Ahead of the 2023 season, the Chicago Sky and then-general manager and coach James Wade made the short-sighted decision to trade two first-round picks, a first-round pick swap, two second-round picks, a third-round pick and the rights to Leonie Fiebich for Marina Mabrey.

The last of the draft capital from that disastrous deal was due last spring, and proved especially costly. Despite ending up in the lottery after a 13-27 season in 2024, the first-round swap they owed the Dallas Wings guaranteed they could not get the No. 1 pick and the opportunity to draft Paige Bueckers in the 2025 WNBA Draft.

The Sky wound up with the No. 3 pick, but instead of adding another top prospect to their young core of Angel Reese and Kamilla Cardoso, they repeated the same mistake they made with the Mabrey trade. General manager Jeff Pagliocca sent the third pick — which eventually became Sonia Citron, who finished second in Rookie of the Year voting — a 2027 first-round pick swap and a 2027 second-round pick to the Washington Mystics for Ariel Atkins.

Chicago’s win-now scheme, which also included adding a number of other veterans, such as Courtney Vandersloot, Kia Nurse and Rebecca Allen, collapsed almost immediately. They started 0-4, lost Vandersloot to a torn ACL in early June and eventually finished in 12th place at 10-34, which was tied for the worst record in the league. Their .325 winning percentage was the second-worst in franchise history and together with the Wings (also 10-34) they set the league’s new single-season losses record.

To make matters worse, the Sky do not own their own first-round pick this year because of previous trades made by Pagliocca, and could give away the No. 1 overall selection to the Minnesota Lynx, who are the favorites to win the title. The Sky will, however, wind up with a lottery pick because they own the Phoenix Mercury’s first rounder and have swap rights with the Connecticut Sun’s first rounder. (They’ll get the more favorable of the Mercury/Sun picks.)

If all of the above wasn’t bad enough, the Sky appear to have alienated Reese, who gave a controversial interview about her frustrations with the organization, both on and off the court, and was subsequently suspended for one half of a game. She never played again after that ruling and sat out the remainder of the season with a back injury, then skipped out on her exit interview.

While Reese remains under contract through 2027, when the Sky have a team option, her future, like the franchise’s, is murky.

Season at a glance

• Record: 10-34 (Lottery)
• Offensive rating: 97.0  (12th)
• Defensive rating: 109.9 (13th)
• Net rating: minus-12.8 (12th)

Biggest strength

Offensive rebounding

There were very few things the Sky did well this season, but they were the best offensive rebounding team in the league. The jury is still out on whether Reese and Cardoso can actually play together long-term — they had a minus-9.7 net rating in 528 minutes together this season — but they sure can dominate the offensive glass. Reese led the league with 4.1 offensive rebounds per game, while Cardoso was third at three per game. As a team, the Sky had an offensive rebound rate of 35.5%.

Biggest weakness

Defense

You could have your pick of options here, but we’ll highlight Chicago’s extremely poor defense. Only two teams in the last decade — the 2024 Wings and 2020 Indiana Fever — have posted a worse defensive rating than the Sky did this season (109.9). They forced the fewest turnovers in the league (15.2% opponent turnover rate), gave up the third-most shots in the restricted area per game (20.5) and were tied for the second-worst 3-point defense (36.6% opponent 3-point percentage).

This is going to be a unique free agency period across the league. Every single veteran besides Kalani Brown and Lexie Brown set up their contract to become a free agent this winter in anticipation of a new collective bargaining agreement. The WNBPA and the league are still locked in an intense labor battle, but whenever the new CBA is ratified, it will bring substantial pay raises.

The Sky, like every team, have a number of unrestricted free agents this winter. Atkins stands out as a key priority. She was up-and-down this season, in part due to injuries, but remains an extremely solid two-way guard. After giving up a haul to get her, they have to bring her back.

Vandersloot, a franchise icon, said publicly that she wants to return, and Pagliocca indicated that the team wants to bring her back if she’s healthy. Banham’s shooting will always be valuable and Williams is a reliable back-up big and one of the most well-respected players in the league. Allen and Onyenwere really struggled this season. Could some combination of this group return? Yes, but it doesn’t make sense to re-sign all of them after going 10-34.

The biggest question for the Sky in terms of free agency is whether they’ll be able to convince any stars to come to Chicago. Historically, the organization has not been able to do so outside of Candace Parker, which was a unique situation because she wanted to return home. They are finally set to open their own training facility ahead of the 2026 season — to this point the team has practiced at a rec center — which will definitely help, but the organization still doesn’t have the best reputation.

Until the new CBA is in place and we know the rules for free agency, as well as key numbers such as the 2026 salary cap and the new maximum, minimum and rookie salaries, it’s impossible to make any specific predictions about the Sky’s plans. Plus, they have another important matter to settle before free agency.

