Terms of the deal were not disclosed by the team, but TSN's Bob McKenzie reported earlier in the day that the two sides were closing in on a two-year contract that would be worth slightly less than $1 million per year.
The immediate question that follows all of that is simply ... why? What's the point of this move if you're the Maple Leafs?
Orr was eligible for unrestricted free agency this summer and was coming off a four-year deal with the team that paid him $1 million per year.
The issue for Toronto isn't that Orr is overpaid (though $1 million per year, or anything close to that, for a player that's strictly a fighter probably isn't the best use of a team's cap space), it's that he doesn't really do much to further Toronto's goal of becoming a Stanley Cup contender. Especially when they still control the rights of restricted free agent Frazer McLaren, who is not only the same type of player, but also probably wouldn't cost as much.
There's also the question of why a player whose role is strictly to fight not only needs a multiyear contract (like the four-year contract he originally signed), but then a multiyear contract extension after that one expires.
Toronto's fourth line was a constant weakness for much of the season because it put such an emphasis on dressing fighters and tough guys. It almost always ended up with the Leafs playing every game with a shortened bench because players like Mike Brown (before he was traded to Edmonton), Orr, and McLaren couldn't be counted on to play more than five or six minutes a game.
The Maple Leafs fought more than any other team in the NHL last season and that was often cited as a big reason for their turnaround. The popular storyline was that players like Nazem Kadri wouldn't be playing in fear with players like Orr around. The reality is that, like most fights in the NHL, Toronto's came at completely meaningless times in games and were either in the first three or four minutes, or late in the third period when the outcome was already well in hand.
(There was also the time Kadri had to fight Victor Hedman when Orr was on the ice with him.)
The other reality is that Toronto wasn't winning this season because of its "toughness," it was winning because of great goaltending and players like Kadri, Phil Kessel, and James van Riemsdyk scoring a lot of goals.
Still, Toronto seems to have embraced the mind-set that toughness leads to wins, and toughness means having a couple of guys like Orr around.
Even if that means giving them multiyear contracts.
We'll see if it works.