The fit wasn’t there for the Leafs or Jimmy Vesey

Heading into the offseason, many in Toronto were all but certain that the team was walking out of a drawn-out free agency period with superstar centre Steven Stamkos and NCAA youngster Jimmy Vesey. Both felt like foregone conclusions, rather than fights they had to win.

Fast forward, and they’ve walked away with neither. Stamkos re-upped in Tampa Bay back in June, and today, the rich got richer as Vesey ended up with the New York Rangers. The Leafs did make a strong pitch for the 23-year-old, flying into Boston with Auston Matthews in tow and no doubt reminding him that his brother and father are part of the organization.

But it didn’t work. It’s a shame for a team looking to further bolster an overflowing prospect pool, but at the same time, it’s not the end of the world for either side, simply put, it wasn’t the right fit.

Above is a list of Toronto’s left wing forwards on entry-level contracts in the present, and also Jimmy Vesey, who will no doubt have received the maximum $925,000 per year with some gaudy bonus structure attached to it.

That expected contract, why teams were lining up for him. It’s not that they think that he’s the second coming of Alexander Ovechkin, so much as they recognize that they’re getting a low-risk, high reward addition if they secure his services. Succeed, and he’ll greatly outplay his salary. Fail, and he’ll be easily buryable in the AHL. Not to mention, thanks to his age, he’ll still be a restricted free agent at the end of his deal, meaning that you’ve in effect tied him into two deals, not one. 

Having players like that are particularly good if you’re a cap-ceiling team that needs to fill out your bottom six; that constant conveyor belt of B-level prospect talent running through depth roles has been key to the success of teams like Pittsburgh, Los Angeles, and Chicago. Toronto is going to have to do the same this year to alleviate the cap dumps and rookie bonuses of this year, and starting two years from now, they’ll have to do it to compete.

But as you can see, they also have an abundance of these types players on the left side. Many are within Vesey’s age group, not differing by more than a year or two. Some of the dual wingers might find themselves jumping over too, with Mitch Marner and William Nylander both being moved to from centre to that side to terrorize goalies for eternities to come. 

Jimmy Vesey would be another tool in the toolbox. In fact, he might just be the most potent one of the bunch, having put up very strong junior and senior years at Harvard. But I don’t think the margin is significant enough to lose sleep over; you have players like Leivo who are coming off monster AHL seasons and require waivers. You have players like Johnson, who crushed the SHL while two years younger, or Leipsic, who produced very well despite playing a more secondary role. Soshnikov looked very good in his NHL stint; Rychel could’ve been better with the Blue Jackets but many still believe the potential is there.

I doubt that any of these names are going to be superstars, but assuming that the Leafs, like everyone else, saw Vesey as a middle-six player, they still have a lot of options already in the system that can step in. Ultimately, his size and scoring prowess would’ve been nice, but it would’ve been a slightly brighter feather in an already filled cap.

As I said back in July, there are four factors that should matter to a player making a decision like this: opportunity, loyalty, familiarity, and money.

Toronto no doubt would have shown him the money; as we stated above, a maxed-out ELC still carries next to no risk to the team. But everybody else will be around to do the same, eliminating that advantage.

Loyalty is there, but that seems like it has a risk of being temporary. Yes, the Leafs employ Jim Sr, his father, and have his brother Nolan in their system. But scouts can and have been fired or not renewed at the drop of a hat, and Nolan is a far long shot from ever getting an NHL contract from the team. Does the family tie matter when it disappears in the second year of your tenure and you still have at least one more contract to go?

As for opportunity, what I mentioned for the Leafs goes the other way. I doubt Vesey is expecting to step on a competitor’s first line, but I think he wants a reason to believe that he’ll be on the NHL roster unless he proves to be a catastrophic failure (which is unlikely). It’s one thing to have a player breathing down your back as friendly competition; it’s another to have as many as ten of them. Not to mention, players like Colin Greening, Milan Michalek, Matt Martin, and Peter Holland might be standing in front of him in the present, which makes a tough situation even tougher.

That’s even more of a hurdle when you consider where the Leafs are in their rebuild. It’s a little easier to swallow a numbers game when you know you’ll be playing on a team chasing the cup, but as much as there’s a vocal minority that believe the Leafs are better than last year showed, making big climbs up the ladder from 30th still leaves you as a longshot for ring-chasing in the immediate. “Mediocre young team with a bunch of players who can knock you down a peg” is probably the least preferable situation when your other options are “big minutes on a roster shell” or “passenger on a winner”.

Toronto doesn’t exactly have much to offer him in terms of familiarity either. Again, he has the family, but neither are guarantees to stay around long-term. He doesn’t have former teammates here, and he’d be moving countries to take the chance here. Now, do the Rangers fit all of these parameters? It’s tough to say, but if he feels that way, it makes sense that he went through with it.

As much as one would like to believe that Toronto is destined to sign everybody, the Leafs were more likely a team that gave an effort in this race, but not one that seriously fought tooth and nail for the opportunity (though, if they did, losing their two biggest sweepstakes of the summer diminishes the whole ‘we get who we want’ narrative significantly). 

Teams aren’t doing their due diligence if they aren’t making every effort they can to become better in the short and long term, but barring a huge next step in his development, Vesey wasn’t going to change the world for the Leafs organization. He’d be another cog in the machine, and if he doesn’t feel that this is the place for him to immediately win, grow, feel at home, or gain a consistent income, what’s the point?

He’s waited this long for his right to choose, and we’ve waited this long to watch him make it. Some might be disappointed, but I can’t see either side having nightmares about it down the line.