The Angel Reese situation

Angel Reese’s sophomore campaign was a roller coaster.

She got off to a historically bad start, but made impressive mid-season improvements to earn her second All-Star appearance in as many years. On June 15th she recorded her first career triple-double, and from June 22 to July 29 she registered 11 consecutive double-doubles to become the only player in WNBA history with multiple double-double streaks of at least 10 games.

After the All-Star break, she was sidelined due to a back injury and missed three weeks. In early September, she gave an interview to the Chicago Tribune in which she aired her frustrations with the front office, coaching staff and roster construction, and called for major moves in free agency. Reese, who also made comments about her teammates, later apologized, both privately and publicly.

The organization eventually suspended Reese for the first half of the team’s game against the Las Vegas Aces on Sept. 7; she had already been suspended by the league for the game on Sept. 5 against the Indiana Fever for accumulating too many technical fouls.

Reese sat out of the second half on Sept. 7 due to a back injury and missed the team’s final two games of the season due to the issue.

The majority of the Sky’s key personnel conducted exit interviews on Sept. 12, the day after their last game. At the time, the Sky said Reese, as well as Atkins and Vandersloot, would hold theirs at a later date. On Sept. 22, the Sky announced that none of the three would do an exit interview after all.

This time a year ago, it seemed Reese and the Sky would have a bright future together. Now, it’s fair to wonder if she’ll even be in Chicago when the 2026 season tips off.

“I am very vocal about what we need and what I want,” Reese said in her interview with the Tribune. “I’d like to be here for my career, but if things don’t pan out, obviously I might have to move in a different direction and do what’s best for me.”

At the time, that seemed to be a nod at potentially leaving in free agency when her contract was up — she’s signed through 2026, and the Sky have a team option for 2027 — but after everything that’s transpired in the last three weeks, it would not be surprising if Reese decides she wants to move in a different direction right now and requests a trade.

Draft outlook

• Lottery selection (via swap with Sun), Nos. 17, 26, 32

The Sky do not control their first-round pick, which they owe to the Lynx. Ahead of the 2024 draft, the Sky traded the No. 8 pick, Sika Koné, a 2025 second-round pick and a 2026 first-round swap to the Lynx to move up to No. 7 so they could select Reese. Then, ahead of the 2025 draft, the Sky cancelled the swap and gave their 2026 first to the Lynx outright in exchange for the No. 11 pick, which they used to select Hailey Van Lith.

The good news for the Sky is that they will still wind up with a lottery pick. The Connecticut Sun owe the Sky swap rights to their first rounder and the Sky also own the Phoenix Mercury’s first rounder, so the Sky will get the more favorable of the Sun/Mercury picks, while the Sun will get the least favorable of those selections. Because the Sun are in the lottery and the Mercury are not, the Sun pick is guaranteed to be better and will go to the Sky.

The 2026 WNBA Draft Lottery has not even been scheduled, let alone completed, so we’ll have to wait to see where the Sky pick in the top-five. We’ll also have to wait to see what happens with the Reese situation and free agency to know their biggest needs. If Reese and Cardoso are both still in town, they will definitely target a guard. Even if they aren’t, a guard is still probably the most likely outcome given this class and the Sky’s desperate need for shot-making and creation.

Here are a few guards that project as potential lottery talents:

• Olivia Miles — G, TCU

Miles would have been the No. 2 pick last year, but decided to forgo the draft and transfer to TCU, where she’ll learn from Mark Campbell — a spread pick-and-roll guru. She is an extremely high-level playmaker and showed off an improved 3-point shot — 40.6% on 5.3 attempts per game — at Notre Dame last season.

• Flau’jae Johnson — G, LSU

Johnson was another player who could have declared for the draft last year, but she decided to return to LSU for her senior season. She has consistently improved throughout her collegiate career and is the type of downhill threat and three-level scorer the Sky need. As a junior, she put up 18.6 points and 2.5 assists per game on 46.8/38.3/81.0 shooting splits.

• Ta’Niya Latson — G, South Carolina

Latson was unbelievable last season for Florida State. She led the country in scoring at 25.2 points per game, and added 4.6 rebounds, 4.6 assists and 2.2 steals. She decided to transfer to South Carolina for her senior campaign and will learn from Dawn Staley while competing for a national championship.

• Azzi Fudd — G, UConn

Fudd, who made her return from a torn ACL last season and was named Final Four Most Outstanding Player after helping UConn win a national championship, also decided to stay in school. The former No. 1 recruit is a lights-out shooter — 43.6% on 5.3 attempts per game last season — but needs to show that she can be a true lead guard and stay healthy.