Chicago City Wire

Chicago Fire FC II has signed midfielder Richard "Trip" Fleming III to an MLS NEXT Pro contract through 2026, with a club option for 2027. The financial terms of the agreement 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," stated Alex Boler, General Manager of Chicago Fire II. "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."

Fleming, originally from Boston, Massachusetts, joined the Chicago Fire Academy during the 2017-18 season. He was part of the Fire U-19 team that won the U-19 MLS NEXT Cup in 2021. He made his debut with Chicago Fire II on June 26, 2022, playing all 90 minutes in a victory against New England Revolution II. In the same year, he appeared in 21 matches, starting 19 times and contributing two goals and four assists over 1,746 minutes.

"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 Gregg Broughton, Sporting Director of Chicago Fire FC. "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."

In 2023, Fleming played in 18 matches for Chicago Fire II, scoring two goals and assisting twice while playing various positions. His performance helped the team reach the MLS NEXT Pro Playoffs for the first time.

During his time at the University of Wisconsin-Madison in fall 2023, Fleming started all 17 matches he participated in during his sophomore year. He played over 1,000 minutes and recorded five goals along with three assists.

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.