As Christmas quickly approaches, so does the trade deadline. With some key UFAs on the Leafs roster, they need to decide sooner or later what’s going to happen to them. While this may not affect the Leafs at all this season, it’s a good idea to see who should stay, who should go, and who should come in their place, and know what to expect next season.

Last, but definitely not least, is James van Riemsdyk. Acquired for Luke Schenn (that’s 1-for-1) back in 2012, JVR is currently in his sixth season with the Leafs, and has been very good, to say the least. While you can say a lot about his defensive ability, there isn’t much to say about his offense, except for “Wow, he’s pretty good at putting the puck in the net”. Best known for his hands in front of the net, JVR has put up 265 points in 368 games with the Leafs, and is definitely their biggest free agent this season.

The Leafs are a contender, as suggested by most sportsbooks, and won’t be dealt at the trade deadline. A sportsbook like Pinnacle Sports will have favorable odds, so check them before placing some action. 

While the other four UFAs can be argued to be replaceable, the same argument cannot be made for JVR. Since joining the Leafs in 2012, his 265 are the most by any Leaf during that span, although playing in the third most games does help him. Regardless, he’s fourth in points per game, behind only Phil Kessel, Auston Matthews, and Mitch Marner. He’s also first in power play points with 80, and first in game winning goals. Likewise, he has the most points in the postseason during the two playoff appearances the Leafs have.

This one will be the toughest loss, if it happens, but that’s the business side of sports. If JVR’s asking for too much, the Leafs can’t really keep him. Luckily, the Leafs have some good depth on the wing, so if they do let JVR walk, they should have an NHL-ready player slip right in, even if they aren’t at JVR’s level.

While Josh Leivo may be the guy that’s been sitting in the press box more, Kapanen is probably the best option the Leafs have in the system to replace JVR. The main haul of the Phil Kessel trade (not including the pick that was then traded for Andersen), Kapanen has the most upside, and has the best chance of producing to the level that JVR did as a Leaf. Whether he will or not remains to be seen (he hasn’t really gotten much of a shot besides the fourth line), but Kapanen has the talent to produce a lot at the NHL level, we’ll just have to see how it translates.

The other guy suffering from the Leafs depth on the wing, Leivo has actually done a really good job producing in the limited time that he’s gotten this season. In the last two seasons, he has 12 points in 23 games, and ranks 7th on the team in points per game. Keeping in mind his limited ice time, he ranks 8th in the league in 5v5 P/60 with a minimum of 200 minutes, ahead of players like Patrick Kane, Johnny Gaudreau, Evgeny Kuznetsov, Leon Draisaitl, even Auston Matthews. I’m not saying he’s better than any of those players by any means, but the fact that his production rates are better them is something to consider. Maybe being put in a better and more consistent role will allow him to flourish. But, like Kapanen, it’s hard to tell at this point.

Like Leivo and Kapanen, Brown has gotten the short end of the stick when it comes to ice time. You could argue that maybe another winger that rhymes with Byman should be on the fourth line instead of him, Brown has only seemed to crack the top nine when injuries occur. Even more surprising, he hasn’t been on the power play, with Babcock instead opting to use Leo Komarov for unknown reasons. Despite this, Brown is on pace to score 20 goals again this year. While not as good as JVR, Brown plays a similar style, and is a bit better defensively as well, so whatever he doesn’t have in offense, he could probably make up for defensively. Only time will tell, but Brown could certainly be an option for them next season.

Kane would probably the best free agent option for the team if they felt like no one in the organization could replace JVR, and JVR is firm on not re-signing with the team. He’s a couple years younger, and is having a career year on an otherwise horrendous Buffalo team, and he isn’t even seeing a significantly larger shooting percentage than his career average. His off-ice issues are a concern, especially in an organization as tightly-run as the Leafs, so if that is something that draws them away, I’d probably lean towards James Neal. But, Kane is the better player, so that’s why I picked him, despite hating my morality with every letter I type.

Why not replace JVR with JVR? While the other four UFAs are replaceable, and probably aren’t worth the price they’d ask for (or are worth nothing regardless), JVR might be the only player where re-signing him won’t be a negative effect on the team. While there’s no truth to it, JVR has seemed to imply that he doesn’t just want money with his contract, but probably also wants to play for a contender. If he signs a deal with them that is relatively cheap and not overly long depending on the price, it probably wouldn’t hurt to keep him around. He’s also really into fitness, so he could be one of those athletes that age doesn’t take as much of a toll on. It’s hard to say, but more likely than not, JVR would be worth the price of re-signing, especially if he wants to sign a cheap deal to stick around on an elite team.