Grading the Toronto Maple Leafs Most Notorious Canada Day Moves

The Toronto Maple Leafs have historically made their mark on Canada Day.

The Toronto Maple Leafs have to be the most well-known sports franchise in Canada. No offense to the Toronto Raptors or Toronto Blue Jays, but the buds still run the city. That is despite a disappointment for the past 54 years.

Regardless, “Canada’s team” loves to make headlines on the country’s birthday.

That may be good or bad. Here are seven of the Toronto Maple Leafs’ recent headline transactions on Canada Day. (stats from hockey-reference.com and cap info from capfriendly.com).

2010: Brian Burke Adds a Pesky Former 1st Rounder

The Toronto Maple Leafs finished as the second-worst team in the NHL, behind only the laughable Edmonton Oilers. In response to that, general manager Brian Burke believed the team could use some size with a touch of offense.

To do that, he would sign a former first-round pick from the 2001 NHL Draft. That man was Colby Armstrong. His contract would pay him $3 million per year for three seasons.

What did the Lloyminister native do to earn that contract? For one, it was a weak free-agent class, which elevated his value. Another was the flashes of potential he showed in his rookie season and the ’08-’09 season.

He was more known for being a physical player, and that’s what he provided. The offensive production did not come along with it, though. He would put up 26 points in 79 regular-season games wearing the blue and white sweater.

Burke would go back on his decision to sign Armstrong two years into the three-year deal. The contract got bought out, and the forward would suit up for the rival Montreal Canadians the following season. It was a short stint that did not pan out for Colby or the team.

While it wasn’t the team’s worst move in the world, it did not work at all. Considering Burke was hoping to revitalize Colby Armstrong’s offense, the logic was there, but two very disappointing seasons was enough to cut ties. The $3 million cap hit remains a question, though.

Grade: C-

2014: NOT Re-signing this “Playoff Player”

The Toronto Maple Leafs were looking to return to the playoffs after a heart-breaking 2013 playoff run. To help the team on their run, general manager Dave Nonis traded for Dave Bolland. Heading to the Chicago Blackhawks was one second-round pick and two fourth-rounders.

Now, that wasn’t a TERRIBLE trade at first. The two-time Stanley Cup champion gave the Leafs a reliable defensive center with offensive upside (sounds familiar, doesn’t it?). He would become a number two or number three center (depending on if the team signed Tyler Bozak).

Gritty forward Zack Kassian cut Bolland’s season short by severing his Achillies tendon with his skate. He required season-ending surgery, and it would be the end of his short tenure with his hometown team.

In 23 games, the veteran only had 12 points and was a -1. I’m sure the then 27-year-old would have had a productive season, but maybe not as much as management thought. Regardless, his expiring contract and the horrifying injury cast doubt on his future with the team. While some believed Toronto shouldn’t re-sign the forward, it was the player that decided to play elsewhere.

He would sign a hefty five-year contract averaging $5.5 million per season with the Florida Panthers. Unfortunately, he would play 78 games for the Panthers over two years. Injuries crept up again and ended his career.

It’s unfortunate, considering Bolland had the intangibles and defensive qualities general managers love on their roster. That’s also why Nonis wanted to retain the forward. Luckily, Dave took his talent, and injury issues, elsewhere. His contract would take up $5.5 million despite not being on the ice.

It’s not known what the offer to Bolland was, but let’s say it was the same as Florida’s. The Maple Leafs thankfully did not have to deal with a large portion of $5.5 million in dead cap on their roster.

The only thing preventing the grade from being an A+ is the “what if” factor. Would he stay healthy if he had remained in Toronto? Was Nonis’ contract offer more reasonable? I doubt it, but I guess we’ll never know.

Grade: A

2015: The Penguins Get Some Thrill

After being a rocky team over the past couple of seasons, then Interim GM Kyle Dubas pulled the trigger on one of the biggest trades we have seen in a while.

To help the Toronto Maple Leafs head into a rebuild, they dealt star winger Phil Kessel, 2011 first-rounder Tyler Biggs, journeyman Tim Erixon, a 2016 second-round pick, and retained $1.2 million per year for the remaining seven years of Kessel’s contract. Whew.

