I'm going to preface this entry by saying there's no smoking gun here. Everything you read is pure speculation on my part, based solely on observations I've made as a fan of sports and sports radio.
In 2002, Rogers Media, a division of Rogers Communications, purchased CJCL, better known as The Fan 590. In 2011, Bell Canada's TSN Radio 1050 debuted. In response to that, "The Fan 590" was re-branded "Sportsnet 590 The Fan."
Since 2011, Bell and Rogers have been going head-to-head in sports media, both on television and on the radio. Bell has their stable of TSN analysts and personalities, and Rogers has their stable of Sportsnet analysts and personalities.