After a turbulent and ultimately disappointing 2025 WNBA season, the Chicago Sky find themselves at a crossroads. With their elimination from playoff contention, it’s clear the franchise is deep in the early stages of a rebuild. But despite the postseason being out of reach, opportunities remain for the front office to not just evaluate talent but to recalibrate the direction of the team after staying put at this year's WNBA trade deadline.
Anchored by breakout stars Angel Reese and Kamilla Cardoso, the Sky possess a promising young frontcourt duo with the potential to shape the future of the league. However, questions regarding coaching leadership, guard play, offensive identity, and veteran presence plague the franchise ahead of the long offseason.
With the 2025 WNBA trade deadline firmly in the rearview mirror, the Sky must now turn inward and deliberately form a forward-thinking roster using the best organizational decisions to set the foundation for future success. Whether through player releases, benchings, lineup experimentation, or strategic signings, Chicago has a vital opportunity to reshape its identity and begin building a sustainable contender from the ground up. Let's see which steps will help the Sky get there the fastest.
1. Target veterans to mentor the young core
Post-deadline is critical for even non-contending teams. The Sky could proactively add a high-scoring, floor-spacing veteran who can guide their young nucleus, especially since they lost that benefit after bringing in Courtney Vandersloot during last offseason due to her season-ending ACL injury.
A proven scorer whose team may try to get value before free agency would add elite playmaking and leadership, potentially accelerating the development of Reese and Cardoso while keeping Chicago competitive in the near term. Losing out on a few draft picks would be worth it for at least one player who could act as both a mentor and key contributor.
2. Focus on internal development
With the roster still in flux, continuing to evaluate and promote internal talent is essential. Elizabeth Williams has become a force, earning more starts, logging double‑doubles, and helping pace the Sky in rebounding. Chicago should make her a consistent part of the starting rotation as a reward for her efforts and give her more responsibilities on both ends of the floor.
Similarly, Michaela Onyenwere has demonstrated scoring potential, averaging in double figures last season and earning more starts this year. Committing to her development as a starter too could add reliable spacing and scoring around Reese and Cardoso.
Meanwhile, rookie Hailey Van Lith has seen limited playing time, averaging just 12.4 minutes a game in the W after logging 30 in her junior and senior years at TCU. She could make a significant impact on the young rebuilding squad, especially after all the hype surrounding Van Lith's reunion with former LSU teammate Reese, but the coaching and front office staff have to assess whether they want to give her more developmental minutes.
Otherwise, the clear choice would be to explore trading her if she doesn’t fit the system long‑term and a better fit is available. And if Van Lith doesn’t fit, the Sky could pivot to relying on a more established guard with upside like Vandersloot, if she's able to recover well enough from her injury in time for the 2026 campaign.
Paying attention to these internal moves will not only inject energy but also help evaluate which players can anchor the roster moving forward.
3. Define roles around Angel Reese and Kamilla Cardoso
Two-time All Star Reese and All-Rookie Cardoso form the franchise’s young core known affectionately as the “Skyscrapers.” With only they and a few rookies under contract beyond 2025, it's time to tailor the team identity around them. The Sky need to clearly define on-court roles and decide which players will fit into them.
Reese will slot in as the physical, aggressive interior centerpiece, Cardoso will act as the versatile frontcourt extension, and floor-spacing wings and savvy guards will be surrounding them, if all goes according to Chicago's plan. A supporting cast that complements the duo's strengths, minimizes overlap, is the most important factor.
4. Reinforce perimeter shooting and playmaking
To say Chicago’s offense has struggled would be an understatement. The Sky are leading the league in turnovers and lack consistent three-point threats. Onyenwere is one of the few above‑35% three-point shooters in Chicago, so it would be a smart idea for the Sky to re-sign her and continue adding more three‑point shooters in the offseason. To really take advantage of this skillset, they should watch out for available guards or wings who can stretch the floor and create space for their bigs.
5. Evaluate whether coaching dynamics are the correct fit
Head coach Tyler Marsh is now the face of the rebuild, and while the front office and built roster bears most responsibility, leadership and discipline will matter moving ahead. The Sky have assembled a strong staff, including Tanisha Wright, Courtney Paris, Rena Wakama, Aaron Johnson, and others, and the franchise shouldn't hesitate to reconsider those decisions during its rebuild too. Whether Marsh and his crew are the right ones to lead this team into a competitive near-future is just as crucial to question as the fit of each player.
6. Use remainder of 2025 season for evaluation
With the season lost, the Sky should pivot to using remaining games as real-time auditions. The last few contests can provide clarity for 2026 decisions involving player contracts, rotation roles, and free-agent strategy.
Everyone from rookies like Maddy Westbeld and Van Lith to veterans like Onyenwere and Williams should all be evaluated thoroughly. The goal is t identify who deserves long-term roles with the new-look Sky and who does not.
Chicago’s campaign may be over, but the team's reconstruction journey is just beginning. With a misfiring offense, rampant injuries, and a rocky deadline experience, it’s time for a full reset. The moves explored — balancing roster changes, developmental clarity, veteran mentorship, and front-office discipline — are designed to not just solve the current season's problems but to accelerate the team's transformation into a sustained playoff contender centered around Reese, Cardoso, and the evolving young backcourt.
This plan demands tough personnel decisions and smart long-term vision, but it is absolutely the kind of foundational work the Sky must do now to ensure that their rebuild is more than just a reset and becomes a resurgence.
