CHICAGO (Aug. 9, 2025) – Chicago Fire FC today announced that the Club has signed Chicago Fire FC II midfielder Richard “Trip” Fleming III to a short-term agreement. Fleming will be available for today’s Chicago Fire FC home match against Los Angeles Football Club at SeatGeek Stadium in Bridgeview, Ill.
Kickoff against LAFC is scheduled for 7:30 p.m. CT and the match will be broadcast globally on MLS Season Pass on Apple TV, and transmitted locally WLS 890 AM on wlsam.com (English), and Que Buena 105.1 via the Uforia app (Spanish).
Fleming, 21, signed with Chicago Fire II in February after spending two seasons at the University of Wisconsin-Madison. Prior to playing college soccer, Fleming was a member of the Chicago Fire Academy from 2017 until the Fall of 2023. The midfielder was a member of the Chicago Fire Academy U-19 side that won the U-19 MLS NEXT Cup in 2021 and he made his Chicago Fire II debut on March 26, 2022 against Orlando City B.
Most recently, Fleming scored a brace on Aug. 4 that helped the team earn a 6-1 win against Columbus Crew 2 at SeatGeek Stadium. He has been an integral part of the Chicago Fire II squad that was named MLS NEXT Pro Team of the Month for the month of July after consecutive Team of the Matchweek performances for Matchweek 20 and 21.
Fleming has played 17 matches (16 starts) so far in the 2025 MLS NEXT Pro season, tallying a career-high seven goals and registering two assists and a 90 percent pass completion rate so far this season. He has played in 55 matches and registered 4,651 minutes so far over the course of three seasons.
It is the first short-term agreement for Fleming. Per MLS rules, a Club may sign a player from its affiliate (MLS NEXT Pro or USL) to a maximum of four Short-Term Agreements (up to four-day contracts) each season (maximum of 16 days). An individual player may be included on up to four MLS regular season match rosters each season. However, that player may appear in no more than two MLS regular season matches. An individual player may appear in any number of non-league games during the terms of his four Short-Term Agreements.
Transaction: Chicago Fire FC (MLS) signs midfielder Richard Fleming III to a Short-Term Agreement from Chicago Fire FC II (MLS NEXT Pro).
Name: Richard Fleming III
Position: Midfielder
Height: 5’8”
Weight: 154 lbs.
Date of Birth: July 7, 2004
Hometown: Libertyville, Illinois
Birthplace: Boston, Massachusetts
Citizenship: USA
Last Club: Chicago Fire FC II
