Chicago Sky Free Agency Preview
With another reset at the head coaching position, the Sky begin their process of building around their young core of Reese & Cardoso.
After a technically short (but seemingly long) quiet period, the WNBA will return en force with the start of free agency on February 1st. Teams can begin negotiating with players as soon as January 21st, and you can expect to hear news about players signing sooner due to qualifying offers being sent out (and sometimes signed) during the first half of January. Trades can also happen in January — so don’t expect this month to be totally quiet.
Before we get into the key storylines facing the Sky this month, let’s remind ourselves of where the roster currently stands (special hat tip to Her Hoop Stats where I double and triple check my own notes on these contract statuses):
Under Contract: Moriah Jefferson, Rachel Banham
Weirdly, the Sky’s only players under a guaranteed contract for the upcoming season are the two rotational players that arrived in the Marina Mabrey trade last July. Both will be out of contract at the end of the 2025 season.
Under Contract (Unprotected): Elizabeth Williams, Lindsay Allen, Angel Reese, Kamilla Cardoso
The nature of these contracts means that the Sky are free to release each of these four with no salary cap punishment. That being said, release is a far from feasible outcome given the stature of these players.
Reserved: Nikolina Milić
Milić, an arrival in the trade that landed the Sky the 7th pick in last April’s draft, remains a reserved player. Thus, the Sky have exclusive negotiation rights with her— meaning the Serbian could not discuss terms with another team unless released by Chicago. With Women’s EuroBasket on the horizon this summer, I see little reason why she’d return stateside in 2025.
Restricted Free Agent: Chennedy Carter, Dana Evans, Michaela Onyenwere
With just six restricted free agents league wide, the Sky will be responsible for most of the “to match or not to match” decisions this winter. Like in most other sports, the Sky can negotiate with these three directly or allow them to pursue other offers and match any signed contract offers at their discretion.
Unrestricted Free Agent: Diamond DeShields, Isabelle Harrison, Brianna Turner
These players are free to negotiate and sign with any team of their choice for the 2025 season. (NOTE: The Sky could use their core player designation on any of these three players this offseason. Because of the estimated market value of these players and their fit with the current direction of the roster, I wouldn’t expect anyone to be cored.)
Key Questions
1. Can the Sky reel in a “big fish”?
Like last winter, this is a key question for the Sky’s offseason. Unlike last time, landing a big name in free agency would allow the Sky to accelerate their timeline for building a championship-minded roster while failing to nab one would carry little consequence with Chicago instead continuing to patiently rebuild around Reese and Cardoso. So, who are the names on the market that could legitimately change Chicago’s 2025 trajectory? Personally, I count 5.
DeWanna Bonner, Kelsey Plum, Satou Sabally, Breanna Stewart, Alyssa Thomas
Signing those players, of course, is a very different story. Thomas and Bonner (presumably) come as a package deal and, while Chicago’s cap situation means they could support reasonable deals for both, I’m not sure the duo will see the Sky as the team that gives them the best chance to claim a ring in the final years of Bonner’s career (she’ll be 38 late next season). Stewart and Plum, on the other hand, are only 30 and could be more interested in the challenge of building to a title with a new franchise, but I still see both returning to their current teams which have claimed the last 3 WNBA titles in tandem.
That leaves Sabally who, on one hand, seems interested in joining Stewart (and her sister) on the Liberty but could also pose cap issues unless Courtney Vandersloot takes a massive pay cut in free agency or leaves the Big Apple this winter. That, of course, is a possibility, but I wonder if it’s a move that makes complete sense for the reigning champions as it may leave them with a surplus of wings, and a lack of proven primary ball handlers at the WNBA level beyond Sabrina Ionescu (who, of course, serves many other roles for the Liberty).
Thus, Sabally seems like the best target for Chicago to aim for. At her best, she offers a more premium version of the dynamic, all-around small forward that Michaela Onyenwere was late last season for the Sky. That said, Sabally’s impact at the defensive end was definitely more muted when she returned from injury for 15 games to end last season. If the decision is between paying Onyenwere in the neighborhood of $100-$125k in restricted free agency or giving Sabally a near max to do an enhanced version of her role, I wouldn’t blame the Sky for sticking with the former Mercury forward and spending the leftover money elsewhere.
Of course, if Onyenwere pushes for a bigger deal or Sabally is willing to give away some of her value to help build a stronger roster, the conversation is a whole lot different. Whatever the case, we may see just how patient the Sky are willing to be with their rebuild if they find out they have a chance to land Sabally this winter. As talented as she is, she’s not the “sure thing” that a player like Stewart would feel like when it comes to elevating your team into the stratosphere of legit title contenders, and it will be intriguing to see how that impacts the way Jeff Pagliocca and other GMs value Sabally this winter. If I had to guess, someone will give her a max offer; so, Chicago will need to go to the same price if they want to acquire her.
Elsewhere, there are a few other big names in free agency that are certainly near the level of the 5 above but don’t quite work for the Sky for one reason or another. Brittney Griner and Nneka Ogwumike are all-WNBA level players but in an area of the floor where the Sky already have their future duo in place. Kelsey Mitchell is a dynamic scorer who would add a lot to the Chicago offense, but I feel there may be a limit to the Sky’s ceiling if they invest max money in her as a high-volume scorer. Lastly, DiJonai Carrington would improve any team in the W, but enters free agency with a restricted designation—meaning Connecticut should use their ample cap space to bring her back.
