Sitting inside Harbour Sixty Steakhouse, the white tablecloth restaurant just across the street from the Air Canada Centre, Jeff O’Neill considered a difficult question about life after hockey. It can be a hard transition, he said: “I’d probably be in fucking trouble myself if I didn’t have a job at TSN.”



The 40-year-old is a co-host on OverDrive, the afternoon drive show on TSN 1050, and he is a regular on the network’s television hockey coverage. For a decade before that, though, he was a National Hockey League forward, a first-round draft pick who made stops in Hartford, Carolina and Toronto.



He ended his career in Toronto, and he would often eat lunch with Mats Sundin at the steakhouse where he was now sitting with a reporter. O’Neill had 237 regular season goals, but had no post-career plans.



“I got lucky,” he said. “But for other guys? I don’t know. You get an ego, right? It’s...