Toronto Maple Leafs Roundtable: Best Trades of the Decade

Mike Stephens

The easy answer here would be the Dion Phaneuf trade to Ottawa. While riding the Leafs of one of the leagues most onerous and handcuffing contracts it also financially positioned them for a rebuild.

Although, that dead horse has been beaten enough. Instead, I’m going a little under the radar.

The best Leafs trade of the last 5-10 years occurred on February 28th, 2016, when Toronto sent Daniel Winnik and a 2016 fifth-round pick to the Washington Capitals in exchange for Brooks Laich, Connor Carrick and a 2016 second round pick.

Allow me to explain.

How Did it Shake Out?

In Winnik, the Leafs sold high on an asset that would actually be detrimental to their rebuild. In 2016, Winnik was still an effective defensive forward, something a team trying to lose games had little use for. Teams building towards a deep playoff run salivate over later in the year salivated over someone like Winnik, and Toronto was smart enough to utilize that advantage.

The Leafs then took Laich, or more specifically Laich’s contract, off Washington’s hands, albeit at a price. With a cap hit of $4.5 million and another year left on his deal, Laich was legitimately holding the Capitals back from true contention.

So, like they did for Ottawa, the Leafs agreed to alleviate this financial constriction for a price, which ended up in the form of a promising defence prospect in Carrick and the 2016 second-round pick.

The second round pick was used to select Swedish forward Carl Grundstrom, who seems poised to assume Leo Komarov‘s role once the latter departs in free agency. To date, Grundstrom has impressed mightily in his brief glimpses on North American ice and is garnering rave reviews from Toronto’s scouting and development staff.

In fact, were the trade simply Winnik for Grundstrom, it would be a win on its own. Say what you will about Carrick’s usage this year, but mustering a return consisting of a young RHD, and a projected top-six prospect in exchange for a third line winger is masterful.

Way to go, Lou.