Trey Wingo was born on September 19, 1963, in Greenwich, Connecticut, to Hal Wingo II, one of the founding editors of People magazine. He grew up in Greenwich, where he attended high school alongside future NFL Hall of Famer Steve Young. He later attended Baylor University, where he was a member of the Phi Delta Theta fraternity.

Wingo launched his broadcasting career in 1987 at NBC’s News at Sunrise in New York City. He later worked as a sports anchor in various local networks before joining ESPN in November 1997. During his 23 years at ESPN, he became the primary host of NFL Live and anchored multiple editions of SportsCenter. He also covered the NFL Draft extensively and hosted the Women’s NCAA Basketball Tournament. 

Trey Wingo left ESPN in 2020 after the network failed to renew his contract. He subsequently joined Pro Football Network as an equity partner in 2021 and shortly after became Chief Trends Officer and Brand Ambassador for Caesars Sportsbook. In  2024, he joined DraftKings Network to host Pregame PowerUp, an NFL Monday and Thursday night pregame show, though he parted ways with the network in 2025.