Toronto Maple Leafs Roundtable: Best Trades of the Decade

The trade deadline is three measly days away, and the Toronto Maple Leafs find themselves right in the thick of the rumour mill.

Although, while the focus is placed primarily on what the future may hold for the Toronto Maple leafs, allow me to suggest a different option:

In order to cleanse our collective pallets from the daily grind of “sources say” tweets, I think taking a trip down memory lane would be a fulfilling exercise.

This week’s roundtable question was:

What is the Toronto Maple Leafs best trade from the last 5-10 years? 

Boy, did the EIL staff come through on this one.

The Leafs are not exactly known for their great transactions.  From Robert Luongo, to Scott Niedermeyer, to Tyler Seguin, Dougie Hamilton and Richard Rekell, the Leafs are known for the exact opposite.  But there has been some good with the bad.

Mostly bad, we’ll admit it.   Burke had at least two good trades though, and Lou and the group working before Lou was hired have been, overall, very good.

Let’s check it out.

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.

Lauren Kelly

There have been some pretty great trades made by the Leafs to get the team to where it currently is now. The best one, in my opinion, is the trade that essentially flipped Jonathan Bernier and Frederik Andersen between Anaheim and Toronto.

Although they were technically two trades, the Leafs essentially acquired Andersen and a 2017 conditional draft pick (the conditions weren’t met) for Bernier, a 2016 first, and 2017 second rounder.

That was definitely a hefty price to pay for Andersen, who was a relatively steady but unproven goalie for the Ducks, because he hadn’t played much at a consistent level in Anaheim. He had been a part of that weird goalie carousel with John Gibson and Anton Khudobin, and Andersen’s final season in Anaheim was plagued with injuries.

Leafs fans weren’t really sure what they were getting in Andersen, but I remember them being relieved to see Bernier gone a few days later.

It’s as simple as this: a team’s goaltending is often the deciding factor in its success.

How Did it Shake Out?

Remember how terrible Montreal was when Carey Price was injured a few seasons back? The Leafs constantly rely on Andersen to bail them out, every single night he plays. And that goes for Curtis McElhinney too.

The Leafs would not nearly be as far up on the next Atlantic team if not for Freddy’s heroics on multiple nights this season. The Leafs paid a hefty price to get Freddy, but I think every Leafs fan can agree that it was well worth it.

If you’re still on the fence about it, just ask yourself where the Leafs would be if they didn’t have Andersen?

They have made excellent depth trades to try and elevate their team to perennial contender status. But this is the one trade I think they really knocked out of the park, and the trade that is the most important to where the team is now.

Because if you really think about it, the Leafs wouldn’t be anywhere without Andersen today. They might not have made the playoffs last season. And they definitely wouldn’t be where they are today.

Kyle Cushman

The date is January 22, 2014, when the Toronto Maple Leafs complete one of the biggest steals in NHL history. To Los Angeles, they send Andrew Crescenzi, a big, tough centre who had just two points until that point with the Toronto Marlies. In exchange, Dave Nonis and co. received Brandon Kozun.

How often do you see a team acquire a Canadian Olympian in exchange for a bottom six AHL centre? To me, this is a no contest, the Crescenzi-Kozun swap is by far the best trade for the Leafs in the last five years.

Now, the Leafs actual best trade of the last five years, in my opinion, occurred on the eve of the 2016 trade deadline. In a late night deal, the Leafs sent Daniel Winnik and a 2016 fifth-round pick to the Washington Capitals.

In exchange, Toronto took back Brooks Laich and his albatross contract, as well as defensive prospect Connor Carrick and a 2016 second round draft pick. This trade was pretty good at the time and is only getting better as we see how the prospects pan out.

Taking on Laich’s deal for two years wasn’t of much concern for Toronto. Receiving a quality right-handed defensive prospect to go with a relatively high pick made it a worthwhile deal for the Leafs to make, and boy is it starting to look good.

How Did it Shake Out?

Toronto didn’t lose much in the deal, with Winnik ageing and the pick only becoming Beck Malenstyn, who has become a decent prospect for the Capitals. The return is looking very interesting.

Laich is now gone, with his insane cap hit off the books. Carrick is a young, NHL quality, right-handed defenceman, and those players are hard to come by.

The most intriguing aspect of this deal, however, was the 2016 second round pick, which Mark Hunter and the Leafs scouting staff turned into Carl Grundstrom. Grundstrom has emerged as a quality prospect that could make the jump to the NHL sooner rather than later.

Already signed to his entry-level contract, Grundstrom has an impressive 25 goals over the past two years in the SHL with Frolunda. He got a taste of the North American game in the Calder Cup Playoffs last season and was dominant, recording four points in six games.

The fact the Leafs got two prospects of this nature for Winnik and a meaningless cap hit is a huge success, and one of Toronto’s best trades of the last five years.

Eduardo Razo

Goaltending tends to mask or solve a teams problems, and over the past ten years, the Toronto Maple Leafs have looked for a star netminder. They’ve made trades to fix this issue, whether it’s Vesa Toskala or Jonathan Bernier, but neither was a fit.

Finally, on their third attempt, the new Toronto brass made a trade for Frederik Andersen. Thus, ushering in the best deal, the organization has made in the last decade.

Over the last two seasons, Andersen has stabilized the position for Toronto.

Using Goals Saved Above Average (GSAA), Andersen has prevented 16.96 goals this season which doubles his total from last season (8.58). Furthermore, five of his 51 starts would file under Really Bad Start (RBS), and his Quality Start Percentage (QS%) is at .588 which is above-league-average.

How Did it Shake Out?

