What Next for the Sky After Missing the 2024 WNBA Playoffs?
What looked like a cellar-dwelling year for Chicago turned into a push for the playoffs--reenforcing the team's bright future. But what lies ahead this winter?
Despite a valiant effort to reach the WNBA Playoffs for the sixth consecutive season, the Sky’s postseason chase concluded with Thursday’s loss to the Sun and results elsewhere in the W on the final night of the regular season. But before we jump into a reflection on the performance of the Sky as a team and as individuals this season (trust me, there’s plenty of that on the way in the coming weeks—subscribe so you don’t miss it!), let’s look ahead to what figures to be a busy offseason for a franchise that looks to be trending in the right direction heading into 2025 after exceeding almost all preseason expectations with their performance in 2024.
Who will stay and go from the current roster?
Kamilla Cardoso and Angel Reese, obviously, will return for their second seasons in Chicago—with both on their rookie contract through 2026 plus a team option for 2027. Elizabeth Williams, who signed an extension on Thursday to forego her upcoming free agency, is also now in line to return as the Sky’s sixth player, and the all-important third big alongside the two rookies. Lindsay Allen, too, is certain to return (despite her unprotected contract for 2025) because of the value she provides at a salary of less than half ($90,000) the veteran max. Meanwhile, the two arrivals in the Mabrey trade—Rachel Banham and Moriah Jefferson—are both signed to guaranteed contracts for next season. Banham’s deal ($95,000) is affordable; so, she could be dealt quite easily, but I see no reason why Chicago would want to get rid of one of the few shooters they have. Jefferson, because of her $145,000 salary, will be considerably more difficult to move. For all her positives, she failed to carve out a consistent role in Connecticut or Chicago in 2024; so, very few teams will want to add her to their cap table at such a high number. Consequently, she’s likely to return to the Sky next season unless Jeff Pagliocca needs a roster spot so bad he’s willing to eat nearly $150K in dead cap.
The rest of the Sky’s 2024 roster will be a free agent of some kind this winter. Chennedy Carter, Dana Evans and Michaela Onyenwere are all restricted free agents—meaning the Sky can match any offer issued by another WNBA team. Carter and Onyenwere, based on their play this season, seem virtual locks to return—with the Sky’s ample cap space meaning they can easily match any and all offers the pair receives. Evans is quite different—with her inconsistent role in 2024 meaning she’s likely to play elsewhere next season. As for the unrestricted free agents (Harrison, Turner, DeShields and Davis), few seem likely to return. Harrison and Turner are dependable veterans who presumably see the writing on the wall as far as their role with the Sky’s young duo and Williams set to eat up the majority of the 2025 front court minutes. Harrison, despite a clear ability to coexist with both of the rookies on court, likely took note of how her role had already evaporated before Reese’s season ending injury—even without Williams in the rotation. DeShields and Davis, finally, are tough to judge—with both likely fringe WNBA players in 2025.
What about the coaching staff and front office?
Given Jeff Pagliocca and Teresa Weatherspoon only arrived last offseason and their first season outperformed expectations, there’s no reason to expect any changes with the key pieces of the Sky’s braintrust. Changes on Weatherspoon’s staff are definitely possible as assistants come and go pretty regularly from year to year, but I wouldn’t expect any big shake ups as, again, this is a new staff that performed well in its first season together. The one thing I would watch is if the Sky might give Weatherspoon an extension after her successful first season as a WNBA head coach.
Different people will inevitably have different opinions about just how good of a coaching job the former Pelicans assistant did in her first season, but I think the overall reviews should be mostly positive (though, I read social media and know they’re not). The rotations (a hot topic in my blogs) definitely could use work, but that’s natural for a first-time professional head coach with the amount of change the roster underwent due to injury and trade throughout the season giving Weatherspoon very valid explanation for some of the issues. Beyond that, her performance of the administrative duties we typically associate with being a head coach (timeout management, after timeout plays, etc.) was at worst satisfactory and often quite good while her player management was, as expected, her greatest skill. She clearly built strong emotional connections with the Sky’s players, and a lot of basketball coaching ultimately comes down to how much the players like you and will buy in. That can’t be your only skill of course, but it’s extremely helpful to be a master of it like Weatherspoon is.
So, with that said, there’s valid reasons to consider an extension if the deal Weatherspoon signed last offseason was a short one. Unfortunately, we’re a bit in the dark on the length of deal she signed (the WNBA needs to get better on stuff like this), but it wouldn’t shock me if it was a shorter 2-3 year deal to protect all parties involved at the time of signing (remember, the Sky hadn't confirmed their practice facility’s construction when Weatherspoon was hired). If that’s the case and Weatherspoon could be a free agent after the 2026 season (or especially at the end of 2025), it makes sense to extend her through 2027—aligning her deal with Reese and Cardoso’s. Weatherspoon is popular with both players and, even if the Sky did want to go in a different direction before ‘27, the buyout shouldn’t be a huge obstacle with the way WNBA revenues are growing. Of course, it’s no secret that much of the Sky ownership is—shall we say—thrifty; so, I’m not sure they’ll see this situation in the same way. Regardless, all parties seem happy right now; so, an extension should be easy to hammer out whenever it comes time. Yet, I still think it’s at least worth considering as you never know what can change and Spoon will certainly be a candidate for other jobs (especially with the various new expansion teams) in the future if there’s any inclination that she would consider leaving Chicago.
What players could arrive in free agency?
