Winn was the second-round draft pick of the Cardinals in the 2020 MLB Draft out of Kingswood High School in Kingswood, Tx. He has a bat with opposite field power and a cannon for an arm that topped 100 mph during a play from shortstop to first base in the Futures Game during All-Star Game weekend in 2022.
Winn significantly improved at the plate and basepath during the 2022 season, seeing time in Peoria and Springfield. MLBPipeline.com said Winn became a more patient hitter during 2022 and started elevating the ball more. This led to a jump in home runs and extra-base hits.
MLB Pipeline.com said, "He may not be more than an average hitter in the end who just pushes past double-digit dingers in the bigs, but given the impact, he can have on the basepaths, and in the field, that would still be enough to make Winn an impact Major League shortstop."
While the Cardinals have a shortstop in Tommy Edman and backup from Paul DeJong, Winn will be given plenty of opportunity to impress this spring while Edman plays for Team Korea in the WBC. Winn will likely continue to develop at either Springfield or Memphis, with the possibility of making his debut with St. Louis late in the season.