CHICAGO (Feb. 20, 2025) – Chicago Fire FC II today announced that it has signed midfielder Richard “Trip” Fleming III to an MLS NEXT Pro contract through 2026, with a Club option for 2027. Financial terms were not disclosed.
“Trip is one of our former Academy players who played significant minutes with Chicago Fire II before he went off to college,” said Chicago Fire II General Manager Alex Boler. “We have seen how he has grown as a player and as a person at Wisconsin and we know that in our professional environment, he’ll only grow quicker. He’s a blue-collar worker with a high football IQ and it’s always special to have one of our own sign with our Club.”
A native of Boston, Mass., Fleming joined the Chicago Fire Academy during the 2017-18 season, becoming a member of the Fire U-19 team that won the U-19 MLS NEXT Cup in 2021. He then debuted with Chicago Fire II on June 26, 2022, starting and playing the full 90 minutes in a 4-3 victory against New England Revolution II. The midfielder appeared in 21 matches in 2022, starting 19 of them, and added two goals and four assists over 1,746 minutes, best for second-most minutes on the team that year.
“Trip has earned this opportunity after progressing through our Academy, gaining valuable minutes with Chicago Fire FC II, and continuing his development at the University of Wisconsin,” said Chicago Fire FC Sporting Director Gregg Broughton. “This signing reflects our commitment to providing opportunities for Academy players who have proven they are ready for the professional level. We’re proud to see Trip take this next step and look forward to helping him achieve his goals."
Fleming followed up a successful rookie campaign with another sterling season in 2023, featuring in 18 matches and adding two goals and two assists while playing in a variety of positions. His contributions helped Chicago Fire II reach the MLS NEXT Pro Playoffs for the first time.
In the fall of 2023, Fleming headed to the University of Wisconsin-Madison, where he started in all 17 matches he appeared in. He once again featured prominently for the Badgers in his sophomore year, playing over 1,000 minutes and tallying five goals and three assists – including a hat trick in a match against Illinois-Chicago, in which he also assisted Chicago Fire FC forward Dean Boltz.
Transaction: Chicago Fire FC II signs midfielder Richard Fleming III to an MLS NEXT Pro contract through the 2026 season with a Club option for 2027.
Name: Richard Fleming III
Position: Midfielder
Height: 5’8”
Weight: 154 lbs.
Date of Birth: July 7, 2004
Hometown: Libertyville, Ill.
Birthplace: Boston, Mass.
Citizenship: United States of America
College: Wisconsin
