After graduating from Virginia in 2017, he joined the Brooks Beasts Track Club and has since set personal bests of 3:32.94 in the 1500 m and 3:51.26 in the mile. He is a two time US Indoor Championship runner-up and in April 2024, was part of a Brooks Beasts quartet that set the world record in the DMR.
In fall of 2013, Wynne enrolled at the University of Virginia, joining the Virginia Cavaliers cross country and track and field teams.[5] After redshirting his freshman cross country season, Wynne made his Virginia debut during the 2014 indoor season where he would run a personal best of 4:04.37 in the mile and go on to place eighth at the ACC Indoor Championships in the same event. Outdoors, he ran 3:46.48 over 1500 m and finishing his freshman season placing eighth at the USA Junior Championships in Eugene, Oregon.
In 2015, Wynne placed fifth at the ACC Indoor Championships in the mile and finished sixth as part of Virginia's DMR at the NCAA Indoor Championships.[6] In June, he qualified for the NCAA Outdoor Championships in the 1500 m, but failed to advance to the final.
During the 2016 indoor season, he broke four minutes in the mile for the first time, running 3:58.74 at the John Thomas Terrier Invitational in Boston.[7] In February, ACC titles in the mile and DMR, and on March 12, competing at the NCAA Indoor Championships in Birmingham, Alabama, he took first place in the mile in 4:06.63.[8]
After missing the 2016 fall cross country season due to a knee injury, Wynne placed second in mile at the 2017 ACC Indoor Championships in February and placed fifth at the ACC Outdoor Championships in the 1500 m. However, his high hopes of a strong showing at his final NCAA Outdoor Championships were squashed after a bout of pneumonia just before the East Regional Qualifier, causing him to place just eleventh in his heat, dashing his hopes of qualifying for a final NCAAs.[12]
Following his 2017 season and the conclusion of his collegiate career, Wynne signed professionally with Brooks, joining the Brooks Beasts Track Club under coach Danny Mackey. Just two days before he signed the contract, he underwent knee surgery, something him and Mackey had hidden from Brooks during contract negotiations, causing the Brooks sports marketing department to be "very unhappy" when they learned of it.[12][14]
Coming off his operation, he struggled through the 2018 season, but managed personal bests of 3:55.23 in the mile and 13:30.43 over 5000 m.
In early 2019, Wynne finished second at the USA Indoor Championships[15] and ran a mile personal best of 3:51.26, placing him sixth on the all-time US list at the time.[16] Later that year, he ran a 3:35.14 1500 m PB in Seattle and finished eighth in the at the USA Outdoor Championships.
In May 2021, he ran a 1500 m personal best of 3:34.08 to take fourth at the Portland Track Festival. The following month, at the 2020 US Olympic Trials (held in 2021), Wynne placed fifth in 3:37.70.[17][18]
At the Boston University Last Chance Indoor Qualifier in February 2023, Wynne ran his fasted mile since 2019, clocking a time of 3:52.51 to take the win.[20] At the 2023 USA Outdoor Championships in July, Wynne placed fifth in 3:35.99[21] and, in August, ran a 1500 seasons best of 3:34.67 to take the win at the Ed Murphy Classic in Memphis.[22]
On April 19, 2024, at the Oregon Relays, Wynne, alongside Brooks Beasts teammates Brandon Kidder, Brandon Miller, and Isaiah Harris, set a world record in the distance medley relay. After a 2:49.60 1200 m leg by Kidder, a 46.60 400 leg by Miller, and a 1:45.75 800 m split from Harris, Wynne anchoring the quartet running the 1600 m leg, needed a split in the low 3:50s to secure the record. Running completely solo, he ran a split of 3:52.63, breaking the previous record of 9:15:50 set by Kyle Merber, Brycen Spratling, Brandon Johnson, and Ben Blankenship at the 2015 IAAF World Relays, by 0.92 seconds with a time of 9:14.58.[23][24]