Being from Boston he has a rather interesting history here.
Howie Carr is a local radio guy who is syndicated around New England. About 20 years ago (before the Rutgers thing), Imus and Carr had some sort of beef. Imus, on air, made a direct comment that Carr's wife had slept with Riddick Bowe (a famous heavyweight boxer for the uninitiated). It clearly was false, and Carr's wife started suffering harassment from Bowe's camp because they thought she had made up the rumor.
She hired Alan Dershowitz to sue for slander. They settled out-of-court, with an undetermined sum that was confirmed to be at least seven figures. Made the slightly-rich Carr family a bit richer.
Never really pushed me to ever be interested in listening to his show.