Leafs looking to make difficult trades ahead of deadline

It seems like we’ve been counting down to the Leafs’ purge of cheap veteran players since the days they were signed last summer. In a little over a month, we’ll finally see what they get to show for them.

The most obvious names we’ve looked at all season are the pending free agents, and as the team currently sits, there’s seven guys on the roster fitting that bill – Polak, Reimer, Boyes, Parenteau, Spaling, Matthias, and Grabner. Eight if you include Rich Clune.

But we can’t forget about players who still have a year or five left on their contracts either. Lamoriello and his front office are still somewhat in scorched earth mode, and they might have a chance at moving out a name or two that saves the team some more coin down the road.

As James Mirtle noted in his column this morning, Lamoriello is becoming more heavily involved in trade talks these days. And while the pure rentals are the most likely targets, he’s also begun gauging interest in Jonathan Bernier and Daniel Winnik, two underperforming players with contracts through next season. 

But dealing players like this won’t be easy, even with their short term.

Out of the two, Winnik would presumably be the most sought-after, since he carries a more cap-friendly tag of $2.25-million. But his scoring is down and he’s also been a drag on possession, at least compared to last season. For $2.25-million, you could probably get three Daniel Winniks this summer, so I’m not sure why many teams would be interested. If the Leafs make a move here it’s likely going to involve some money coming back – whether that’s to give a contender more cap relief immediately, or it stretches beyond that, is obviously the big question.

It’s also somewhat of a surprise to hear Winnik’s name get dropped because he’s been unofficially carrying the title of “veteran guy who plays the right way”, tasked with helping the team and its prospects through the early stages of the rebuild. Remember, Winnik was dealt at last year’s deadline and then returned again to Toronto. That doesn’t happen often. He’s had as good a relationship with this team as anyone in recent years.

For Bernier, whose stock could not be lower, things are even more difficult. The goalie market is all over the place and the idea of investing a good chunk of cap dollars between the pipes is likely a frightening risk for a lot of teams. This might be the type of deal where bringing in an expiring big contract to help out a cap-strapped playoff team makes sense, but that team would still be on the hook for Bernier’s $4.15-million next season, so don’t expect much else. It would essentially be dumping him for nothing to free up Stamkos money.

These are some of the first real rumblings we’ve heard of players besides the pure rentals being shopped ahead of February 29th, and with Lamoriello you never know how things might shake out. The names mentioned here probably make for some difficult negotiations, but that’s precisely why he was hired.