Kyle Dubas has shown that he isn't afraid of making a big trade in an effort to improve the Leafs playoff chances and, as you may know, so far it hasn't worked out. Apparently there was an especially embarrassing playoff loss last year, but I've blocked out any memories from approximately May 20th at 7:10pm until May 31st at 10:30pm so I have no idea what you're talking about.
This season instead of focusing on a team need, perhaps the focus should be on the highest entertainment value trade. Can't be any worse, right? I talked to some league executives and here are their picks for the most entertaining Leaf trade targets.
1) Phil Kessel
There's no question that the Arizona Coyotes are sellers at the deadline, like literally selling everything. Does your arena need a popcorn machine? make an offer! Adding Kessel to the Leafs offence probably doesn't move the needle much, if at all, but it sure would be nice to wear that jersey you've got in your closet again. Also something, something hot dog joke.
Entertainment value: 2 out of 5. It's too obvious a choice and that hurts it's score. So, how about a different former Leaf..
2) Luke Schenn
The one time future captain of the Toronto Maple Leafs. He never lived up to his draft hype, but almost 10 years since he last played a game for the Leafs he's still kicking around in the NHL. This season with the Canucks he has 2 goals, which exactly matches the number of Stanley Cup rings he has! Clearly he "knows how to win"(TM) making him a no brainer of a trade target. And just look at this hit!
Entertainment value: 5 out of 5. Nostalgia is all the rage so why not reboot a former 1st overall pick, and if the Leafs miraculously win the cup in 2022 nothing would make it more surreal then seeing Luke Schenn do a lap with it.
3) Patrik Laine
Crosby vs Ovechkin, McDavid vs. Eichel, Matthews vs. Laine. The media was ready for a new rivalry, two incredible goal scorers drafted back to back, both to Canadian teams. There were awkward radio exchanges where it was declared by some that Laine would be the superior player, it was going to be a career long rivalry! Unfortunately, Laine didn't live up to his end of the deal and has struggled the last couple of seasons. However, he's a 3-time 30 goal scorer and goals are fun, defence is boring, so lets add him to the Leafs powerplay and just see what happens.
Entertainment value: 4 out of 5. I took one point off because I didn't like the optics of two 5 out of 5's in a row, after all this is a professional list that needs to be taken seriously. Bonus point would be added if confused Winnipeg fans still chant "Laine's Better" when playing the leafs.
4) Zdeno Chara
He's been the mortal enemy of the Leafs in the playoffs for too long. In a weird way this trade seems like it could make sense. The islanders look like they could be sellers this season, Chara is on a one year deal and would probably like to be traded to a playoff team, and the ask probably wouldn't be too high. Add to those reasons that absolutely no NHL referee would give the 45-year old Chara more than one interference/cross-checking penalty per playoff game, so after he gets it out of the way he could basically do whatever he wants the rest of the game. Yayy playoff hockey!
Entertainment value: 2 out of 5. Points were removed because he's a veteran NHL player (not named Jason Spezza) so the Leafs would end up putting him on their 1st pairing and top powerplay unit.
5) Brett Ritchie
Admittedly this one is more of a masochist pick, but adding B. Ritchie would definitely get people talking, or tweeting, or whatever. We have one Ritchie who's underperforming, well why not double down and get a second. Perhaps putting them together would unlock some sort of brother connection and get them both going. Also, who cares about the Rocket Richard race when we could have front row seats to the Rocket Ritchie race. Currently Nick is winning with 2 goals to 0, but still plenty of time left!
Entertainment value: 3 out 5. The thought of a completely out of nowhere Leafs PR tweet that we've acquired Brett Ritchie from the Calgary Flames makes me laugh. Do it.
So there you have it, the consensus picks from my very real league executive connections.