CHICAGO — It’s almost time for the Chicago Sky to be back on the clock for improving their roster.
The Sky will enter the first stage of free agency Saturday — a nine-day window of extending qualifying offers to restricted free agents — that will set the tone for the rest of their offseason roster construction. And with plenty of cap space and a pair of first-round picks in his pocket, Sky general manager Jeff Pagliocca is well-positioned to maneuver in his second free-agency window with the franchise.
So who should be atop the Sky’s free-agent wish list?
The process will be heavily dictated by the Sky’s expectations for 2025. This will not be a championship season. The Sky need to approach it with specific goals: Draft well, develop talent, make the playoffs and — most importantly — transform Chicago into a free-agency destination.
That last step is crucial to accomplish ahead of next offseason, when a new CBA is expected to radically disrupt player movement across the league. And all of this means the Sky can move with plenty of flexibility right now, particularly in offering one-year deals to players who want to test out a new market before cashing in on the predicted increase salaries in 2026.
The Sky ideally need two additions to their frontcourt, both of whom would need to be comfortable coming off the bench behind Angel Reese and Kamilla Cardoso. This disqualifies them from a few key free-agency battles this season, including the race to land Satou Sabally.
The focus, however, is the backcourt. The Sky desperately need to create an identity for their guard play under new coach Tyler Marsh. Their inability to consistently move the ball or shoot from 3-point range last season created one of the most stagnant offenses in the league, which ultimately stunted the growth of both rookies. While it’s easy to overemphasize the importance of a “true point guard,” the Sky need to upgrade their primary (and maybe even secondary) ball handler to look more cohesive.
There are a few big-name guards — namely Kelsey Plum, whom Marsh coached in Las Vegas — whose decisions will command attention over the next few months. But the Sky might be just as well served working in the margins to create consistency on their bench and in the backcourt.
Here are six players the Sky should begin making pitches to on Jan. 21 before they officially can begin signing on Feb. 1.
Chennedy Carter
The Sky’s first priority is negotiating with restricted free agents — and Carter will be at the top of the team’s list. The guard provided a rare bright spot for the Sky last season, leading the team with 17.5 points per game after winning a starting role, but her future with the organization is still uncertain.
Carter’s offensive fit with the Sky is something of a conundrum. She’s clearly a talented shooter, but her heavy emphasis on 2-pointers means she requires a higher usage rate than other comparable guards while failing to provide the kick-out spacing required for a team built around its frontcourt.
If the Sky are going to make Carter work in Chicago, it will require both her willingness and ability to take fewer shots and increase her efficiency, particularly from behind the arc. Her offseason has not entirely reflected those goals — Carter is averaging an impressive 30.7 points in the Women’s Chinese Basketball Association, but she’s taking at least four more shots per game than her WNBA averages while still shooting only 25% from 3-point range.
This will be a hard decision for the Sky, who don’t necessarily want to let the guard walk after such a successful season — but can’t risk another season of lopsided offense.
Michaela Onyenwere
A more cut-and-dry restricted free-agency option is Onyenwere, who stepped into a starting role at the end of last season. Onyenwere is a crucial veteran leader in the locker room for the Sky and offered a lift as a versatile wing who could shoot from long range. Despite technically being unsigned, she spent the early weeks of the offseason participating in team events, which included the introduction of Marsh and the ribbon cutting of the new training facility.
While Onyenwere is expected to return to the Sky, her role is less clear. If the Sky add a few wings through the draft or elsewhere, Onyenwere could move back to the bench and anchor the secondary unit with fellow veteran Elizabeth Williams.
Kelsey Mitchell
The biggest challenge of Mitchell’s free agency will be prying her from the Indiana Fever. While Mitchell said she’s weighing her options heading into 2025, the guard is sitting in a golden situation with a high-caliber coach and a surefire star — Caitlin Clark — in Indiana.
The pros for the Sky are obvious: Mitchell shot 40.2% from 3-point range and averaged a career-high 19.2 points last season, showcasing her ability to space the floor with a strong guard unit and feed an elite post around the rim. But they’ll need to do some pretty tough negotiating to convince Mitchell that she would be in a better spot with the young future in Chicago rather than Indiana.
Natisha Hiedeman
If the Sky are solely looking for facilitation, they should turn their attention north for unrestricted free agent Hiedeman. A six-year veteran, Hiedeman took a reserved role off the bench for the Minnesota Lynx last season. The Sky could offer her a starting gig with the potential to build toward a championship-contending team.
Beyond her ball movement and strength as a defender, Hiedeman generates the bulk of her offense from behind the arc. She is a career 37.7% 3-point shooter — although that dipped to 28% last season — which could bolster an area the Sky sorely need to shore up. Despite her long-range accuracy, Hiedeman is not a high-volume scorer. But if the Sky can create an engine for their offense through the frontcourt and other shooting guards, then a pass-first facilitator like Hiedeman would make sense in a transition season.
Courtney Vandersloot
Y’all ready for some nostalgia? Vandersloot, a two-time WNBA champion and five-time All-Star, is back on the free-agent market and made it clear this week that she’s open to options outside of the New York Liberty. While Vandersloot is past her prime, she’s still one of the best passers in the game — and could offer a short-term solution for the Sky’s backcourt in an important growth year for the franchise.
To make this deal, the Sky would need to feel Vandersloot’s ball facilitation and veteran leadership outweigh her lack of scoring (6.4 points per game with the Liberty last season) and diminished defense. And Vandersloot would have to be willing to return to Chicago — she played the first 12 seasons of her career with the Sky from 2011-22 — in a different role, which could mean some combination of coming off the bench and/or not closing games.
Sami Whitcomb
If the Sky want to take a flyer on a high-volume shooter, Whitcomb could be a perfect option. The Australian guard was one of the most consistent 3-point shooters in the WNBA throughout her first seven seasons, averaging 37.2% shooting on 4.5 attempts in that span.
Whitcomb struggled from 3-point range last season — shooting only 29.2% — as her role fluctuated rapidly from a starter to DNP from week to week. Given her history, it would be unsurprising to see her snap back to her previous consistency as a shooter. And as they look to build around youth, the Sky could benefit from another solid veteran presence on the bench.
