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Trip Fleming III signs with Chicago Fire II

Alex Calabrese

20 Feb 2025 — 2 min read

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The Chicago Fire have signed Trip Fleming III to an MLS Next Pro contract, the club announced this afternoon. Fleming recently completed his second full NCAA season at the University of Wisconsin.

Fleming, 20, is a graduate of the Fire’s academy and previously played for Chicago Fire II in 2022 and 2023. Across those two seasons, the central midfielder played in 39 league matches and scored four times.

Since starting life at Wisconsin in late 2023, Fleming established himself as one of the school’s top players. In his freshman season in 2023, he was the only non-keeper to start all 17 games, seeing nearly 1,500 minutes of action. The Libertyville native appeared 13 times in 2024 and discovered a scoring touch, scoring five times, including a hat trick against UIC. He also added three assists.

trip fleming iii — (via Barbara Calabrese)

Fleming will be one of four Wisconsin Badgers at the Fire’s Endeavor Health Performance Center this season. First teamers Chris Mueller and Tom Barlow previously played college soccer in Madison, while 2025 SuperDraft selection Dean Boltz was a teammate of Fleming last year. Fleming’s new Fire II teammate, 17-year-old goalkeeper Patryk Stechnij, is committed to playing soccer at Madison as well and is set to move there in the summer.

Interestingly, Fleming is also not the first academy graduate the Fire have brought home after a spell in college. 18-year-old Dylan Borso was signed to a homegrown contract in December after a breakout ACC season at Wake Forest, where he led the Demon Deacons to a conference title. However, Fleming is the first-ever player to leave college early to return to Fire II as a former academy player in Chicago.

Ultimately, Fleming is the next up in a line of truly intriguing Fire II signings this offseason that should help make the team a contender in MLS Next Pro under new head coach Mike Matkovich. The second team has already added UNC’s Sam Williams, Syracuse’s Olu Oyegunle, and Cittadella’s Claudio Cassano in a trio of outside-the-box moves, and there are more signings on the way that haven’t yet been announced.

https://meninred97.com/fire-draft-pick-dean-boltz-wants-to-be-a-hometown-hero/

https://meninred97.com/sources-chicago-fire-ii-sign-olu-oyegunle/

https://meninred97.com/sources-fire-ii-finalizing-claudio-cassano-deal/

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