During the summer it was reported he asked for a trade out of Toronto due to him having a lack of opportunity to play productive minutes. His agent, Dan Milstein stated that it was more about his terrible play than anyone on the team. The Leafs refused his request and said they would find a spot for him to play more. Fast forward 80 games and almost a full season and Mikheyev has not only become arguably the Leafs best penalty killer, but he has also become a third of the leagues best third line. He and the Leafs outscore opponents when he is on the ice shorthanded and he leads the league in shorthanded goals. On top of that, he is scoring at a 31-goal pace playing third line minutes while making a small $1.65M.
With the season Mikheyev is having, the Leafs would've been smart to engage in contract talks earlier in the season, but until they knew where the cap would be it would've been difficult. In addition to other expiring contracts, Mikheyev is in line for a career payday, with Luke Fox claiming he is worth between 4 and 5 million should he hit free agency. Given the Leafs relations with his agent Dan Milstein, and that the Leafs found a spot to play, with the ability to slide up in the lineup, would lead to a more reasonable AAV.
If Mikheyev continues to play the way he is, including in the playoffs, I wouldn't be surprised if you see someone like Engvall, or Kerfoot go to make some money.