[1] As a junior in 2017 he was 9–0 with a 0.73 ERA with 95 strikeouts in 47+2⁄3 innings, along with batting .388 with two home runs and 19 RBIs, earning himself the title of Colorado's Gatorade Baseball Player of the Year.

The "de-load" program, as the organization calls it, emphasizes building a foundation mentally and physically, while resting bodies from a strenuous senior season and pre-draft showcase circuit.

The players are put through a strength program and classroom work until post-season fall instructional training starts.

[15] Winn made his professional debut in 2019 when was assigned to the Hickory Crawdads of the Single–A South Atlantic League with whom he started 18 games, compiling a 4–4 record with a 4.46 ERA over 68+2⁄3 innings.

[22] After the end of Frisco's season in mid-September, he was promoted to the Round Rock Express of the Triple-A West where he posted a 3.38 ERA over two outings.

[31][32] Following that season, he played for the Criollos de Caguas of the Puerto Rican Winter League, going 2–0 with a 2.63 ERA and 24 strikeouts over 24 innings.