That is until CBC's Hockey Night in Canada came calling, and made the 40-year-old take a hard look at where his career was going. He opted to leave the bench and move back to the broadcast booth.
"Growing up, I remember sitting and watching one game a week, and it was Hockey Night in Canada, and feeling how much impact it had on hockey, and how much impact it had on people in Canada," Simpson told a news conference Thursday.
"The opportunity to move into that was a decision that didn't come easily . . . but also one that I realized may not come up again."
The offer prompted him to take a look at what he wanted out of coaching, he said. A head coaching position was the end goal, but he realized that would mean leaving the Oilers anyway, to take a position in the minors or with another NHL team.
Simpson, who has prior TV experience, said his 11-year-old son helped seal the decision with the comment "if we don't move, I don't care."
"I think the notion of maybe even going to Springfield, Mass., (the Oilers' American Hockey League affiliate) and taking that team, I felt from my family's standpoint and where I was, I didn't want to do that."
Simpson originally broke into the NHL in 1985 with the Pittsburgh Penguins before being traded to Edmonton where he won two Stanley Cups in six seasons. He retired in 1995 after playing two seasons with Buffalo.
He then worked for TSN, Fox Sportsnet and Rogers Sportsnet. Most recently he worked with Hockey Night in Canada after the Oilers failed to make the playoffs.
Simpson will be reunited with play-by-play partner Jim Hughson at CBC in a broadcast team expected to eventually take over the mantle from Bob Cole and Harry Neale.
He said he's looking forward to working with someone he respects and cares for deeply, and that it will make leaving another longtime friend - Oilers head coach Craig MacTavish - easier.
"You spend more time together than you do with your wife," MacTavish joked about his coaching relationship with Simpson. "It's been a special relationship, from my perspective."
Simpson said his time as a coach has made him a completely different broadcaster, and that he hopes he can keep those lessons fresh as he watches the game from a new perspective.
"The people broadcasting a game are up in that place where the game looks easy," he said.
"And if anything I hope to continually remind myself of just the intensity and the physicalness of the game that goes in, that you don't see up there."
It will be a challenge keeping his strong feelings about the team in check, Simpson acknowledged, but added he's assured his new bosses he's willing to cover the Oilers nationally.
"I'm certainly always going to be guarded on the negative, but I think your role has to be to deal with the situation that presents itself."
The search for Simpson's replacement will begin immediately, said MacTavish, adding it won't be easy.
"As a head coach, when you sit down and you get over the disappointment of losing one of your trusted allies, and you sit down and you say - 'OK, what do we have to replace?'
"It's a big task."
Meanwhile, CBC also announced that Hockey Night in Canada executive producer Joel Darling has been promoted to director of production for CBC Sports. Hockey Night senior producer Sherali Najak will succeed Darling.