Only four players from the Chicago Sky’s 2025 rotation remain as the franchise enters the 2026 WNBA season. It was indeed a complete overhaul, one that featured the offseason’s most notable move: Angel Reese’s trade to Atlanta.
In return, the Chicago Sky brought in veterans Skylar Diggins, Azurá Stevens, and Natasha Cloud, who GM Jeff Pagliocca described as “certified winners.” As it appears, the franchise is switching to a veteran-heavy lineup and strategy. And fair enough, it seems about time they try something new after three straight losing seasons.
The question now is whether these radical changes will finally push them back into a playoff run, or if this is simply another transition season for the franchise.
The End of the Angel Reese Era
Angel Reese, who the Chicago Sky drafted as the 7th overall pick in 2024, was the face of the franchise during the two seasons she spent with the team. And on a personal level, Reese enjoyed a very good spell in Chicago. She led the WNBA in rebounds per game in both seasons she played with the Sky. She was also a WNBA All-Star in both years and currently holds the league’s single-season record for total rebounds.
Sadly, all those records and accolades, however impressive they sounded, did not translate into good results for the team. The Sky finished with a 13–27 record in 2024 and followed that with a disappointing 10-34 campaign in 2025. They also missed the playoffs in both seasons. And those poor results were indeed tied to Reese leaving. She reportedly felt she deserved a better team, publicly criticized the franchise, and was even sanctioned by the organization for her actions.
In short, the Angel Reese era was tumultuous to say the least. And to “achieve roster balance,” as the Chicago Sky put it, they ultimately decided to let her go. Of course, despite the off-court tensions, losing a player like Reese still meant losing a high-quality talent. And even beyond basketball, it also meant losing a marketing goldmine and all the attention she brought to the franchise. In fact, the trade received quite a backlash from fans, with thousands reportedly unfollowing the Sky’s social media accounts after Reese departed.
Heading into the 2026 season, the Chicago Sky must now prove that they made the right decision. They face the challenge of winning back a fanbase that felt “betrayed” by the move, as evidenced by “Free Angel” and “Fire Jeff” shirts appearing at preseason games. They simply cannot afford another subpar season. The expectation is now clear: this is a win-now situation for Chicago.
Skylar Diggins Changes the Timeline
Before the massive offseason overhaul, the Chicago Sky appeared to be building around a young rookie core anchored by Angel Reese and Kamilla Cardoso. But by signing a seven-time All-Star and 14-year veteran in Skylar Diggins to a two-year deal, the franchise has made it unmistakably clear that they are no longer in the business of growing pains. Their direction has now shifted from a long-term rebuild to an immediate, urgent pursuit of playoff contention.
And Diggins is far from the only piece of that pivot. The Sky have added Natasha Cloud, a 10-year veteran. Azurá Stevens brings the credibility of a WNBA championship ring, having won it all in 2021. And DiJonai Carrington, now entering her sixth WNBA season, adds another layer of proven professional experience to the Sky roster. GM Jeff Pagliocca was characteristically direct in articulating the vision behind these moves. “What ‘winning now’ means is getting ultra-competitive players here who won’t live with anything less than success,” he said.
And this core of veterans, Diggins chief among them, is already leaving its mark on the organization’s culture. Diggins has embraced the leadership role with so much conviction that she has now established herself as a vocal extension of the coaching staff. She has described her leadership style as “not easy, but good” and hinted that, once the regular season begins in earnest, the intensity she brings may increase further.
For a roster featuring 13 players with two years or fewer of professional experience, that kind of demanding, uncompromising presence appears essential. As Sky forward Rickea Jackson put it, “When you walk in a room, you feel her aura, you feel her energy. She’s not afraid to let it be known. Learning with Skylar, building with her, has been fun so far.”
The Hailey Van Lith Gamble
The decision to waive Hailey Van Lith, just one year after selecting her with the No. 11 overall pick, was perhaps the clearest sign yet that the Chicago Sky was fully committing to their new “win now” approach. In fact, within just a few weeks, the Chicago Sky has now effectively moved on from every first-round pick from its last two draft classes. In many ways, that further reinforces the franchise’s complete end to its “build with youth” approach and the beginning of an all-in veteran era.