I talked about this back in August, but I don’t see too many of the big fish on the free agent market being keen on Chicago at this stage in the team’s retool. The promise the Sky’s young core showed in 2024 could convince a player like Satou Sabally to at least consider a move to the Windy City (especially given the lack of a clear trajectory in Dallas), but the timing doesn’t feel right for the German or other big names coming from championship situations like Breanna Stewart or Kelsey Plum. In short, Chicago is still inexperienced and without a shiny new (or self-owned) practice facility, and time is the only thing that can change either of those truths. By 2026, we may be having a very different discussion about the Sky’s free agency prospects, but we’re probably not there yet. That being said, all it takes is one. A single marquee free agent choosing to come to a Chicago a year early would open the floodgates for other top options to follow, and the Sky front office will have to think that Reese, Cardoso and Weatherspoon are all strong enough recruiters to convince someone significant to join sooner or later.
What are the implications of the draft lottery?
I talked about this at length a few weeks back when Angel Reese was ruled out for the season, and the scenarios haven’t changed much since then. The lottery, as a reminder, is based on a two-year cumulative record, and the Sky and Dallas—the team who Chicago owes a pick swap to—are likely to finish with the same two-year record if the Aces beat Dallas later on Thursday night. If that’s the case, the 2025 record will act as a tiebreaker—meaning Dallas will get the second best odds for the top pick, and the Sky will get the third best odds. Here’s the table with the complete breakdown of odds for the four lottery teams:
And here’s where things stand (with Dallas, again, playing later against Vegas):
In short, the only thing we can say for certain is that the Sky will not have the top pick. Otherwise, the Wings having better odds at the top spot means, in theory, the Sky are in a much better position as far as the swap than it seemed would be the case in the preseason when Dallas looked a surefire playoff team. Beyond the Sky hitting on their 18% chance and claiming the top pick, there’s very few true doomsday outcomes, and the more likely reality is they’ll move down 1 spot in the draft order at most as a result of the last piece of James Wade’s infamous trade for Marina Mabrey. Whatever the case, Chicago will be hoping that both they and Dallas fair well in the lottery draw—with the Sky still able to pick as high as second even post-swap if all falls favorably. Regardless, the Sky are most likely to pick third (with or without the swap) as Chicago and Dallas have a combined 68% and 61.7% chance at the second and third selections.
Is another active winter on the trade market coming?
Much of this likely depends on how the aforementioned lottery falls. Picks 2, 3 and 4 may all end up holding considerable value depending on how this draft class’ stock ebbs and flows over the course of the college season, but a higher pick will obviously always be worth more to more teams—especially if it’s the second overall selection (behind presumed number one pick Paige Bueckers). Beyond that, the Sky don’t have too much highly-valuable draft capital to work with. They’ve already dealt swap rights for their 2026 first-rounder in the deal that landed them Angel Reese in the 2024 draft, and the first-rounder they got in the Marina Mabrey deal is Connecticut’s first-rounder in April’s draft (2025)—meaning it will come at the back end of the first round after the Sun’s third-place finish in the regular-season standings. The 2025 draft looks strong, but it’s not as heralded as the 2024 class—meaning that pick is unlikely to get too much buzz when it comes to acquiring high-value veterans.
Similarly, the 2026 first-round choice that the Sky acquired from Phoenix in the Kahleah Copper trade is not one that’s likely to hold huge value at present given the high degree of uncertainty around how Copper and the rest of Nate Tibbetts’ team will perform in their second year in the Valley. In truth, that’s a pick that the Sky are likely better off holding onto—with hopes that an unexpected slide in 2025 from the Mercury enhances the pick’s value ahead of a ‘26 draft including high-profile players like Raegan Beers and Lauren Betts. Chicago also holds a pick swap with Connecticut in that same 2026 draft, but the aforementioned swap they owe to the Lynx that year (and the Sun’s huge group of pending free agents) means it’s virtually impossible to figure out where that pick might wind up. Regardless, I don’t see any of the picks Chicago holds (other than lottery selection in the ‘25 draft) being enough to bring in the type of veteran they’d need to considerably upgrade the roster in the present. Similarly, the players Chicago currently has under contract are also not likely to draw a huge return—with the exception of the rookie front court players (that they obviously won’t be willing to deal). Thus, the only trades I’d expect to see Chicago make would fall into one of the three categories below:
Packaging picks to move up in the draft.
Chicago could tie the ‘25 Connecticut pick or the ‘26 Phoenix pick to whatever ‘25 lottery pick they end up with to move from 3 or 4 up to 2. This only makes sense if Pagliocca is heavily sold on one particular player like he was with Reese last April. The Sky’s current assets are not enough to get to #1 and select Bueckers.
Packaging picks to acquire a mid-tier veteran.
Chicago could use some/all of their owned picks to get a solid veteran supporting piece that would accelerate their window to win now. This would be (in some ways) reminiscent of the Mabrey trade that former GM James Wade made in 2023 and doesn’t really make sense for the roster’s current trajectory.
Moving down to stockpile assets.
The alternative to #1 sees the Sky let someone else move up if they’re not sold on anyone in the top 4. Whatever they do with their eventual lottery pick, I’d be surprised if Chicago didn’t at least try to move the Connecticut pick as a future asset will always feel more valuable than someone they pick at the back end of the first round who might get cut in camp.
Whatever the circumstances, the key for the Sky’s front office is to avoid hastily committing future assets (like they did in the trade for the Reese pick) or giving away the assets they do have at discounted value (like they did in the trade that shipped Mabrey to Connecticut). Stockpiling assets and then being aggressive with the ones you’ve gathered is great, but it can’t always come at the expense of fair market value for players and picks. Given where things stands, I personally don’t see the window for Chicago to make too many deals (besides scenario #1 above which is always possible), but I think Pagliocca will be active in searching the market anyways as this free-agent class doesn’t present many options to quickly boost his team’s roster for next season.
Thanks for the constant great coverage