Why the Leafs are the right fit for Jimmy Vesey

Last night, news broke that Nashville Predators prospect Jimmy Vesey was going to run out the clock on his contract rights and refrain from signing with the team, opting to become an unrestricted free agent as soon as he’s eligible to on August 15th. We talked about the possibility of Toronto being involved, but we never quite brought it into the “why” component of the equation. Let’s talk about that for a bit, shall we?

Obviously, there’s a lot of why on the Leafs’ side of things. The team has a clear intent to become the mecca of sustainable long-term success, and there’s no easier way to do that in the salary cap-driven era than to find cheap, young assets and develop them.

Vesey, in theory, looks like he’s he’s a low-risk prospect, in the sense that he’s already developed physically and has proven himself to be an effective, skilled, and imposing forward in back-to-back Hobey Baker finalist calibre seasons with Harvard University. NHL scouts have considered him “ready to contribute” for at least a year now; there’s a good chance that he could help the Leafs in the present just as much as he can in the future. But what’s in it for him? Well…

Family Matters

Vesey’s family is the frequently mentioned elephant in the room, in the sense that the Toronto Maple Leafs are about thirty steps ahead of everybody else in this regard. While you’d think the Boston Bruins would make the most sense for a native of North Reading, Massachusetts to have an association to, it’s been continuously noted that his brother Nolan was drafted by the Leafs in the sixth round of the 2014 entry draft and that his father Jim Sr. works in a scouting role with the blue and white. 

Obviously, the idea that the Leafs planned for this is a little suspect. Nolan will have been Leafs property for over two years when Jimmy hits the market, and his father had ties with Brendan Shanahan and even threw his hat into the ring for a job before the team had ever approached him. But nobody is going to sit here and pretend that having either direct relative doesn’t play into Toronto’s favour either; it’s definitely a boost.

Positional Depth

While the Leafs have loaded up on prospects across the board, it’s not like there’s a ton of competition on Vesey’s left wing. Brandon Leipsic, Andreas Johnson, and Dmytro Timashov likely lead the way on left wing, but Leipsic’s game leans more towards the bottom six, Johnson has yet to play in North America, and Timashov is a few years younger and yet to have played professional hockey. Players like Nikita Soshnikov, Connor Brown, and Zach Hyman can play on the left side if needed but prefer the right. 

Even when you look at the veterans in his position, you get James van Riemsdyk and a bunch of players who probably aren’t in Toronto’s plans. Joffrey Lupul is on the IR more often than he isn’t. Milan Michalek and Colin Greening are playing well enough that they could be moved out by draft day, let alone the end of next season. Brad Boyes is unlikely to be renewed. Needless to say, if Vesey is capable of playing with the big boys, he’ll have every opportunity in the world to do so here.

A Backup Plan

But what if, after heading into training camp, Leafs management’s expectations are a little more conservative and they decide that he just isn’t ready? First off, if that’s the case, he wouldn’t have had much of a chance elsewhere; as we alluded to up in the previous point, there isn’t really much to compete against here, and pretty much every other situation in the league is going to be more difficult to break into.

Basically, if he’s going to fail to break through immediately in Toronto, he’ll fail to do so anywhere else. But as the historically good Toronto Marlies have shown this year, the Leafs appear to have a strong professional development plan in progress; a lot of money has been invested in ensuring the Marlies have NHL-quality support in everything from coaching to individual tutoring, to analytics, and even biometrics. Not just that, but they’re being used to shape a team that very obviously prioritizes young talent. Vesey’s goal is obviously to play in the NHL next year. But having the league’s most invested into farm system to fall back on is a great option if he isn’t as ready as everyone believes.

Degree of Understanding

The Leafs aren’t strangers to the idea of integrating college developed players into their organization; the signing of goaltender Kasmir Kaskisuo yesterday was a good example of that, but there are many others currently plying their trade at the college ranks under Toronto control, and more of playing on the big club right now. 

Look at this year’s roster and you’ll find Zach Hyman, Jake Gardiner, James van Riemsdyk, Mark Arcobello, Ben Smith, Tyler Bozak, Colin Greening, Matt Hunwick, and Daniel Winnik who all honed their craft in the NCAA. Greening (Cornell) and Arcobello (Yale) even came from the ECAC like Vesey will be. Gardiner and Hyman’s rights were acquired while still in college, which shows the organization’s willingness to take a chance, and Bozak was also a UFA when the Leafs signed him though he was undrafted.