Heading to Toronto was 2014 first-rounder Kasperi Kapanen, defensive prospect Scott Harrington, depth forward Nick Spaling, and a first and third-round pick in the 2016 NHL draft. If that’s hard for you to read, here you go.

Kessel would put up 303 points in 328 games and won back-to-back Stanley Cups in ’15-’16 and ’16-’17. That alone wins the trade for the Pens, but that’s not to say the Leafs lost.

Biggs and Erixon would not play one NHL game in Pittsburgh, and the second-rounder drafted forward Kasper Bjorkqvist. He has yet to solidify a roster spot in the AHL. Kapanen would become one of Toronto’s budding stars, putting up 80 points in his last 147 games with the team before being traded back to the Penguins. He along with Pontus Aberg and Jesper Lindgren gave the Leafs a 2020 first-rounder, Filip Hallander, David Warsofsky, and Evan Rodrigues.

Harrington split time between the Leafs and Marlies for one season before being traded to the Colombus Blue Jackets. Heading to Toronto was depth forward Kerby Rychel.

Spaling was a depth option in Toronto for the ’15-’16 season but got traded to the San Jose Sharks right after. That trade also included Roman Polak and gave Toronto two second-round picks and Raffi Torres.

The 2016 first-rounder got traded to acquire Frederik Andersen, and the third-rounder drafted James Greenway. At 23-years old, he still plays in the NCAA.

The $1.2 million retained on Kessel’s contract is still against Toronto’s cap, but it will expire after this season. With that, the Leafs will no longer have any direct ties to the blockbuster trade.

While the Pens benefitted by winning two cups, the Leafs benefitted by accelerating their rebuild. Kapanen and Andersen (from a trade using the 2016 1st rounder) were a part of four playoff runs with the Maple Leafs. The recouped assets from Kapanen’s return to the Pens were also handsome.  Not to mention that without making this trade, the Leafs probably are not bad enough to get the first overall pick and subsequently draft Auston Matthews.

Grade: B+

2016: Signing a “Big Man”

It seems as if the Toronto Maple Leafs are always in need of size. That’s because most of the team’s resources are toward high-end skilled players. Those don’t tend to be big or physical players.

Youngsters Auston Matthews, Mitch Marner, and William Nylander needed protection. To do that, general manager Lou Lamoriello signed hits leader Matt Martin to a four-year contract with a cap hit of $2.5 million.

I get it paying $2.5 million is a low cost when you’re trying to protect budding superstars. Martin’s presence had the opposition think twice before making a move on one of the rookies.

What made the bully more valuable, is his soft spot for his teammates off the ice. The locker room presence was visible, with Marner being the more obvious player to love Martin as a teammate.

While he wasn’t considered an offensive player by any means, the management wanted some offense from the guy. They weren’t expecting a 50-goal season, but 15 to 20 points in a season would be great. His six-foot four-inch frame could block off any goaltender’s eyesight.

Matt was expectedly underwhelming regarding putting up points, registering 21 points in 132 games. Ironically, his ’16-’17 season was the worst offensive season of his career. Eventually, the defensive play became an issue. Now, you’re paying someone $2.5 million per season only to hit and protect your young guns. That doesn’t fit when you need salary cap space.

After playing his entire career with the New York Islanders before signing in Toronto, Lou would put an Islanders jersey back on him. Ironically, Lou would do that as the new general manager in Long Island.

His young sidekick, Kyle Dubas, took it as an opportunity to do a favor and shed money at the same time. In return for the “goon,” the leafs acquired Eamon McAdam, which was Toronto dumping off Martin’s cap hit.

Going back to the signing, it didn’t provide that much to the team. The term and the money did not make sense initially and looked worse as the seasons went on. It couldn’t work, at least not in Toronto.

While the dollars were unfavorable, it wasn’t terrible. Thankfully, Dubas gave Lou the tough guy he loved. There wasn’t any return, but freeing up space was all that mattered.

