Sky GM Gambles Future Picks for Immediate Wins

Chicago Sky General Manager Jeff Pagliocca has signaled a firm "win-now" organizational ethos, eschewing any plans to tank for future draft picks. This strategy has led to the team trading away its first-round selections in the 2027 and 2028 drafts, notably including a pick swap for 2027 and the direct acquisition of guard Jacy Sheldon for the 2028 pick.

These trades prevent the Sky from accessing potential generational talents like JuJu Watkins and Sarah Strong, who are projected top prospects in upcoming drafts. Pagliocca's commitment to immediate competition, even after three consecutive losing seasons and two playoff absences, contrasts sharply with teams that have landed top picks through tanking. The lottery odds in the WNBA, based on a two-year record, make substantial losing necessary to secure a high lottery selection.

Pagliocca views first-round picks as valuable trade assets and believes a win-now approach is essential for attracting and retaining free agents like Azurá Stevens and Skylar Diggins. While the team did keep its 2026 fifth pick to select Gabriela Jaquez, the overarching philosophy remains focused on immediate success rather than long-term draft positioning. The Sky hope this gamble pays off when their season begins next month.