The Toronto Maple Leafs are going to have a hard time winning any trades at the NHL Trade Deadline this year because they're the Toronto Maple Leafs.
That may sound like a strange statement, but it's true. Not only are the Toronto Maple Leafs the biggest hockey market in the world, but for many other factors, it's quite possible that the team won't be able to conduct as much business as some other markets.
If you look at some of the biggest names available right now, there's a big correlation between former executives or current rivals. For example, the New York Islanders, Montreal Canadiens, Pittsburgh Penguins and Boston Bruins are a few teams that the Leafs would love to trade with, but because they're the Leafs, it's not going to be easy.
Let's start with the NY Islanders. The man running the Islanders is Leafs former GM Lou Lamoriello. As much as Brendan Shanahan stated the plan was always for Lamoriello to go into an advisory role after his 3-year term was done as Leafs GM, I don't know if that is fully true.
Toronto Maple Leafs Don't Benefit From Being Toronto Maple Leafs
This is all speculation, but Lamoirello was hired as President of Hockey Operations and GM of the NY Islanders, only 30 days after his contract ended with the Leafs, so it's quite possible that he's still bitter from that decision by Shanahan, as he was clearly still a formidable executive. Lamoirello may look at his former club and say that he'll need a much bigger return for Brock Nelson or Noah Dobson if he wants to do business with them, as that tenure ended potentially worse than it may appear.
This same logic can be applied to the Penguins, who have a few players the Leafs would love. They probably can't acquire Evgeni Malkin or Sidney Crosby, but I think the Leafs would love to acquire Richard Rakell, or even Erik Karlsson, if possible. However, do we really think that Kyle Dubas is going to gift the Leafs anything?
Dubas, by all accounts, wanted to remain with the Leafs, but the team didn't grant him that wish and fired him, despite being one of the youngest and smartest executives in hockey. As a result, it feels like the Leafs may have to gift Dubas multiple of his favourite former prospects, in order to do business.
Then there is Treliving and Calgary, his ex-team that pretty much refused to deal with him after he left. While the other teams listed here are merely speculative, there is actual bad-blood between Treliving and his former team and a trade between them seems unlikely at this time.
As for the Montreal Canadiens and/or Boston Bruins. The Bruins recently traded away Trent Frederic, who would have been a perfect Leaf, yet that never would have happened because they share the same division. Trades between Boston and Toronto have happened in the past, but it would have taken a way bigger return for the Bruins to ever think about doing business with the Leafs.
The same logic applies to the Canadiens, as it seems unlikely that these two things would make a big splash. Similar to Boston, there have been trades between these two franchises, but it's rare, and usually isn't a huge move. David Savard would be a great addition to Toronto's blue-line, but I can't really see that happening as Montreal would prefer to do business outside of the division.
I know that other franchises have issues with in-division trades, but it feels like the Leafs will have to go above and beyond to make a deal, because they're the Leafs. They pay the tax of being the most popular franchise in hockey and it's definitely a disadvantage that maybe we don't look at as closely.
We'll see what happens on Friday, but hopefully the Leafs can bypass that mantra and make a big splash.