[2] His opinionated "tell it like it is" style made such an impression that he was hired as a color analyst for Cleveland Indians television broadcasts.

After being replaced on the Indians telecasts, Drennan was hired by WHK AM 1420 in Cleveland to host a sports talk show.

In the late 1980s, he took over WWWE's long running Sportsline evening sports talk show, replacing Pete Franklin.

Throughout the 1990s, Drennan worked on and off for WWWE (which in 1996 became WTAM) as a morning sports anchor, and towards the end of the decade returning to the evening slot to host Sportsline.

In September 2004, Drennan's home in Strongsville, Ohio was raided by FBI and IRS agents as part of a sports-gambling investigation.