Cherry should have been canned years ago. He is just a gimmick. If your main selling point is the suits you wear, you clearly don't have much to sell. I stopped watching Coaches Corner years ago because I knew exactly what he was going to say before the suit commercial had ended. He always appealed to the lowest common denominator, brought very little insight to the game and was like that drunk uncle at a wedding that wants everyone to know what a great success he could have been. Good riddance.
Now if Roger's Sportnet want a replacement there would be no one better than Mr Rick Bowness. Widely respected around the NHL by players, GMs and fans. Years of experience. When I've heard him speak on radio or TV he always comes across as a classy guy. He would be my vote. But of cause, Rogers has to decide whether they want pure entertainment or try a more cerebral option.