Why are the Leafs scaring off free agents?

Over the past eighteen months the Leafs have had their share of headline-making moves, no doubt. The biggest was the addition of Babcock on a record-setting coach’s contract, then they followed that up with the lower-magnitude but perhaps more shocking hiring of Lamoriello. Let’s just get that housekeeping out of the way. 

From there, notable trades happened, they quietly trudged through the season, and then the Auston Matthews lottery was won. It almost started to feel like under this Shanahan-run show, even beyond the high-profile management changes, Toronto was starting to make its own luck. And they still had room to grow quickly, with two free agents out there – both big names in different ways – with major ties to the team.

It was easy to get wrapped up in that hype and picture both Steven Stamkos and Jimmy Vesey as part of the Leafs’ core going into this fall. You could just keep going back and saying things “I thought they wouldn’t get Babcock either, but they did…” or “Phaneuf seemed unmovable, but they traded him…”

A lot seemed to be breaking right, and considering how the situations were playing out with those mentioned free agents – a 26-year-old elite player from Toronto going all the way to open free agency, and half Vesey’s family working for the Leafs – it wasn’t unreasonable by any means to see things leaning in their favour again.

But for some reason, they didn’t. The rebuild that seemed to be accelerating ran over a board of nails, and we all got a bit of a reality check.

And don’t get me wrong, this isn’t a post about dark clouds settling in on this club again. You can be pleased with the overall direction of the organization and still ask questions when something unfortunate happens. Both are indeed within everyone’s abilities.

The Stamkos story is easily the strangest of the two. It seems simple: A player totally within his rights to explore the market wanted to see how playing for his hometown team might look, then decided they wouldn’t be good soon enough, and stayed put. But if you believe some of the reports out there, he left the biggest cap hit in the entire league on the table to do that. Toronto had the money, the family, and the god status to offer, and didn’t make Stamkos even think hard about it. Or put another way, made him very quickly think hard about how awful a decision it would be. There were even rumblings that the Leafs including the CEO of Canadian Tire in their pitch was key in driving him away. That seems unbelievable at first glance, but then almost too believable when you’ve lived in the world of MLSE like we have. Either way, something bizarre happened there, and the Leafs struck out. Actually they barely got to the plate.

While not as grabbing as Stammergeddon, the Vesey saga played out with some surprises as well. The teams with their names connected to the college free agent the most over the last year seemed to be Boston (where he’s from) and Toronto (where his father works, and brother plays). What was a two-team race grew as he actually hit free agency last week, with Chicago and others joining in. Then the Rangers seemed to pop in out of nowhere and scoop him up.

Yes, I know the Leafs weren’t the only team to miss out here. But I’m only focused on them, and I’d love to know how a pitch from the Rangers pushed Toronto out of the running. New York has been a fine team for a while, but anyone with a brain sees them on their way down, prospect pipeline empty, and juggling some cap hits that will keep hurting. There isn’t a ton to sell, but they sold it, somehow, and the Leafs couldn’t.

The argument could be made that Toronto couldn’t offer Vesey a guaranteed top six role, but that’s sort of a bullshit out. No team can fulfill a promise like that, they can just say they will, and then however things play out over the next three years is how they play out. Hockey isn’t baseball, few players nicely fit into set positions for any amount of time. The Rangers may have told Vesey he’s getting top six minutes, but they could toss him to the AHL by year two for all we know. I don’t buy that as an excuse for the Leafs, at all. Sign the guy, worry about your lines at game time. 

I realize bringing all this up doesn’t offer any answers to why the shine has seemed to wear off the Leafs a bit, but it’s a question I’m asking. Is their approach in these negotiations too much about playing selflessly, something we’re told Lamoriello swears by? That would be strange considering he landed Kovalchuk, the best free agent of the last decade. Is MLSE too involved here, making these meetings seem a little too corporate and bland? Could there be too many voices in the room, creating an overwhelming atmosphere?

It’s probably unfair to speculate too much, but it’s just truly surprising to see that the success the Leafs have had in securing the eye-popping names for management hasn’t really translated to doing the same for on-ice talent. Especially when it appeared the free agent targets they were after had Toronto written all over them.