Chicago Sky’s Challenges Continue as They Miss Playoffs Again

The Chicago Sky won’t be making an appearance in the WNBA playoffs for the third consecutive season. This latest setback was marked by another significant defeat against the Indiana Fever, a team that has dominated the Sky in their last nine meetings. Throughout the last week, the Sky managed a few vital wins in a futile attempt to stave off elimination.

Missing the playoffs once can be seen as unfortunate. Twice is frustrating. The third time signals a clear pattern of mishaps under new leadership. Although six games remain for the Sky, stretching nearly five weeks due to the FIBA World Cup break, the time is ripe for a thorough assessment of yet another unfulfilled season.

General Manager Jeff Pagliocca’s focus has always been on winning. Driven by this, the Sky’s roster underwent major changes in recent offseasons, involving significant trade activity that sacrificed future draft picks. This ‘win now’ mindset is anchored in the belief that Chicago should consistently be a leading contender. Realizing this, however, has proven tough. This season, key acquisitions were the biggest letdowns.

Azurá Stevens, the team’s notable signing at over $1 million annually, struggled, with her points average barely reaching ten due to injuries and personal challenges. Skylar Diggins, crucial to the free-agency period, played only 19 games and critiqued team leadership. She then opted out due to a knee issue. Rickea Jackson’s trade seemed promising, but she suffered a season-ending knee injury after four games. Jacy Sheldon, acquired through a controversial trade involving a first-round pick, lost her starting position.

Despite these setbacks, some positives emerged. Courtney Vandersloot made a commendable comeback, averaging five assists post ACL surgery at 37. Sydney Taylor impressed in her rookie season, delivering key performances with a 14.2 points per game average. Natasha Cloud was occasionally a reliable presence. These positives don’t negate the season’s negatives but provide a fuller picture of the Sky’s journey.

Optimism marked the Sky’s roster foundation. Pagliocca included DiJonai Carrington in the team, knowing she wouldn’t return until after the All-Star break due to injury. He also overlooked the fact that Diggins, Stevens, and Vandersloot were entering the season with injury problems. This mix of factors set the stage for a challenging season. Injuries became a recurring lament without recognizing their preexisting nature.

Beyond injuries, the Sky struggled in close contests, losing 14 of 23 games decided in the final minutes. Their 3-point shooting ranked near the league’s bottom. They grappled with rebounding, allowed too many points in the paint, and didn’t achieve their defensive targets. Head coach Tyler Marsh faced hurdles in crafting a clear team identity for the second year.

Marsh remained hopeful after the pivotal loss to the Fever, expressing optimism for future growth. “We’re not just playing for the right now,” Marsh stated. “We’re playing for the future too.” How much this sentiment applies to the team today remains uncertain.

Most of the roster is contracted through 2027. Only three players — Carrington, Cloud, and Rachel Banham — have expiring contracts. Sydney Taylor is expected back as a free agent with exclusive rights. Yet, Chicago hasn’t maintained a stable system annually, and the current roster status doesn’t promise long-term growth.

Kamilla Cardoso’s and Jackson’s rookie contracts end in 2027. Diggins’ future availability is unclear. Vandersloot, while reliable, is nearing her career’s end. Without a draft lottery pick in 2027, the team lacks depth to build from within or resources for a complete rebuild. After three seasons, the Sky seem entrenched in a cyclical struggle, leaving Pagliocca, Marsh, and ownership in a difficult position.

With little left in the season, leadership must evaluate if a comprehensive reset is necessary after repeated setbacks.