Fans’ reaction to this approach, especially to Van Lith’s waiver, has, however, been far from pleasant. Many fans criticized the franchise online, arguing that Van Lith deserved more than just one season, especially after showing signs of growth during the preseason. Hailey Van Lith did actually impress during the 2026 preseason, averaging 12.5 points and 4.5 assists. But according to reports, the coaching staff still does not view her as the ideal fit.
The preference, as it appears, was for experienced guards. Specifically, Chicago reportedly waived Van Lith to clear both roster and cap space for Natasha Cloud, a three-time All-Defensive Team selection. In the words of general manager Jeff Pagliocca, “Natasha is one of the best passers and defenders in our league. She fits in with the other proven winners on our roster.”
But to be fair, the decision to waive Van Lith was not solely based on preseason form. Van Lith’s rookie season in 2025 was difficult overall. She averaged just 3.5 points per game while shooting 16.1% from three-point range. She also dealt with nagging ankle injuries throughout the year. But while her preseason performance did not impress the Chicago Sky, she seemed to have convinced the Connecticut Suns with it, as they claimed her off waivers two days after Chicago let her go.
Right now, the Hailey Van Lith decision feels like such a major gamble. If the Sky return to the playoffs and contend immediately, the front office will likely be praised for making difficult but necessary decisions. But if the team struggles again, moving on from multiple young prospects and marketable players could be one of the biggest failures of this new regime.
Kamilla Cardoso’s Franchise Leap
Kamilla Cardoso, entering her third WNBA season, is one of the Sky’s young core who will occupy the center stage in this new project. Trading Angel Reese out has automatically elevated her to the undisputed center stage of the Sky’s long-term vision. And the expectation for her now is to start taking responsibility. As she said in an interview: “My teammates and coaches are always telling me how much they trust me and believe in me. So I think, I have also to start believing in myself and just go out there and do whatever my teammates need me to do in order to win games.”
Kamilla Cardoso has indeed shown consistent improvement over her first two seasons. In her rookie year, which was hampered by injury, she averaged 9.8 points, 7.9 rebounds, and 1.4 blocks per game. In 2025, she raised her numbers slightly, averaging 13.6 points, 8.5 rebounds, and 2.5 assists per game. Now, the expectation is that she takes up a notch again, especially now that she’ll have even more prominence with Reese gone.
And ultimately, her performance this season might end up being a major determining factor in how successful the Chicago Sky season turns out to be. She will have established veterans like Natasha Cloud and Courtney Vandersloot feeding her. And with that support, if she eventually has an All-WNBA caliber center performance, the Sky could legitimately compete for a high playoff seed in 2026, or even go on a bit of a playoff run.
Biggest Strengths and Lingering Concerns
There are a whole lot of advantages that come with having the kind of experience that the Chicago Sky have assembled. Their biggest strength is undoubtedly veteran leadership.
Also, with Skylar Diggins, Natasha Cloud, and Courtney Vandersloot running the backcourt, Chicago now has elite playmaking and experience. They also possess tremendous size and defensive potential, which is led by the 6-foot-7 Kamilla Cardoso and the versatile Azurá Stevens. Also, with defenders like DiJonai Carrington, Chicago could become one of the league’s toughest defensive teams.
However, amidst all these advantages, there are legitimate concerns surrounding this roster. The team is now made up of players who will be playing together for the first time. So, developing team chemistry remains a major question. The roster balance is also somewhat uneven, with heavy guard depth but limited frontcourt options behind Cardoso and Stevens.
And offensively, the Sky still have plenty to prove. They struggled heavily from three-point range in 2025, and without Angel Reese generating second-chance opportunities, they must now show that they can consistently create efficient offense within this new system.
Season Prediction: Playoff Push or Another Transition Year?
With the approach they have taken to building their roster, the Chicago Sky are definitely entering the 2026 season hoping to fast-track their rebuild rather than endure another lengthy transition year. As Jeff Pagliocca has said, it’s about winning now.
However, the Chicago Sky seems to be one of the league’s most unpredictable “wild card” teams entering the 2026 season. Analysts are split on whether their aggressive offseason will translate into a deep playoff push or into another transition year, especially given the heavy roster turnover.
Most projections, however, place them around the playoff bubble, with expectations ranging between 9th and 11th in the standings. However, not qualifying for the playoffs this season will indeed be a failure for the sky. But ultimately, if players like Kamilla Cardoso can take another leap and the veterans click early, the Sky could accelerate their rebuild faster than expected and sneak into the postseason.