Of course, names like Jewell Loyd could also continue to circulate on the trade market—offering Chicago a similar chance to accelerate their window towards competing at the top end of the WNBA standings.
2. Does the starting point guard arrive in free agency?
As it stands, it’s difficult to say what direction the Sky will go with their starting five next season. Reese and Cardoso will certainly start, but the other three spots in the starting five are up for grabs. If Onyenwere and Carter return in restricted free agency, they’ll be the odds on favorites to start at the 2 and the 3, but the 1 is likely to be an open competition heading into camp—with Allen, the Sky’s third overall pick and any new arrivals in free agency vying for the last spot in the 5 that open games in 2025. (I have to assume that Evans will leave in free agency).
So, who’s on the market that could give Allen, a reliable veteran, a real run for her money in camp? In truth, there’s not too many realistic names. Vandersloot, of course, is one of the great floor generals in league history but doesn’t fit with Chicago’s current circumstances. Mitchell, as mentioned above, would be a high-powered addition to the offense, but presents obvious clashes with the style of Carter in the backcourt. Meanwhile, various veterans like Sydney Colson, Crystal Dangerfield and Odyssey Sims are available, but none move the needle a whole lot more than Allen. Considering Allen’s team friendly deal ($90,000 in ‘25), all three would demand the same (or more) money to achieve similar (or worse) production.
In other words, the chances of finding a true competitor for Allen next month are limited—with Notre Dame’s Olivia Miles looking like a much more likely option in April’s draft. Of course, the Sky could always pursue a different profile player in free agency or the draft and move Carter to the point guard position. She’s a capable enough passer to initiate the offense, but I question the logic of putting more burden on her shoulders after it seemed the Sky overextended Carter at times late last season with considerable two-way responsibility. Granted, other new arrivals could reduce some of the scoring burden on Carter’s shoulders, but she’s always likely to be a high-volume offensive player at her best.
One final name to keep an eye on is Natisha Hiedeman. I don’t see her leaving Minnesota (especially not for Chicago given her relationship with Courtney Williams), but the former Sun starter is good enough to start once again, and I wouldn’t blame any team for giving her the chance to do so.
3. Who joins Williams in filling out the rotation?
While landing a star may be difficult and the fifth starter could well arrive in the draft, one task the Sky have to complete in free agency is filling out the rest of their rotation. If we assume that the (healthy) starting 5 towards the end of last year plus Banham, Jefferson and Williams return, the Sky need more bodies to fill out their rotation—especially since there’s no guarantee that Jefferson will get regular minutes after averaging less than 9 per game last season. And while it may be difficult to find players good enough to start on the open market, there will always be high-end bench players available given the limited number of W roster spots. A few names that jump out as good options for the Sky include:
Kennedy Burke: Despite struggling from three last season (career low 26%), the 27-year-old was still an important contributor for the Liberty. With the loss of Kayla Thornton in the expansion draft, I expect NY to prioritize retaining Burke, but she’d be a premium bench add for any team (and could reasonably start games depending on the Sky’s final roster).
Myisha Hines-Allen: Another who should sign with a contender but could be a dynamic sixth-player-of-the-year candidate with Chicago.
Tiffany Mitchell: Mitchell is an interesting one as Connecticut have a number of free agents and have to make several directional choices this offseason. She’s good enough to push some of the presumed Sky starters to the bench but would be a value add in any role for Chicago.
Aerial Powers: Like Mitchell, Powers could start in Chicago and can certainly fill it up offensively. She’s another who like (Kelsey) Mitchell doesn’t necessarily fit perfectly with Carter, but her offensive ability matches the Sky’s needs.
Sami Whitcomb: Shockingly, Whitcomb shot just 29% from three last season, but the odds are with her returning to being one of the best shooters in the league in 2025. Again, likely to sign with a contender (including a possible return to SEA).
Kia Nurse: Again, proven veteran with a decent shot (33% 3PT last year) who figures to be one of the top names certified contenders spend time recruiting.
There’s also a number of interesting front court names like Cheyenne Parker-Tyus, Mercedes Russell and Brionna Jones available, but it’s difficult to see any veteran signing on to be the fourth big in Chicago’s rotation given Reese and Cardoso will play heavy minutes and Williams is available to deputize off the bench upon her return from injury.
One thing that’s clear, the Sky’s chances of landing many of these names will jump considerably if the answer to question #1 above is yes. A star joining and validating the chance of Tyler Marsh’s team competing deep into the playoffs in his first year in charge would encourage high-value role players like many of the names above to follow. However, I’d still bet the Sky are at least one year away from landing that big name to support their young front court duo, and a lack of high-profile bench arrivals could be a consequence of that obvious absence of a veteran superstar.
With plenty more to unpack ahead of free agency officially opening on February 1st, I’ll be taking a closer look at these and more questions in the coming weeks:
January 14th: How should the Sky value restricted FAs Onyenwere & Carter?
January 20th: Which of the W’s top free agents could come to Chicago?
January 24th: Where will the Sky’s free agents play next season?