General manager Jeff Pagliocca isn’t leaving the Chicago Sky’s future success up to lottery luck.
The Sky don’t own their first-round pick in the next two drafts thanks to separate deals with the Washington Mystics. Pagliocca included a pick swap in 2027 as part of last year’s trade for Ariel Atkins, a deal that also included sending the No. 3 pick in 2025 to the Mystics — and ultimately concluded with the Sky’s acquisition of Rickea Jackson last week in exchange for Atkins. The Sky traded their 2028 first-rounder last week for guard Jacy Sheldon.
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Lottery picks are consequential in any draft, but the 2027 and 2028 lotteries hold a different weight because of projected No. 1 picks JuJu Watkins of USC and Sarah Strong of Connecticut.
Both players are considered transformational, pro-ready stars whose arrival in the WNBA has been anticipated since before they even made their college debuts. This might feel a bit repetitive in a league that welcomed No. 1 picks Caitlin Clark in 2024 and Paige Bueckers in 2025, but Watkins and Strong are dynamic players who should be instant stars.
Without owning their first-round pick in either draft, the Sky don’t have a likely path to landing either star, unless both the Sky and Mystics miss the playoffs this year. The Sky do own the Atlanta Dream’s next two first-rounders from the Angel Reese trade, but the Dream are projected to be title contenders with their picks likely falling well outside the lottery.
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The Sky finished in the lottery the last two years after going a combined 23-61 in 2024 and ’25. If this trend continues, by trading away his upcoming first-rounders, Pagliocca risked pulling the Sky out of contention for either Watkins or Strong.
Why? The short answer comes down to organizational ethos. At his core, Pagliocca doesn’t believe in planning to lose. The Sky won’t tank under this front office, something he has emphatically stated since he was hired after the 2023 season.
“We’re going to remain in win-now mode as long as I’m here,” Pagliocca said Wednesday in a news conference introducing new players.
It’s important to understand how much losing is necessary to land a No. 1 pick in the WNBA. The Sky have yet to have the top pick after more than two decades in the league — and for good reason. Teams such as the Dallas Wings (2025-26) and Indiana Fever (2023-24) that landed back-to-back No. 1 picks did so by losing at an alarming rate.
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First, a team has to be one of the seven teams to miss the playoffs (and it was five teams last year and four before that pre-expansion). But unlike the NBA, draft lottery odds are based on a two-year record in an effort to prevent serious tanking. That means the Sky likely would have had to lose 34 or more games each of the next two seasons to make a 2028 lottery pick worth their while.
It’s important to understand the sequencing of these decisions. The Sky aren’t suddenly trying to win because they don’t want the 2027 pick swap to be triggered; Pagliocca made that trade because he didn’t believe the Sky would finish behind the Mystics and felt they weren’t risking the loss of a higher draft pick. It’s a simple gamble but an essential one.
After three straight losing seasons and two straight out of the playoffs, the Sky never were going to settle in for tanking regardless of the quality of the potential No. 1 picks. Tanking is a risk in the WNBA, in which the drop-off between a No. 1 and No. 5 pick is often significant. It’s even harder during expansion seasons, when new teams often finish at the bottom of the standings because of a lack of experience and depth.
But still, a team should keep its own first-rounder as a fallback plan, right?
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Even if a front office isn’t attempting to build through the lottery, first-round picks are crucial bargaining chips in future trades. And a 2028 pick with the possibility of being a lottery pick could gain value if Watkins (or other top-rated players) opt to stay in college for an additional year. On the flip side, the Sky’s pick could begin to devalue if they win enough games this season, deflating their potential lottery odds.
There are risks either way. If the Sky miss the playoffs this year and the Mystics don’t, the Sky will be sending away another lottery pick. Perhaps a better offer could have been found with a little more patience.
But Pagliocca is a dealer, an executive who prefers to stay on the move and keep busy on the phones — and, at times, perhaps take on extra risk as a result.
“I don’t know, sometimes the mood strikes me and you’ve got to go make a move,” Pagliocca joked.
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This style can hurt the Sky. That was clear in this year’s draft, when the Sky wound up forking over the No. 2 pick to the Minnesota Lynx as a result of the 2024 trade to move up one spot and draft Reese. A 10-34 season in 2025 was hard enough; not recouping the silver lining is even worse. And that deal stings even more given how short-lived Reese’s tenure in Chicago ultimately became.
But Pagliocca couldn’t let that lost venture cloud his guiding principles. And no matter the allure of future draft picks, planning to lose doesn’t appeal to free agents.
Pagliocca knew as much when he began pursuing Azurá Stevens and Skylar Diggins at the start of free agency. Both players held personal reasons to come to Chicago, but neither would have bought in without faith that the Sky were committed to winning immediately rather than hedging their bets on the long term.
“They need to feel confident that we’re going to build a team around them,” Pagliocca said. “I don’t want to deal with Skylar Diggins every night if she doesn’t have players that she can go to war with. We made sure they understood the vision.”
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The front office isn’t entirely averse to building through the draft. Pagliocca said the Sky never considered dealing this year’s No. 5 pick, feeling certain that UCLA’s Gabriela Jaquez was an essential fit for the roster, especially after landing their top free-agent targets. But the Sky aren’t hoping to hit on No. 1 — something that won’t change with Pagliocca at the helm.
If this team starts winning, the gamble would pay off immediately. The Sky hope to begin collecting on that bet when the season starts next month.
