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The Chicago Sky Taught Me It Was OK To Win Now

Dana Evans #11 of the Chicago Sky reacts against the Washington Mystics at Wintrust Arena on May 26, 2023 in Chicago, Illinois.
Quinn Harris/Getty Images

Many people—I’ll include myself among them—found the Chicago Sky’s offseason strange and shortsighted. They’d been given an opportunity to rebuild after years of contending and a championship win. Their best players had all moved on in free agency, in one terrible farewell-Instagram-post-filled gut punch of an offseason. A strong couple draft classes were on the way. It wasn’t so much an opportunity to rebuild as it was the universe firmly and unmistakably telling them, “You had your fun. Now it is time. Rebuild.” They did not rebuild. Instead, they went about the dreaded “retool.” Coach and general manager James Wade traded the team’s 2024 first-round pick and a 2025 first-round pick swap option to Dallas in a deal to acquire Marina Mabrey, a cool and Defector-certified pure hooper, if not someone you’d ever envision getting that kind of return. The trade said that even with no Candace Parker, even with no Courtney Vandersloot, even with no Allie Quigley, even with no Azurá Stevens, even with no Emma Meesseman, the Sky were still in win-now mode. 

To me, someone whose various long-held WNBA beliefs and gripes are always being proven RIGHT, the offseason made a handy story about the failures of WNBA front offices and the untenable position of the dual coach-GM. No one could do both jobs well, Wade proved. He kept signing away: midrange-pilled Courtney Williams, disgruntled Isabelle Harrison, Australian free agent Alanna Smith. They were no replacements for the departed Hall of Famers, but they were not players one would sign to tank with. When coaches were asked to consider their teams in both the immediate term and the long term—and Wade seemed put in this position by the team's relatively thrifty ownership—they were doomed to fail.

The 2023 Sky, 5-3 on the season, aren't exactly a scary championship contender, but their overtime win Tuesday night against the Indiana Fever was so fun and thrilling that I am now writing about my own belief/gripe being proven WRONG. Wade, one of the best ATO playcallers in the WNBA, drew up the perfect play for two of the team's offseason acquisitions to tie it up at the buzzer and send the game to overtime. It converted me: Winning now is fun! It beats losing now. Now is when we are alive, after all. Now is when we are watching the games.

This moxie-filled .500-ish team is much more compelling than a .200-ish team might be. Kahleah Copper, the lone returning starter from the Sky's title team, continues to dazzle with unlikely cuts and finishes. She's adapted well to being The Gal on her team now; her 27-point performance against the Liberty on Sunday helped the Sky come back from a 17-point halftime deficit to win on the road. The pieces around her are just as fun, and they're a testament to Wade's coaching and scouting chops. Courtney Williams's shot diet was once the basketball equivalent of Jerry Saltz's actual diet, and though it is now slightly healthier—she told reporters Wade banned her from making long twos by painting a second line on the floor of the practice facility—she has retained the clutch gene that made her such a fascinating player to watch in Connecticut. Dana Evans, a 5-foot-6 second-round pick acquired in her rookie season in a different weird Wings-Sky trade two years ago, has blossomed into a do-it-all guard with speed. She put up 20 points off the bench, nine of them in overtime, and if there was ever a case for winning now, just giving your fans something fun and exciting to watch every night, it was the way the crowd in Chicago went crazy for every single thing she did. They built the entire team out of hoopers.

Smith, who scored the game-tying basket at the end of regulation, played garbage-time minutes in the WNBA before finding her footing as a star in Poland this winter. A particular strength of Wade's has been to find valuable players the rest of the league isn't paying attention to—sitting on benches or in leagues overseas. (Rebekah Gardner, his 32-year-old rookie find from last season, will miss time with foot surgery this year.) "It’s been a bit of a rocky road with the WNBA, to be honest," Smith said before the season began. "It’s really taught me to value myself as a player no matter what happens." Her team trusted her with the game on Tuesday night and she delivered. There are always winners waiting for their moments, if only you know where to find them.

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