WWYDW: Deadline Day Strategy

The Toronto Maple Leafs are better than most people expected they would be. In fact, maybe they’re actually good. This was evident in last night’s gutsy win over the Winnipeg Jets. Emotions were high, the Jets are a fast, skilled, and physical team with the ability to get under your skin, and the atmosphere at the Air Canada Centre was rocking. But the young Leafs squad didn’t get rattled. came back from down multiple one-goal deficits, killed a last-minute penalty at the end of regulation, and took the game home in overtime. 

After games like this, it’s hard not to wonder what this team could do in the playoffs, especially with a weak Atlantic Division around them. The trade deadline is a week from today. If you were the Maple Leafs front office, what would you do heading into the deadline? Treat yourself as a contender and buy? Stay the course and worry about the long-term? Or find a way to get creative and do both? 

The Leafs have a ridiculous amount of draft picks hoarded in their cupboard. This year, they have their own first, second, fourth, fifth, sixth, and seventh round picks along with San Jose and Ottawa’s second round picks (the middle of those three picks will be sent to Anaheim for the Andersen trade). Next year, they have all of their own minus their third again, but have another San Jose second rounder. They’ve already stockpiled a ridiculous amount of talent in the past two drafts, as they drafted ten times in the top-90 in 2015 and 2016 combined. 

So with that in mind, should the Leafs use some of these assets to grab a player that can help them win now? They certainly have the draft pick and prospect capital to not only nab a decent depth player or two, but they could grab one of the better players on the market, like Martin Hanzal, Kevin Shattenkirk, or Patrick Sharp. 

I really don’t see this happening, but it’s still an option. Roman Polak, Matt Hunwick, Ben Smith, and Curtis McElhinney are the only impending unrestricted free agents on the Leafs roster that could be used as rental sales. Beyond that, though, James van Riemsdyk, Leo Komarov, and Tyler Bozak are all productive players who are on deals with one more year of control left. 

It’s no secret that this is a seller’s market. The false parity in the league has made it so that literally everybody other than the exceedingly bad Coyotes and Avalanche think they go on a playoff run. It’s ill-advised, of course, as the list of actual Cup contenders in the league right now is very small. But put yourself in the shoes of a small market, mediocre team, and what a playoff run can mean to your fanbase and profit for the season. 

If so few teams are selling, maybe the Leafs can capitalize and sell guys like Bozak or Komarov for more than they usually would be able to, especially considering the added value of that extra year of control. 

This is probably the most likely option. The Leafs are better than expected this season, and realistically could make the playoffs without making a single change to their roster. That would allow them to appease a fanbase hungry for playoff action, give their young core experience in games that matter, and not stray from the process that has ultimately landed them such a bright future. 

In a salary cap world, it’s incredibly difficult to pull off major moves during the season. This year that reality is even more prominent as the looming expansion draft has added another element getting in the way of blockbuster deals. 

But the Leafs are in an interesting position. They’re young and good, and also very, very cheap, as their combination of entry-level talent coupled with their savvy use of the long term injured reserve has left them with a ridiculous amount of cap room at the deadline. 

With that in mind, the Leafs can take on awful contracts in order to help teams free up room to make rental moves of their own. They did this last year with Brooks Laich, and it netted them Connor Carrick and draft picks, which was certainly worthwhile. 

Maybe taking on a few ugly contracts for the rest of the season in return for more draft pick capital would make the Leafs comfortable with paying a hefty price for, say, Kevin Shattenkirk? Maybe the Rangers would be interested in giving away Rick Nash so they can protect a younger player at the expansion draft, and then JVR could be used to acquire one of Anaheim’s soon-to-be-exposed good, young defencemen. 

The options!