend immediately.

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What they’re saying

“We're going to remain in win-now mode as long as I'm here.”

— Jeff Pagliocca, Chicago Sky General Manager

“They need to feel confident that we're going to build a team around them.”

— Jeff Pagliocca, Chicago Sky General Manager

What’s next

The Sky will look to build on their recent free agent signings and contend for a WNBA championship this season, despite lacking high draft picks in the coming years.

The takeaway

The Sky's bold moves to trade away future first-round picks show their commitment to winning now rather than rebuilding through the draft, even if it means potentially missing out on transformational prospects like Watkins and Strong. It's a high-risk, high-reward strategy that could pay off immediately if the Sky can contend, but also carries the potential for long-term consequences if the team struggles.