The Chicago Sky are grappling with the luxury and burden of options during this free-agency period.
General manager Jeff Pagliocca almost entirely recouped the team’s draft stock over the last year, including securing the Nos. 3 and 10 picks in the 2025 WNBA draft. Now the Sky have to answer a key question:
Is the No. 3 pick more valuable as a trade asset or a draft selection?
This year’s draft is highlighted by two of the biggest stars in the sport: Connecticut guard Paige Bueckers and Notre Dame guard Olivia Miles. But for a team like the Sky seeking backcourt players — preferably lengthy wings with playmaking ability — there’s a sizable drop-off between the second and third picks.
With Bueckers and Miles almost guaranteed to be the top two picks — assuming they enter the draft — the Sky appear likely to select Notre Dame wing Sonia Citron if they keep the third pick. Citron would make an immediate impact with her long-range sharpshooting and defensive skills, but she doesn’t carry the game-changing potential — or star power — of other lottery picks in the 2024 and 2025 drafts.
A decision on trading the pick will hinge upon the Sky’s success in free agency. The roster needs veteran depth. Although the Sky remain heavily invested in building through youth, experience is a necessity for that development to occur. And fielding a starting lineup with two second-year bigs in Kamilla Cardoso and Angel Reese plus one or two rookie wings or guards would be a massive undertaking — especially for first-year coach Tyler Marsh.
While the Sky are set for veteran depth in the frontcourt with Elizabeth Williams, the backcourt could use some bolstering. The front office accomplished the first step of acquiring that experience Wednesday by reaching a deal with longtime Sky point guard Courtney Vandersloot, who will return to the team when free agency opens Saturday after spending two seasons with the New York Liberty.
With Vandersloot secured, the Sky face a difficult decision: Will their backcourt benefit more from drafting a guard or adding another high-caliber veteran?
Signing Vandersloot will immediately upgrade the Sky’s ball facilitation, but she also adds to the team’s lack of 3-point volume. Vandersloot was a consistent 3-point shooter during most of her first tenure with the Sky, but her production behind the arc plummeted in New York, where she averaged less than one made 3 per game over the last two seasons.
Adding another low-volume shooter to a starting frontcourt of Reese and Cardoso means every roster decision the Sky make in the next three months must be predicated on 3-point shooting. Pagliocca already emphasized that he will prioritize lengthy wings with long-range potential in both the draft and free agency.
This draft boasts plenty of shooting potential. Citron is a career 36.7% shooter behind the arc. Maryland’s Shyanne Sellers, another mid-first-round prospect, offers similar 3-point efficiency (34% career). With a skilled development coach in Marsh — who is credited for molding Las Vegas Aces guard Jackie Young into one of the league’s top shooters — investing in one of these young wings might make the most sense.
But if the Sky want a more surefire option on the perimeter, that might have to come through a trade — and at the moment, the front office doesn’t have many tradable assets in the form of players.
Guards Dana Evans, Moriah Jefferson and Lindsay Allen are reasonable options to tag onto a trade to balance out contracts and juice up an offer. But outside of 2024 draftees Cardoso and Reese — both of whom remain untouchable — the Sky don’t have any blue-chip assets on their roster.
That’s where the draft comes in. The No. 3 pick is easily the best trade asset in the Sky’s arsenal. Sure, they could offer future picks, but those hold much less value. The only way they can get other front offices to pick up the phone on a serious deal for a veteran guard is to float the lottery pick.
The Sky would need to target a particular type of trade pairing: a front office looking to move up in the draft, most likely to secure a frontcourt player. Specifically, the Sky could get the most value out of trading with a team looking to jump the expansion Golden State Valkyries at No. 5 for a shot at USC’s Kiki Iriafen, France’s Dominique Malonga or LSU’s Aneesah Morrow.
Trading the No. 3 pick could be navigated in two ways: trading back or completely trading away the pick. For some teams, swapping draft positions might be enough of an offering. For instance, the Sky could pitch a pick swap with the Liberty at No. 7 plus additional assets in exchange for versatile guard Betnijah Laney-Hamilton. That would give the Liberty a shot at Iriafen if they need to build up their frontcourt should Breanna Stewart depart in free agency.
Other deals might require trading the No. 3 pick outright. Would the Minnesota Lynx dip into their expansive backcourt to land a top-four pick? That’s the type of conversation the Sky can unlock by shopping the pick.
These conversations are uncertain because the entire landscape of the league is uncertain. This week’s blockbuster trade between the Aces, Los Angeles Sparks and Seattle Storm threw further uncertainty into the equation. The Sparks sent the No. 2 pick to the Storm, according to an ESPN report, because their front office remained unconvinced that both Bueckers and Miles will declare for the draft.
If those concerns are shared throughout the league, the relative value of a lottery pick might drop heavily from expectations at the end of last season. And several remaining decisions from high-profile free agents — Stewart, DeWanna Bonner, Nneka Ogwumike, Diana Taurasi, Brionna Jones — will inform which teams are seeking the rookie bigs who can be attained with the No. 3 pick.
Ultimately the strength of this draft will lie in the dependability of the players available. Not every pick brings the pop of Bueckers or Miles, but the 2025 class is expected to have staying power in the league, whether it’s savvy forwards such as Iriafen and Morrow or a versatile guard such as Citron. And that consistency extends through the first round, which means the Sky are likely to hit on another productive pick at No. 10.
This is an enviable situation for the Sky. Keep the pick or trade it — either way, they’re better positioned to continue the rebuild than in prior seasons. But how they navigate the weeks before the April 14 draft will determine how quickly they can return to contention.
