[2][3][4] At Pekin High School ('16) in Jefferson County, Iowa, Winn was a two-time All-State wide receiver/tight end in football.
He was also a two-time all-conference first team basketball player (setting the school's all-time single-game rebound record, with 26 in 2014), and a 4 × 200 meters relay 2015 state champion in track.
During his two years playing for the Reivers, he was 9–2 with five saves and a 2.37 ERA in 31 games (7 starts), pitching 87.1 innings with 115 strikeouts.
[18] Winn was selected by the San Francisco Giants in the 20th round of the 2017 MLB draft, but he decided to return to Iowa Western for one more season.
[21] In 2022, returning to pitching midway through the season after nearly three years away from the game, he played for the Single-A San Jose Giants, the High-A Eugene Emeralds, and the Double-A Richmond Flying Squirrels.
[25][27][10][29] Winn made his MLB debut on June 13, against the St. Louis Cardinals, and in four innings gave up one run on one hit while walking three batters and striking out two.
"[29] Winn made 9 appearances (5 starts) during his rookie campaign, logging a 1–3 record and 4.68 ERA with 35 strikeouts and one save across 42+1⁄3 innings pitched.
Winn began the 2024 season out of San Francisco's rotation, compiling a 3–8 record and 7.16 ERA with 48 strikeouts over 12 starts.