Andersen gives Toronto a chance to win night in and night out, and it’s no shocker that they are one of the top teams in the league.

Now, some will argue that this is recency bias but look at the previous two trades they made to sure up their woes in net. Toskala had an okay first season in Toronto with a QS% of .563; however, his GSAA was a -9.30 which is his best number during his tenure.

The following season his GSAA went from bad to worse with -27.09, so he was hurting Toronto at this point.

Bernier was a bit better, in his first season he averaged a GSAA of 15.07 in ’13-’14. There was a reason why Toronto collapsed that year and missed the playoffs after he went down with an injury.

Then it went downhill after that as he averaged -3.91 and -8.15 respectively in his last two seasons in Toronto.

With average QS% and unable to prevent a significant about of goals to bail out his team, Bernier became the latest goaltender who failed to cut it in Toronto.

Ask teams like the Philadelphia Flyers what it would mean to have a goaltender who performs at an elite level. For the first time in a long time, Toronto has an undisputed number one center and an undisputed number one goaltender.

That makes the Andersen trade the best of the decade.

Wilbert Timmermans

Easy, the Phil Kessel deal. That’s a no-brainer, for sure!

There are two big trades that gave the Toronto Maple Leafs a chance to properly re-build the team, the Dion Phaneuf deal, and the Kessel deal. While both deals were beautifully orchestrated by Lou Lamoriello, the Kessel deal still yields a tangible return in Kasperi Kapanen, reminding us how good the deal has been for Toronto.

If that wasn’t enough, that deal got rid of one of the worst trades Brian Burke ever made, landing Tyler Biggs in the 2011 NHL draft.

Kapanen, who was drafted 22nd overall by the Pittsburgh Penguins in 2014, has been a big part of the rebuild. He is finally, and I mean seriously, what took Babcock so long, playing for the Leafs regularly.

How Did it Shake Out?

In potential, he could become a top 6 forward while already being a top 9 forward, despite being played as a fourth-line winger. Bizare enough, Babcock stated that Kapanen is still auditioning for his pot, I mean come on, get your act together, Babs.

There’s a second reason why the Kessel deal is the best, and it might be an unpopular opinion, but hey, I can’t help it.

Kessel deserved to play for a team who appreciated him and actually provided him with a chance to play for the Stanley Cup. Kessel did an amazing job on a broken Toronto Maple Leafs team, created by the state of the art garbage management, the Leafs had back then.

I think it is safe to say Lamoriello has been great for Toronto on the trade market.

And if the Kessel deal didn’t impress you. Then look into the Frederik Andersen, Brian Boyle, Calvin Pickard, and Dion Phaneuf trades. Just to name a few.

John Krpan

Undoubtedly, the best trade for the Toronto Maple Leafs in the past five years was made in their division with the Ottawa ‘Can’t sell out a playoff game’ Senators.

The Trade

Ottawa receives: Dion Phaneuf, Matt Frattin, Casey Bailey, Ryan Rupert, Cody Donaghey.

Toronto receives: Jared Cowen, Colin Greening, Milan Michalek, Tobias Lindberg, 2017 second round pick.

Ottawa Break-Down

Donaghey and Rupert are currently playing in the ECHL and do not have an NHL future. Frattin is currently playing in the KHL.

Bailey is surprisingly holding his own in the AHL, and Phaneuf was the only positive for the Senators in this deal and they just traded him away to the Kings for a salary dump (and STILL had to retain salary).

Toronto Break-Down

Cowen was a nightmare administratively and cost the Maple Leafs a few bags full of cash. Greening and Michalek were good vets for their stint in the AHL. And both guys helped the Leafs suck to the bottom, so they could draft Auston Matthews.

Lindberg was traded for Calvin Pickard, probably the second best AHL goalie in the league at this time.

This guy could really get us something of value at the trade deadline or at the draft. The second round pick was used to select Eemeli Rasanen. A six-foot-seven, right-handed defenseman that will either be a bust or the next Zdeno Chara.

What Ottawa really got was screwed, and what Toronto really got was Matthews and a behemoth RHD that may or may not do anything for the team in the long haul.

Final Verdict: Leafs win.

James Tanner

The best trade the Leafs have made in the last ten years is trading Francouis Beauchemin to the Ducks for Jake Gardiner and Joffrey Lupul.

Lupul gave the Leafs a few good years, but what makes this one of the best moves in franchise history is the acquisition of Jake Gardiner. Gardiner, despite being unfairly made into a whipping boy by certain segments of the fanbase, has been an excellent, consistent player for the Leafs and has become a legitimate top-pairing defenseman.

In 469 games as a Leafs, Gardiner has, despite playing on some truly awful teams, made it so that the Leafs have gotten over 50% of the total shot attempts he’s been in the ice for. Not to mention 51.5% of the total goals!

That’s right, despite all his supposed errors (in reality they’re no more frequent than anyone else’s, you’re just watching him closely) Gardiner has, for almost 500 games, be a net positive.  That is  a fact, and it’s especially gratifying because it’s a sample size big enough to use goals only, and you don’t have to get anyone to buy into anything as “crazy” as shot-attempts.

Gardiner ranks 68th in all-time Leafs scoring, 12th among defenseman. He has at least 30 pts in 5 of 6 full seasons with the Leafs, and despite what people might think, the evidence says that he is an excellent shot-suppressing defenseman who impacts his team defensively in a positive manner.

Next: Stop Trading Liljegren

Like it or not, Gardiner is one of the best Leafs defenseman of all-time, and ,if not for the existence of Michael Grabner, would be the most underrated player in the NHL. The trade to acquire him is easily the best Leafs trade of the last decade

Thanks for reading!

stats from Naturalstattrick.com