Draft Capital and Trust in Teresa Weatherspoon Set To Guide Chicago Sky Rebuilding Season » Winsidr

There are a lot of paths a rebuilding team can take in professional sports. None are digestible. 

They often involve trading away major pieces of their club, playing games with the secret intent of losing  in order to boost draft positioning, or turning the page on one or more members of their coaching or front office staff. 

The Chicago Sky look to dabble in all of these options as they work to come back from a strange 2023 season. The season was headlined by former head coach and general manager James Wade leaving the team for a job with the Toronto Raptors, just one year removed from winning WNBA Executive of the Year honors. 

The Sky have a few avenues to look down to try and find themselves in a position to hoist  a trophy in September. Between the draft capital they’ve gotten back after Wade traded five of their lucrative picks away for Marina Mabrey, and their hiring of a WNBA legend and seasoned coach in Teresa Weatherspoon, it feels like the Chicago Sky  will have a good start to what has ended up being an abrupt rebuild. 

This is part one of a three-part series on the “Rebuilders” in the WNBA for the 2024 season—the moves they have made and how quickly they can hit the ground running.

Draft: Back to Square One

One of Wade’s most head scratching decisions as an executive with the Sky was trading away the team’s 2024 first round pick and 2025 first round pick swap with the Dallas Wings in exchange for Marina Mabrey back in February 2023. It was a huge haul, and one that came amidst major uncertainty for the direction of the squad moving forward without Candace Parker, Courtney Vandersloot or Stef Dolson. This is no knock on Mabrey, who emerged as a top scoring option for the Sky in 2023 and was a delight to watch glide up and down the floor for Chicago. But the loss of these picks became a huge blemish on the team’s record as soon as Wade headed north of the border for NBA pastures. Suddenly, the direction he had envisioned for the team’s retooling, and not a needed rebuilding, was murky. 

The front office, newly headed by GM Jeff Pagliocca, made moves to finally cement a true rebuild for the club. They traded away the face of the franchise, Kahleah Copper, to the Phoenix Mercury to regain ground in the draft. They also traded Morgan Bertsch in addition to Copper, securing the third overall pick in the 2024 WNBA draft, and several future picks. The Sky also captured the eighth overall pick from a fellow rebuilding team, the Los Angeles Sparks, in exchange for Julie Allemand, the rights to Li Yueru, and Chicago’s 2025 third round pick. 

The Sky, with just two transactions, managed to get back the third and eighth picks in the 2024 draft. Prior to drafting at eight, they then swapped picks with the Minnesota Lynx and moved up to seventh.  This ensured Chicago  could take both Kamilla Cardoso and Angel Reese with the third and seventh picks respectively. In addition, they also took Brynna Maxwell with their 13th pick, a shooter who said in her introductory press conference she can bring a new element to this Sky team. 

“We’re the underdogs in this league, but I think we’re going to kind of surprise a few people if we put it all together,” Maxwell said. 

Reese added that while she and her fellow draftees in Cardoso and Maxwell are going to come in and represent the franchise well as a potential new young core, it cannot be forgotten what the team did before them and in recent memory. 

“The last championship was in 2021…being able to bring that back here is something I’m looking forward to,” Reese said “We have a lot of players on the team that have won. So being able to come in and just have that winning mindset, and going to a team where everybody around you just wants to do whatever it takes to win? It’s fun to play with players like that.”

While it’s always unfortunate to see the end to a contending era, which has been especially marked by the trading of Copper, one thing this team can control, especially as they look to attract and retain talent like Cardoso, Reese, or Maxwell, is how they present themselves as a premiere destination. 

During the introductory pressers for Reese and Maxwell, Chicago Sun-Times reporter Annie Costabile posted a short clip of Reese walking into the conference in what looked like a high school gym, with little fanfare and an awkwardly placed backdrop and podium in  the middle of the gym. Compare this welcoming to that of Alissa Pili’s in Minnesota where the community and front office lined up to applaud her entrance at Target Center, and had members of the Indigenous and Samoan communities make her feel right at home Or like  the Seattle Storm who recently constructed a brand new, state of the art practice facility, and the Phoenix Mercury who also has a  new facility It’s sad. 

Twitter was ablaze with reactions to this clip of Reese’s welcome Users  called out part-owner Dwyane Wade to invest more in the team, and wondered if the Sky’s 2021 championship should be cherished even more considering that Candace Parker and Kahleah Copper had even less to work with. 

This is a controllable factor, and one that the Sky’s ownership really need to face up to if they want to attract new talent and fans in 2024 and beyond. Costabile mentions in her piece that the team has been “touting” new plans for a practice facility, but have yet to present anything concrete. Hopefully, once this ball starts rolling, the genuine feeling of a rebuild will be felt amongst the organization and its fans. 

Current Roster: Leaning Into Youth Movement

As with any proper rebuild, growing pains and leaning into a club’s youth are key to coming through the other side as a better team than where it was left at the start of the revamp. This is where players like Elizabeth Williams, Dana Evans, Izzy Harrison, and Marina Mabrey will become extremely important. All have been a part of the Sky system since last season and will now have to put on a leadership hat to try and right the ship for Chicago. They will see how they will mesh on the floor together without Copper or Courtney Williams, who left for the Minnesota Lynx this free agency. 

The Sky signed Diamond DeShields this offseason as well, presumably as a means of adding guard depth after losing Williams. DeShields, along with the rest of the remaining Sky players, form a solid core to support Reese, Cardoso, and Maxwell, who may need some time adjusting to WNBA speed and physicality. While the Sky lost big pieces in Copper and Williams, they have a competitive group still left that will grow together under the tutelage of Weatherspoon. Look for center Elizabeth Williams to especially step up after a big year defensively, and for Evans to build on her Sixth Player of the Year campaign from last season with a more defined role in 2024. 

Front Office and Coaching: Experience Rewarded

To set the tone for the rest of the season, Chicago separated the dual general manager and head coaching position. This has helped usher in a new way of doing business for the Sky, allowing Pagliocca (a former development coach with the squad) and Weatherspoon (a New York Liberty Ring of Honor member, five-time All-Star, and former New Orleans Pelicans assistant coach to focus on their respective crafts.

In the Sky’s new-hire press release, Pagliocca said that he is “eager to build upon our tradition of excellence, hard work, and winning, in this energizing new chapter of Sky basketball.”

“Expect us to bring unmatched toughness, grit, and relentless competitive spirit to Chicago,” he added. 

Grit is in Weatherspoon’s DNA, making the pairing of these two ideal for a Chicago rebuild. Weatherspoon, the first player to win the league’s Defensive Player of the Year award, intends to further a  winning culture in Wintrust Arena. She oozed with excitement in her  introductory press conference about taking on the challenge of leading this new look Sky team, similar to Pagliocca’s passion displayed. 

Chicago’s moves signal to anyone paying attention that yes, the team had to and has taken the steps to correct the mistakes made by past leadership. The Sky now have a better chance, thanks to  the draft especially, to make a significant  leap from a deprived  franchise to possibly playing spoiler for several teams come playoff time.