He founded and hosted ESPN Radio's AllNight with Todd Wright, and was a part of ESPN Radio from 1996 to 2005. Wright then took his popular national show to Sporting News Radio (later Yahoo! Sports Radio) in 2006 where it continued airing until 2012.
In addition, Wright served as host or analyst for multiple college football studio shows, general sports talk programming and Tampa Bay Rays World Series coverage on Sun Sports, a Fox Sports regional cable network in Florida, while also anchoring live tournament coverage for the PGA Tour Network and PGA Tour Entertainment.
Since his retirement from national radio, Wright often guest hosts the Steve Duemig show or other programming on 620 WDAE in Tampa. Wright and Duemig, as well as anchor/producer Darek Sharp, all worked together at WFNS, Tampa Bay's first ever sports talk radio station in the early 1990s.
During Wright's tenure ESPN Radio and later Sporting News/Yahoo! Sports Radio, his style often went against the conventional sports talk stereotype. Segments such as the "Lavish SportsCenter" co-hosted nightly with now current AllNight host Jay Reynolds, Freedom of Choice, Suicide Hotline and weekly Fantasy Drafts (Bobs & Roberts, sandwiches, SNL characters, etc.) were some examples of original programming. While he did make some early appearances on ESPN2 as a guest host, Wright's image never appeared on ESPN websites as Wright maintained to listeners that radio was meant to be a theater of the mind and it didn't matter what he looked like.
Wright is credited as one of the first national hosts to heavily incorporate pop culture into sports talk programming, famously traveled to all major sporting events, and was first to refer to the NBA as simply "The Association", among other sports' catchphrases.