It was June of 2017, and the Oilers were in conversations with the Leon Draisaitl camp about a long-term contract extension coming off his entry level deal. Conversations, might be a bit generous. Things were pretty much at a standstill.



Then-Edmonton general manager Peter Chiarelli ran into Draisaitl’s agent Mike Liut in Chicago at the draft and there wasn’t much to be said.



“I’m not avoiding you,” Chiarelli told Liut. “I just can’t think of anything else to say that bridges the gap.”



It’s just how it goes sometimes when there are no hard deadlines to get a deal done. In this case, they had months before training camp would open so there wasn’t a ton of motivation to move in talks. It wasn’t until Aug. 16, that same year, where common ground was met on a new contract.



That Draisaitl deal, eight years at $8.5 million per season, would end up being one that executives around the league...