I used to listen to him on my three hour commute from Western MA to Portland Maine. He was a fun listen. He had great guests and he knew what was what in politics.
He never offended ME. And if he had, I would have stopped listening.
After conservative Howie Carr pointed out how old Imus was--he'd be dead by the time his new son got to college--Imus made a crack about Howie's wife, on air. She's not a public person and threatened to sue. Alan Dershowitz helped the Carrs get a financial out-of-court settlement. Howie has said that paid for his Florida condo. At one point Carr tried to jump to WTKK-FM Boston, which got rid of the Imus show after the Rutgers comment, and Howie was in line to get that morning time slot. A court ruling kept Howie on WRKO AM until 2014...by which time WTKK had changed format anyway.