Jason Witten to Retire and Join 'Monday Night Football' as Analyst According to ESPN’s Todd Archer, Witten informed the Dallas Cowboys that he was going to retire. Witten reportedly told Cowboys owner and general manager Jerry Jones and head coach Jason Garrett that he will accept ESPN’s offer to be the analyst for Monday Night Football. It marks the end of the tight end’s 15-year career that was highlighted by 11 Pro Bowls and multiple NFL records. The 36-year-old Witten will return to AT&T Stadium on Nov. 5 when the Cowboys host the Tennessee Titans on Monday night.