His first taste of radio experience occurred in 1994, when he guest-hosted a show on WFAN as a result of winning a contest held by the station. He then hosted a sports-talk show on a radio station in Elizabeth, New Jersey before returning to WFAN as their overnight host in 1995. He continued as overnight host until November 2004, when he was moved to middays to co-host with Sid Rosenberg after Rosenberg's previous co-host, Jody McDonald, did not have his contract renewed with the station. After Rosenberg resigned from the station on September 12, 2005, Benigno became the sole host of the midday show until January, 2007, when he was then paired with Evan Roberts.