[6] He began wrestling for Liberty High School, where he became a three-time MSHSAA state champion and compiled a record of 163–6.

[14] After failing to make it to the 2016 Summer Olympics wrestling team, Winn relocated to California in 2016 to continue training mixed martial arts.

[17] Winn was scheduled to make his promotional debut against Markus Perez on June 22, 2019, at UFC Fight Night 154.

[19] On June 16, it was reported that Silva was forced to pull out of the contest due to a potential anti-doping violation by USADA and was replaced by returning veteran Eric Spicely.

[26] Winn was suspended for nine months and fined $1,800 of his purse by the Nevada State Athletic Commission on September 3, 2020, after testing positive for amphetamines.

[31] However, Winn was forced to pull out from the event, citing separated rib and torn cartilage,[32] and the bout was rescheduled at UFC Fight Night 194 on October 9, 2021.

[38] However, just two days before the event, Winn was forced to withdraw after fainting and falling down a set of stairs, at the UFC Performance Institute, sustaining a minor concussion.

[citation needed] He has openly talked about his late father's homelessness and alcoholism, and his older brother's drug addiction.