Middleton was born on July 17, 1965 in Atmore, Alabama[1] to teenage parents. He and his sister were raised by their great-grandmother.[5] Middleton attended Escambia County High School.[6] In 9th grade, he attempted to quit football to play trumpet in band, dreaming of becoming a rock star, but his coach convinced him to focus on football.[7][8] He graduated in 1982 at age 16[7] and attended Auburn University, where he played tight end under Pat Dye and Wayne Bolt.[9][8] The Auburn Tigers had three bowl game wins while he was part of the team.[3] He graduated with a degree in pre-law and history.[10][11][8]
After retiring from playing in 1995, Middleton enrolled in a course to prep for the LSAT but quickly decided he was more interested in being involved in football. His friends convinced him to try coaching.[8] He joined Troy University in Mississippi as the tight ends coach in 1997 and expanded his focus to include offensive tackles. He was also assistant special teams coach.[14][9][2] After two seasons, he joined Ole Miss as tight ends coach. By the end of his five season run, he was also running backs coach and special teams coordinator and had coached players including Jonathan Nichols.[3][9][2] He was added to the Tampa Bay Buccaneers coaching staff in 2003 as part of the Bill Walsh Diversity Coaching Fellowship Program, then joined the team full-time in 2004 under Coach Jon Gruden.[2][13][9] Gruden chose him to attend the NFL's Coaches Career Development Symposium in 2006.[3]
Middleton was the head coach at the 2022 Senior Bowl for the National Team, which included players such as Jesse Luketa, Boye Mafe, Perrion Winfrey, J. T. Woods, Rachaad White, and Abram Smith, when the Jets were chosen to be one of the coaching staffs for the game. They beat opposing coach Duce Staley's team 20–10.[15] In May 2014, Middleton and Shawn Jefferson were invited to attend the NFL's coaching accelerator program at the league's spring meetings, which allowed them to meet with team owners.[16][17]
Personal life
Middleton is married to Kalita and has four children, Desmon, Ron, Zaria, and Mariah.[10][11] In 1998, he earned a Master's degree in sports and fitness management from Troy University.[9][10][11] He was inducted into the Atmore Area Hall of Fame in 2013.[18]