Every single year there’s a free agent on the open market that signs a contract that everybody, even the team that signs it, is going to be an albatross sooner rather than later. Generally speaking, you’re signing a guy to push you over the top in the short-term and sweeping under the rug how that’ll hurt you long-term.

The Oilers made a signing like this with Milan Lucic in 2016, the Capitals did it last year with T.J. Oshie, and somebody this summer is going to do it with James van Riemsdyk. Coming off of a 36-goal season, JVR is going to get paid. He’s an effective player and he does the most important thing in hockey, which is scoring goals, but he won’t be worth the money he’s going to command.

He’s a guy with really good timing. Heading into his first unrestricted free agency of his career, van Riemsdyk scored 36 goals for a Maple Leafs team who enjoyed their best regular season in franchise history.

JVR took a few years to break into the league after bring drafted with the second overall pick in the 2007 by the Philadelphia Flyers. He spent two years at the University of New Hampshire before joining the Flyers in 2009-10, helping them on their surprising run to the Stanley Cup Final. After just three seasons in Philly, JVR was dealt in a hilariously lopsided one-for-one deal for Luke Schenn.

After joining the Leafs, he finally broke out as the elite goal scorer that made him the second overall pick. He reached the 20-goal plateau in four of six seasons in Toronto and the two seasons he didn’t were shortened due to the lockout and due to injury respectively. All told, JVR 0.37 goals-per-game and 0.71 points-per-game over 413 career games in Toronto.

I imagine the Leafs would love to keep him around, but it isn’t financially feasible for them unless he’s willing to take a big discount. Toronto has to pay RFA William Nylander this summer and then they’ll have to pay Mitch Marner and Auston Matthews the following summer. Despite what Leafs fans will tell you, those three will come in somewhere around $25 million annually, leaving the team little room to keep a guy like JVR who’s going to turn 30 years old next May.

Honestly, in theory, he’s a great fit with the Oilers. JVR is a big body with incredible hands and an uncanny ability to score goals. He’s a one-trick pony in the NHL, as he doesn’t hit, intimidate, play a two-way game, or anything like that, but the thing he does is really, really important. It’s also the thing that gets you paid in the NHL. He scores goals.

JVR has some of the best hands around the net in hockey. He’s a big body so he isn’t easy to push around in front of the net and when he gets the puck fed to him in the danger zone he has the skills and poise to pick corners from in tight. It’s fun to visualize JVR playing with Connor McDavid. I’m imagining JVR parked in front of the net, McDavid skating around, finding him, and JVR doing stuff like he did in the video I posted above.

He would be an excellent compliment to McDavid given the fact he’s one of the NHL’s best finishers, but, unfortunately, the Oilers can’t invest heavily in another winger at this point. They already made their big free agent splashes with Milan Lucic, Andrej Sekera, and Kris Russell, so it’s almost impossible to find the money to fit in the $6.5-7 million that JVR will command on the open market.

Beyond that, as good as I think JVR is at the thing he does, I’m skeptical of the long-term viability of him being a top scorer in the league. He’s going to be leaving a system in Toronto that’s very offensively oriented. Also, in that situation with the Maple Leafs, JVR was heavily sheltered on a line with Tyler Bozak and Mitch Marner who were fed heavy offensive zone starts against weaker competition.

There’s a risk that he might not thrive in a new system or in a role with more pressure. So given the fact he doesn’t have a skillset to fall back on, signing JVR to a star player contract would be a massive risk for the team dishing it out.