The Toronto Maple Leafs are clearly in the midst of a transition. Over half the publicly-known staff has been fired, many players have been traded, and many will be walked away from. But it seems like there’s still a lot left to come in terms of roster shuffling; the group from Game 82 will almost assuredly not be the one that skates on the ice for Game 1 in October. 

It takes two to tango, though, and in the New Jersey Devils, the Leafs may find a dance partner.

It doesn’t take a genius to recognize that a rebuilding team like the Leafs are going to get rid of some of their veteran assets, particularly when talking about players that were available at the deadline but held on to in hopes of higher eventual return. 

With that said, the big boss called out the roster in his exit chat this week, removing all doubt of a shift.

“This isn’t to single anyone out; it’s not good enough, and [the players] understand that,” Shanahan said. “I haven’t been satisfied with it. They would all have to look in a mirror and agree that, as a group, it didn’t get done. I think when you look at championship teams, it’s really about a group effort when it comes to leadership.”

Nobody expects twenty men to all have the wished for “come to Jesus” moment over the course of the season, let alone bets on it happening, so a shakeup is the logical route.

Well respected New Jersey beat reporter Rich Chere spoke to Lou Lamoriello on Sunday regarding the Devils’ stance on their first round draft pick. Lamoriello stated that if the Devils didn’t win the lottery on Saturday, that he would consider trading his first round draft pick (currently ranked 6th, could fall to 7th), admitting that “you have to be open to anything.”

Furthermore, Lamoriello hinted at Ryane Clowe’s concussion possibly being career ending. This would clear 4.875 million per season off of the books for the Devils. This is on top of the money cleared in trading Jaromir Jagr (3.5 million) and Marek Zidlicky (3). Michael Ryder is likely due for a paycut (3.5) if he stays, and both Patrick Elias and Tuomo Ruutu will potential be in the same boat next offseason. In the grand scheme of things, the Devils could have close to $18 million to work with next year, with raises only really expected for Adam Larsson and Eric Gelinas.

Lamoriello pointed at a specific need for scoring help this offseason.

Depending on what the Devils are looking for, the Leafs have a bunch of options. Along the wing, they’re expected to be taking offers on Phil Kessel, Joffrey Lupul, and possibly James van Riemsdyk as well.

Of these, you have to imagine that Van Riemsdyk makes the most sense for the Devils. He has the most cap-friendly contract of the three, is a much better version of what they were hoping for Clowe to be, is the youngest of the group and, as icing on the cake, is from Middletown, New Jersey. 

If the Devils are looking to replace the star power they lost when Ilya Kovalchuk left for the KHL, however, Kessel could be a good fit. The added benefit to that thought too, is that if Kovalchuk does indeed to decide to come back in a year or two as rumours have hinted at, they could instantly have one of the best top lines in the league. 

Lupul would be the risk-reward option out of the three. His cost will undoubtedly be less, and he could theoretically bring lots of upside, but his extremely cold end of the season and scary injury history could lead to cautious thoughts.

In an ideal world, the Leafs will aggressively push for that pick in a move involving any of the players in question. Obviously, none would be a one for one swap; van Riemsdyk’s beneficial contract would likely lead to the Leafs asking for a prospect in return, Kessel’s sheer abilty would likely require a higher end prospect and another roster player to be involved, and the Leafs would be the team adding in the event of a Lupul trade.

I’m not too hot on the idea of trading Kessel right now (more on that later this week), but if I’m the Leafs, I’d seriously look at trading Lupul and the Nashville 1st rounder to get New Jersey’s pick. Maybe it doesn’t require the first; maybe you can convince the Devils that Roman Polak is the perfect replacement for Zidlicky and throw in a lower pick or prospect to seal the deal. If you go the van Riemsdyk route, the pick and somebody like (2012 second round pick) Damon Severson could be palatable.

If you can pull a move like this off, the Leafs have every opportunity in the world to make this the defining draft in the rebuild and really hit the gas pedal on the turnaround. Acquiring New Jersey’s pick leaves them with the two picks in the top ten, in a draft loaded with talent. Depending on how the lottery balls fall, they could pick up an impact forward with their own draft pick (Connor McDavid, Ryan Strome, or Mitch Marner), and then proceed to shore up their defence by picking up Ivan Provorov afterwards. If they stay in 4th/5th and somehow end up with Noah Hanafin, there’s a good chance they could end up with Mikko Rantanen as their forward.

Either way, if Toronto is able to pry this pick from Lamoriello’s hands, it leaves them in a good position to radically improve up front and at the blueline in a single day. As for the vacant left wing position, this gives them room to slot in William Nylander or Connor Brown next year, or a Winnik/Santorelli-esque free agent pickup.

Or, you know, nothing could happen. This is all speculation, after all.