After playing with the FC Dallas academy,[2] Reynolds became the club's youngest ever Homegrown Player on November 23, 2016, when he signed a contract with the first-team.[3] Although he played with the Dallas academy as a forward, Reynolds was used as a fullback with the Dallas first team.[4][5]
Reynolds was on loan to North Texas SC in March 2019.[6] Reynolds made his FC Dallas debut on May 19, 2019, against Los Angeles FC.[7] He recorded his first career assist on May 25 against Vancouver Whitecaps FC.[8] On August 27, 2019, Reynolds scored his first professional goal for North Texas SC in a match against Tormenta FC.[9]
On September 23, 2020, Reynolds signed a four-year contract with FC Dallas.[10] In October 2020, he was ranked in Major League Soccer's "22 Under 22" rankings.[11]
On February 1, 2021, Reynolds joined Serie A club Roma on an initial 6-month loan with an obligation to buy.[12][13]
Having seen limited minutes, Reynolds was loaned to Kortrijk in Belgium for five months in January 2022.[14]
On June 21, 2022, Reynolds moved on a season-long loan to another Belgian club, Westerlo.[15]
On 30 July 2023, Westerlo announced the permanent signing of Reynolds on a four-year deal,[16] for a reported fee of €3.5 million.[17]
He received his first call up to the senior United States squad in March 2021.[19] On March 28, 2021, Reynolds made his debut for the senior national team in a friendly against Northern Ireland.[20]
Reynolds was called up to the 2023 CONCACAF Gold Cup roster for the United States.[21] Reynolds started and scored his first senior international goal with a long-range effort against St. Kitts and Nevis.[22] Reynolds also started the final group stage match against Trinidad and Tobago.[23] He made his knockout stage debut versus Canada, starting in the quarter-finals and being subbed out in extra time as the United States advanced on penalties.[24]
