Chicago City Wire

Chicago Fire FC has signed midfielder Richard “Trip” Fleming III to a short-term agreement, the club announced Saturday. Fleming will be available for the team’s home match against Los Angeles Football Club at SeatGeek Stadium in Bridgeview, Illinois.

Kickoff for the match is set for 7:30 p.m. CT. The game will be broadcast globally on MLS Season Pass on Apple TV, and locally on WLS 890 AM via wlsam.com (English), as well as Que Buena 105.1 through the Uforia app (Spanish).

Fleming, age 21, joined Chicago Fire II in February after two seasons playing college soccer at the University of Wisconsin-Madison. Before his college career, he was part of the Chicago Fire Academy from 2017 until fall 2023. He played with the Chicago Fire Academy U-19 team that won the U-19 MLS NEXT Cup in 2021 and made his debut for Chicago Fire II on March 26, 2022, against Orlando City B.

Most recently, Fleming scored two goals on August 4 to help secure a 6-1 win over Columbus Crew 2 at SeatGeek Stadium. He has been an important player for Chicago Fire II, which was named MLS NEXT Pro Team of the Month for July following back-to-back Team of the Matchweek performances by Fleming in Matchweeks 20 and 21.

So far this season, Fleming has appeared in 17 matches (16 starts) during the 2025 MLS NEXT Pro campaign, scoring a career-high seven goals and recording two assists with a pass completion rate of 90 percent. Over three seasons, he has played in a total of 55 matches and logged 4,651 minutes.

This marks Fleming’s first short-term agreement with Chicago Fire FC. According to Major League Soccer rules, clubs may sign players from their affiliates (MLS NEXT Pro or USL) to up to four short-term agreements—each lasting up to four days—per season (a maximum of sixteen days). A player can appear on up to four regular season match rosters each year but may play in no more than two regular season matches; there is no limit on non-league appearances under these agreements.

“Transaction: Chicago Fire FC (MLS) signs midfielder Richard Fleming III to a Short-Term Agreement from Chicago Fire FC II (MLS NEXT Pro).”

Fleming is listed as a midfielder standing at five feet eight inches tall and weighing 154 pounds. He was born July 7, 2004, in Boston and grew up in Libertyville, Illinois.