Fired-Up Skylar Diggins Calls Out ‘Loser Mentality’ After Chicago Sky’s Slump—Is a Major Shake-Up Coming?

All-Star guard Skylar Diggins is turning her offseason gamble into an early-season jackpot for the Chicago Sky. Since inking a free-agent deal with the club in April, the 33-year-old has reignited one of the league’s most dynamic backcourts, flashing the same downhill speed and crafty footwork that made her a six-time All-WNBA pick in Phoenix and Dallas. In Chicago’s Commissioner’s Cup win over Connecticut, Diggins poured in 24 points—16 of them in a blistering second quarter—while slicing through double-teams, finishing with either hand and icing the game from the stripe. The performance pushed her season scoring average to 19.6 points and underscored why head coach Teresa Weatherspoon has given the veteran the keys to a free-flowing, guard-centric offense. The night also carried historical weight: with her fifth free throw, Diggins passed Cappie Pondexter to move into 10th place on the WNBA’s all-time list, an achievement she celebrated with a fist pump and a quick nod to Chicago fans inside Wintrust Arena. “I’ve studied the great scorers in this league for a decade,” she said post-game. “To see my name next to theirs means the work is paying off—but we’ve got bigger goals.” Those goals include chasing the franchise’s first title since 2021, and early returns are promising. Diggins is top-five league-wide in usage rate and assist-to-turnover ratio, balancing her downhill aggression with timely kick-outs to sharpshooters Diamond DeShields and Marina Mabrey. Her partnership with center Elizabeth Williams has also turbo-charged Chicago’s pick-and-roll game, drawing extra defenders and freeing the Sky’s forwards for clean looks at the rim. Off the floor, Diggins has leaned into Chicago’s community initiatives, hosting a youth skills clinic on the South Side and launching a mental-health roundtable for young athletes. The outreach mirrors her on-court leadership; teammates say her voice in the huddle is as valuable as her left-handed scoop layup. Next up: a two-game road swing through Seattle and Las Vegas—both pace-and-space offenses that will test Chicago’s perimeter defense. Diggins welcomes the challenge. “I feel fresh, my legs feel great, and I’m finally healthy,” she said. “When I’m healthy, I’m dangerous—and so is this team.” Search volume around her name is spiking for good reason: whether she’s crossing over defenders, climbing the record books or amplifying women’s sports in Chicago, Skylar Diggins is once again must-watch basketball in the Windy City.