The “heartbreaking endings to 2026 Chicago Sky games” montage that CBS showed in the final minute of the Sky’s Saturday matinee against the Las Vegas Aces hinted at how this game might unfold. One of the endings was from a game against the New York Liberty in late June, the same game 25-year-old undrafted rookie Sydney Taylor debuted in Chicago’s starting lineup. On the possession after Taylor hit a go-ahead three with 15 seconds left, the Sky let Sabrina Ionescu waltz to the rim for a layup to give New York the lead back, and Taylor’s next shot at the buzzer fell short. Her teammates had to peel her off the floor, where she sat in tears. Team minority owner Dwyane Wade, sitting courtside, came over and leaned down to pat her shoulder. Taylor called it a “tough feeling” after that game. “But if you’re willing to take those shots, you’ve got to be willing to live with the result.”

Fifteen games later, Taylor is the number-one option still taking those shots, and Saturday’s was a happier result to live with. A’ja Wilson’s much-too-easy go-ahead layup with three seconds left seemed destined for the Sky heartbreak montage. But on the next play, Taylor shook off Jackie Young (with the help of another screen from Elizabeth Williams) and hit the game-winning three.

“That New York game has been on repeat for me since it happened, so I was really due for one,” Taylor told reporters postgame.

The words “pleasant surprise” or “sports fairytale” do not feature in writing about the Sky very often, but Taylor’s rookie season demands them. She played her first four years of college basketball at UMass before transferring to spend her final year of eligibility at Louisville, a pretty pedestrian season that left her basically a non-prospect in 2024. When the Sky invited her to training camp this spring, Taylor had been grinding for two years in Lithuania and Poland. A trio of loud preseason performances won her a spot in a crowded guard group—so crowded, in fact, that another Louisville product, Hailey Van Lith, was cut to make room.

Rickea Jackson’s early-season ACL tear meant there were suddenly lots of shots available for other Sky players to take. It also exposed some issues with the Sky roster: Taylor has turned out to be the only one who can create those shots for herself at high volume. In her arsenal are a quick release, enough speed to attack the rim, and a pretty floater. She’s averaging 18.4 points per game since she joined the starting lineup in mid-June, a promotion she earned right after a 30-point game against the Indiana Fever.

Saturday’s ending, a rare one-score win for the Sky, also offered some clues as to how the Sky have been losing so many of these tight games. The veteran point guard Natasha Cloud, in her euphoria, didn’t realize there was still time on the clock, and Taylor had to quickly extricate herself from Cloud’s hug to be ready for the Aces’ last shot. In a different game blown to the Liberty, in late July, Taylor could be heard screaming “DON’T FOUL!” half a second before Azurá Stevens … fouled Ionescu on a drive that would be the game-tying and-one. Taylor’s 31-point performance that night was all for naught.

Beyond giving an 11-18 team something to root for and distracting from the Sky’s unresolved Instagram-aired disgruntlement issue, Taylor’s story is encouraging for another reason. Former head coach and general manager James Wade had a real knack for pro scouting, but in the three years that current GM Jeff Pagliocca has run the team, that area hadn’t seemed like much of an organizational strength. The Sky’s money and facilities troubles put them at a disadvantage with elite free agents, and while there is one obvious means around that problem—getting franchise-changing talent in the WNBA draft—Pagliocca has shown little interest in it, choosing instead to hand Sonia Citron and Olivia Miles to other teams. (The Sky also don’t own the rights to their first-round pick in 2027 or 2028.) A less obvious means around that problem is to hit on gems like Taylor with some consistency. They gave her a shot, and now they’re reaping the results.