In effect, this gives Vesey a few mentors to learn about the transition from, and a few examples of how the Leafs will not try any less to make him into a legitimate player solely because of where he started. 

Fits The Window

Vesey is a little bit old as far as “shiny new prospects” go, but that fits him pretty much in the middle of the secondary core of talent, at least from an age perspective. The Leafs have had 13 players (Hyman, Soshnikov, Brown, Leipsic, Connor Carrick, Morgan Rielly, Garret Sparks, Josh Leivo, Stuart Percy, Frank Corrado, Scott Harington, Viktor Loov, and Martin Marincin) with birth years between 1992 and 1994 play for them this year alone; a large chunk of that group is expected to be of NHL regular quality next year if they aren’t already there. 

Toronto will supplement this group with top end talent that’s both a little older and, as a result of recent top picks, a little younger, but the first core to go for a run will be littered with players that are directly in Vesey’s age class. Few other teams are wrapped around that age pocket; wouldn’t Vesey want to run with that opportunity?


Obviously, Toronto isn’t the only place that will be able to offer him an enticing reason to head their way. they’re not the only team that could use another left winger, they’re not the only team that can offer him access to his relatives, and they’re not the only team that can offer him a shot at competitive hockey in the next few years.

But certainly, the list that can offer him the complete package is extremely, extremely short. Will Toronto take advantage of that in a little under five months? That remains to be seen, and perhaps the moves they make along the way will give a better idea of whether it’s the right fit. But for now, it doesn’t seem like there’s much of a better one.

  • Benjamin

    You make great points! But all of the hockey reasons you quoted are equally true of Nashville as they are pretty weak at forward. Plus with Nashville he could have started now, earned extra cash and burned off a
    year of his ELC. So what gives?

    My guess (and its purely speculation) is that scouts (like Jimmy’s dad) get bonuses for finding/landing top players. I wouldn’t be surprised if Jimmy’s dad got a 6 figure bonus for helping the leafs land him. And it wouldn’t be tampering either, that is a Scouts job after all. In fact it would be crazy not to reward a scout who handed you a player like that on a silver platter.

    As for Boston, I don’t think Vesey gets the same opportunity as he would in Toronto or Nashville. And Jimmy’s dad ain’t getting a bonus if Jimmy signs in Boston.

  • Benjamin

    Boston is the competition here. Vesey and his entourage will look carefully of course. If they do, they’ll find the skeletons of Hamilton, Seguin and Kessel. Will they want to go to the Bruins, an organization that eats its young?

  • Benjamin

    Wouldn’t it be funny if the leafs signed Vesey and then traded him for Drouin? The leafs would be getting Drouin literally for free!

    And as good as Vesey is I doubt he has the talent or ceiling that Drouin has. And how much more is Tampa really going to get for Drouin now?

    • Benjamin

      What would be even funnier would be if the Leafs signed Vesey and then traded him to Nashville in a package for Ryan Ellis.

      Probably not sit too well with Vesey though! Unless the leafs gave his dad a million dollar bonus to ease the pain!

      • Benjamin

        From a hockey perspective Yzerman looses the trade no question. But that’s a foregone conclusion at this point. If reports are to be believed Yzerman was willing to trade Druoin for Robby Fabbri but St. Louis said no. How much better is Fabbri than Vesey? They seem to be pretty much equal to me.

        I don’t see how much more Yzerman can get for Drouin. What do you think his value is?

        In any event it was just a musing, I don’t actually think it will happen.

          • CMpuck

            Yes Fabbri is better than Vesey. But Vesey is a better than Hyman. Moreover Have you seen Druoin’s ahl numbers so far, his lost year of development, his poor ahl numbers, his attitude and the fact that it’s all a public embarrassment for Yzerman? He’s not fetching much more than Vesey at this point.

  • CMpuck

    I would hope the Leafs offer Milan Michalek as a personal assistant/understudy to amuse and assist Vesey. He could be his driver, caddie, fetch him coffee, Milan could excel in that role for the organization, even play in Vesey’s spot when injured.