Grade: C-

2018: Toronto Maple Leafs Bring in the Homegrown Star

The Greater Toronto Area is home to a large number of stars in the NHL. With the Toronto Maple Leafs having the passionate and loyal fanbase they have, you figured a big fish would sign with the team in free agency. Unfortunately, that hasn’t happened in years.

That was until the 2018 offseason. The first player to be granted exceptional status from the CHL to play in the league underage, a four-time 30+ goal-scorer, and a captain decided he wanted to go home. That was the 2009 1st overall selection, John Tavares.

Trying to convince someone as good a player as Tavares to sign with you is not an easy task. Kyle Dubas made sure he could put together the best pitch possible, and as it turns out, it worked. That included signing him to a seven-year deal worth $11 million per season.

He was the best player available in free agency in recent history. It makes up for the team missing out on players like Steven Stamkos and, though unrealistic, Connor McDavid.

The signing means the Leafs finally had something they lacked for a long time, multiple reliable centers. They now had Auston Matthews, Tavares, and Nazem Kadri. That’s three lines with centers that will torment opposing defenses.

I must say, Johnny T has been living up to the hype. If anything, he is playing better than expected. His first season with the Buds saw a career-high for points and goals scored. While not praised, he was winning faceoffs and controlling the puck at a higher rate.

His impact on and off the ice was clear to everyone. It was enough for the former Islanders captain to become the 25th captain of the Toronto Maple Leafs to start his second season in blue and white.

In all three seasons thus far, John has been more than stable defensively. That’s while averaging around one point per game. While it is not as flashy as playing offense, he averaged three hits, just over one and a half blocks, and just under two takeaways per 60 minutes played last season.

No, the Toronto Maple Leafs still haven’t had playoff success; however, this past season, Tavares couldn’t help the team due to a brutal concussion. That’s the only thing he has fallen short of thus far. For everything else, John Tavares was a fantastic signing for the Toronto Maple Leafs.

Grade: A+

2019: Offloading Lou’s Angels

People criticize or respect Lou Lamiorello’s willingness to stick to his instincts regardless of what others say. If he wants someone or wants to give someone money, he will do so with no questions asked.

While that way of thinking made his former teams successful, it did not work so well in Toronto. It resulted in a horrendous seven-year contract paying Nikita Zaitsev $4.5 million per season. Kyle Dubas desperately needed to get the contract off the books.

He looked to the Ottawa Senators and added in Connor Brown and the rights to Michael Carcone. Despite the offload, the Maple Leafs acquired a third-round pick, Ben Harpur, and the contract rights to Cody Ceci and Aaron Luchuk.

Zaitsev played well in his first season coming from Russia. While he was a -22, he managed to put up 36 points. That was enough convincing for Lamiorello to give him that huge contract.

Unfortunately for Lou, Zaitsev would pick up only 27 points in his next 141 games with the Leafs. While Lou has had his great moments, this wasn’t one of them. Connor Brown was a sixth-round pick from the 2012 NHL draft. He burst into the NHL, putting up six points in seven games as a rookie and 36 points in 82 games the following season. He would put up 28 and 29 points respectively the next two seasons.

Carcone was an undrafted free agent who has been a solid AHL player that has yet to play in the NHL. Overall the Leafs saved $5.875 million for the following season and $4.5 million for the next five seasons. Freeing up cap space was the priority of the trade for Kyle Dubas.

The 2020 third-rounder sent to Toronto was one of two draft picks traded away for Jake Muzzin. Harpur played one season with the Marlies before being traded to the Nashville Predators for Miikka Salomäki.

Ceci signed a one-year deal worth $4.5 million and left in free agency the following year. Luchuk failed to earn a spot on an AHL roster and played in the ECHL for the past three seasons.

The Sens got Brown, who has been a solid piece for them, but Zaitsev is still playing underwhelming for his contract. The Leafs traded for a top-notch second-pairing defenseman and freed up a lot of space, but the Ceci experiment did not work out.

Overall, Toronto surpassed their goal of the trade, and that was to free up cap space. For that, you need to give Dubas credit. While the Ceci experiment panning out would make this a perfect situation, not everything always works out. It was still worth a one-year trial.

Grade: A-