Can the Chicago Sky Rethink Its Strategy To Stay Relevant?

Tic-tac-toe. It’s the first board game a child may learn and, candidly, a rather easy one. Yet professional basketball can often be as simple to understand, once a team has the right players. Consider the Chicago Sky’s winning sequence on their beloved annual kids’ day on Wednesday afternoon. Tic: An inbound to point guard legend Courtney Vandersloot, who dribbled out most of the shot clock. Tac: an incredible pass to Azurá Stevens with the clock nearly expired. Toe: Stevens hit an easy layup for the clinching points.

And yet, when one looks beyond the cheerleaders’ signs, one finds that running the organization is not so simple. What three steps can, no, must Chicago take to place its winning pieces in the board’s overpowered corners?

1. Timeout, Jeff!

Before the Sky can become a long-term, successful franchise, it must find a way to retain its best talent. Too many superstars, starting with an unhappy Sylvia Fowles (traded to already-dominant Minnesota for the modestly talented Erika de Souza), left with their best years still ahead. After the departures of future Hall of Famer Elena Delle Donne and the entire core of the 2021 championship team, it was undeniable that Chicago had a brawn drain.

Part of the issue was the presumably cost-conscious choice to give James Wade both coaching and general manager duties. Wade was an excellent coach, but his decision to trade a mountain of assets for Marina Mabrey, only for Mabrey to depart for a token return, puzzles. (To make the trades worse in hindsight, Mabrey developed into one of the league’s best players.)

After the 2023 season, Chicago made an intelligent choice to name a separate GM, Jeff Pagliocca. Pagliocca’s choices, however, leave current fans befuddled. Too often, he traded a star player for draft picks, only to use those picks to acquire underwhelming talent or, worse, let a popular player depart (See: Angel Reese).

Our site understands that teams must sometimes rebuild, but not every other year! Pagliocca would do better to show patience with a developing team rather than repeatedly recycling shooting stars back through the ozone.

2. Facilities

In July 2024, the Sky announced plans to build a much-needed practice facility. What happiness! When this reporter asked Wade about the plans, he expressed optimism that team investments would boost the franchise.

Unfortunately, cost overruns (welcome to America) occurred, and the building is unfinished. Credit Sky PR for a clever halftime bit featuring current coach Tyler Marsh and Pagliocca, who wear yellow vests and demonstrate the facility’s upcoming promise. The Chicago Sun-Times, often critical of the Sky to a fault, nonetheless is correct in expressing frustration with the delay.

The Sky, to be diplomatic, may be faultless in the agonizing wait for infrastructure improvement. It is fair to criticize, however, broken promises spoken without a full context. To reiterate: Team NBS Media understands. Building anything can be complicated and expensive. However, it would help free agents and current players to have more transparency regarding these improvement measures.

3. Don’t Give Up, Chicago!

The Sky isn’t selling off the baskets just yet, nor should they! It is disappointing that no Chicago player made the city’s All-Star game. However, the team’s upcoming events at the new Obama Presidential Center are fabulous uses of the city’s resources.

And, lastly, consider the legacy of the second Sky player to have her number retired: Candace Parker. Parker, true, moved on for greater success in Las Vegas. However, the gesture to hoist her #3 into the Wintrust Arena rafters was more than a footnote. To this scribe, it was a celebration of what the Sky were in their championship season. The team offered a return home for a native legend and a haven for her escape from a challenging situation.

Chicago, the city of two three-peats in men’s basketball, can certainly offer success for a women’s hoops organization. It will take strong inbounding with draft picks, passes through a new building, and a layup before fan patience sounds the final alarm. Yet, once these three pieces are placed, the long-hollaring skeptics of Sky basketball will only examine their board in regret.

While foes try for victory downtown, the Sky will soon race around the WNBA’s winning corners, securing the entire city’s adoration for winning basketball in the new millennium.