Courtney Vandersloot Linked With Return to the Chicago Sky
Should Chicago really be pursuing a reunion with the 2021 title winner? And would the 2024 champ want to return to Wintrust Arena?
After a few years where numerous key players have left the Chicago Sky for greener pastures, it appears one familiar face could be set for a surprising return to Wintrust Arena next season. According to a report from the Chicago Sun-Times’ Annie Costabile, Courtney Vandersloot is among Chicago’s most prominent current targets–with eyes on bringing the veteran guard back to the franchise where she played 12 seasons, garnered 5 All-WNBA team selections and contributed heavily to the franchise’s 2021 title run.
The reported prioritization of a deal for the soon-to-be thirty-six year old follows closely on from the news Costabile shared that Storm G Jewell Loyd is unlikely to land with Chicago in a trade this winter and represents the most significant link between the Sky and a current free agent–save for restricted FA Michaela Onyenwere. As for Vandersloot, her return would definitely be a popular one with the Sky’s fanbase on a personal level but would it make sense from a personnel standpoint? Let’s evaluate why it may not be such a welcome reunion from that perspective.
Lack of Spacing Help
If there’s one thing Vandersloot won’t do, it’s help the Sky spread the floor out and improve their three-point metrics from a season ago. For a team who were among the W’s worst (9th in 3PT%) and most reluctant (last in 3PA) long-range teams in 2024, investing considerable resources in a player who’s only a lifetime 33.7% three-point shooter and has slid to 28.5% in 2 seasons with the New York Liberty should instantly raise a number of red flags.
Of course, there’s always a chance that the veteran can recapture the rhythm that saw her hit a respectable 36% of her threes in her final six seasons before leaving the Sky in 2021, but the trend is clearly headed in the opposite direction. Even if Vandersloot shoots the ball better technically, there’s no promise of a huge upturn in numbers given she would likely see much more difficult looks as part of a Chicago team that (barring other big moves) won’t have the offensive assets needed to poke, prod and create high quality shots like the Liberty (1st in Off. Rating in ‘24) did last season.
With the Sky likely to have two of Angel Reese, Elizabeth Williams & Kamilla Cardoso on the court for virtually every minute of every game in 2025, there’s already going to be concern with spacing the floor. New head coach Tyler Marsh has indicated clear plans to get everyone on the roster shooting the three-ball in some capacity, but that doesn’t mean teams will start to respect any of the bigs (none of whom have much history shooting threes) if/until their threes start falling consistently. And until those defenses react, the spacing is ultimately unchanged. Adding another non-shooter with a heavy rotational role means the dysfunctional offensive basketball the Sky showcased at times in 2024 will likely rear its head at times in 2025—even if Marsh is able to install lots of other new and exciting offensive concepts.
Clash with Other PGs on the Roster
Following on from the lack of spacing is the fact that, in general, Vandersloot provides little noticeable difference from the other guards on the Sky’s roster. At the peak of her career when Vandersloot was a perennial All-WNBA player, she would obviously represent a considerable upgrade over a solid veteran player like Lindsay Allen, but Vandersloot’s game looked a lot more “solid veteran” than “All-WNBA” in 2024 and it’s only practical to expect that trend to continue as she approaches the final years of her career.
Statistically, Allen outperformed Vandersloot in most notable metrics a year ago with the edge the Liberty guard was able to carve out in both rebounds and assists somewhat attributable to the personnel each played alongside. That’s not to say that Vandersloot couldn’t still be a better player than Allen for the Sky in ‘25; rather, it’s to indicate that she no longer represents the notable upgrade over Allen that she would have 24 (or even 12) months ago.
Looking further down the roster, the only other guards currently under contact are the former Sun duo of Rachel Banham and Moriah Jefferson. Banham, of course, represents a notable stylistic departure from any of the other three, but Jefferson is another who plays relatively similar to Allen and Vandersloot. Like the pair, Jefferson is a pass-first player (5+ assists per 36 in ‘24) who didn’t offer much shooting help (21.1% 3PT) last year and doesn’t offer a ton of size on the defensive side (though she’s the smallest of the three at 5’6”). Whether you like or love any of the three guards, optionality is always key in a professional rotation and having each of Allen, Vandersloot and Jefferson on the opening day roster would leave Marsh with very little diversity of approach at point guard. To that point, don’t be surprised if Allen (who’s on a reasonable $95k deal) is traded for a change of pace option in the event Vandersloot does sign as Jefferson ($145k) will be much tougher to offload without attaching draft compensation.
Pedigree
If there’s one thing that Vandersloot has that Allen and Jefferson don’t (at least at the pro level), it’s championship experience as she won the WNBA title for the second-time in her Hall of Fame-level career at the end of last season. Granted, the Sky’s current progress (or lack thereof) with Loyd and other marquee targets suggests that contention won’t be a realistic target for the 2025 season anyways, but there’s still something to be said for having a player with Vandersloot’s wealth of experience around a young core of players that will likely include Reese, Cardoso, Onyenwere and the third pick in April’s draft by opening night.
In what’s largely expected to be a transitional year for the Sky with a new coach who promises to bring a completely new approach, a veteran player like Sloot in the fold could be the difference that allows the young stars to turn their buy-in to Marsh’s approach into tangible results, and a steady hand at the wheel could be what helps the Sky return to the playoffs in short order after 2024 saw them miss out on the postseason for the first time since 2018. With the Sky’s 2026 first-round pick already tied up in a swap with the Minnesota Lynx, the incentive to “tank” is non-existent and gaining playoff experience of any kind would be an obvious success for Marsh’s debut season in Chicago.
So will Vandersloot return?
Crucially, the Sky can give Vandersloot what she may want in the form of a bigger role, a place in their starting line-up or a big pay day. Given their current cap position and the limited pool of players likely to give Chicago a chance in free agency, GM Jeff Pagliocca can happily commit to a high-priced one-year deal with any player who’s interested in coming to town for the ‘25 season. And with relatively few likely to commit to a multi-year deal that stretches beyond the implementation of a new CBA after next season, there’s very limited risk in giving out otherwise risk-laden deals to aging players like Vandersloot that may no longer play up to the price their reputation suggests they deserve to earn.
Meanwhile, on a personal level, Vandersloot is likely wise to the fact that this offseason may be her last chance to register a hefty pay-day with the new CBA on the horizon and Chicago is one of the few teams with both cap and rotational space free for her to absorb.
That being said, it’s also entirely possible Vandersloot doesn’t care about any of those things at this point in her career. While her departure looks somewhat necessary to facilitate a rumored move for Satou Sabally, there’s always likely to be some room for her in the New York rotation if she’s willing to come back on a cut price deal. Similarly, a number of other teams will likely have interest in adding Vandersloot to their 2025 plans (again, at the right price) after her admirable performances in a new role off the bench in the 2024 playoffs.
With those doors potentially open, a reunion may be completely off the cards from Vandersloot’s perspective—especially if her priorities lie solely with winning a title. Similarly, it’s difficult to see how Vandersloot would be open to returning to Chicago before its new facilities open—having spent the last two years training in the state-of-the-art environment the Liberty share with the NBA’s Brooklyn Nets.
Ultimately, the Sky’s interest and ability to offer Vandersloot lots of things she may not find elsewhere means it’s too early to close the door on a reunion, but I would hazard a guess that she ends up playing somewhere other than Chicago next season.