The History of Trades Between the Toronto Maple Leafs and Boston Bruins

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We reach our first heavy hitter in the Toronto Maple Leafs trade history with our first Original Six team.

With a mutual history spanning the course of 96 years, the Toronto Maple Leafs and Boston Bruins have had ample opportunity to make some notable trades.

Quite a bit of action was done prior to 1967 expansion with 25 transactions made between the clubs from 1924 to 1967, most of which the swapping of minor league players.

Post expansion is a much different story. In the 53 years since, Toronto and Boston have completed 13 deals, including just one in the past 10 years.

This, of course, is no surprise due to the ever-growing rivalry between the two clubs. In the original six era of the NHL, you were forced to make trades with your rivals. If you didn’t, you were limiting yourself to two or three trading partners. In modern NHL history, that isn’t an issue for teams. Most teams avoid trading in division outright, with the exception of some trade deadline rentals as we’ll see later in this article.

Still, despite the relative lack of activity over the history of these two rivals, it’s fascinating to see just how many trades made between the Leafs and the Bruins have turned out to be significant ones in the history of the franchises.

From pillars in net to great goal scorers and future Hall of Famers, this Toronto Maple Leafs trade history has it all.

The Most Recent Trade

Leafs Acquire: Joe Colborne, 2011 1st (Rickard Rakell), 2012 2nd (Mike Winther)

Bruins Acquire: Tomas Kaberle

At the 2011 trade deadline, the Toronto Maple Leafs finally pulled the trigger on the Tomas Kaberle trade. After much speculation, the pending unrestricted free agent waived his no-trade clause to be moved to the Bruins to help with their Cup run.

Kaberle was in the midst of another very solid season with Toronto, leading the defence in scoring with 38 points in 58 games at the time of his departure. As a pending UFA on a weak Leafs team, it made no sense to hold on to him and let him go in free agency.

Instead, Toronto was able to get one of Boston’s top prospects in Joe Colborne, a 2011 first, and a conditional 2012 second if Kaberle re-signed with the Bruins or if Boston made the Cup final.

The trade worked out wonderfully on the Boston side of things. After 24 games in the regular season with the Bruins in the top four, Kaberle dropped down to a bottom pairing role in the Stanley Cup playoffs and flourished. 11 points in 25 games tied him with Dennis Seidenberg for the team lead in playoff scoring on defence, despite playing nearly 12 minutes less a night.

The depth Kaberle gave the Bruins was significant in Boston’s run all the way to the Stanley Cup finals, where they upset the favoured Vancouver Canucks to win their first Stanley Cup since 1972.

Although Kaberle did not re-sign with Boston, signing with Carolina instead, just making the Stanley Cup meant the Leafs also received Boston’s 2012 second-round pick.

In terms of pure value coming out of a rental move at the deadline, Brian Burke and the Leafs were superb. They got the Bruins consensus top prospect, their upcoming first-round pick, AND a second-round pick for a player on an expiring deal. Now, what did the Leafs do with the assets they acquired? Not much at all.

We’ll begin with Colborne. Coming off of a strong two-season career at the University of Denver, the former 16th overall pick had struggled in his first pro season at the time of the trade. He saw his production go from under a half point-per-game with Providence to 0.8 PPG in his 20 game stint with the Marlies.

In the next two seasons, Colborne would remain with the Marlies for the most part, seeing his scoring slowly increase. In spot duty with the Leafs, he was hit or miss. In 2011-12, his five points in 10 games gave a positive indication of what could be to come. In the lockout-shortened 2012-13 season, he got just five NHL games where he went pointless.

That brings us up to the pivotal 2013-14 season, where needing waivers for the first time Colborne would have to remain on the Leafs roster. The Nonis run Maple Leafs decided he hadn’t done enough to earn the roster spot in the preseason, and not wanting to risk him being claimed via waivers, traded him to the Calgary Flames for a conditional fourth-round pick.

Colborne would enjoy three solid seasons in Calgary, peaking with 19 goals and 44 points in 2015-16 (which would’ve been second on the Leafs in the same season) before flopping in Colorado and finding himself out of hockey by 2018.

Though Colborne didn’t pan out, something that is bound to happen with some prospects, the Leafs simply wasted the picks they got in the trade.

For starters, Burke used the 30th overall pick to move up in the 2011 draft to select Tyler Biggs, a trade I already discussed in the Anaheim Ducks trade history.

As for the 2012 second, Toronto used that pick to acquire John-Michael Liles.

At the time of the trade, it looked like the Leafs clearly came out on top of the Kaberle deal. As the years have ticked away, it’s clear that Toronto didn’t capitalize on the assets they acquired. Even something as simple as holding on to the 30th overall pick and getting Rickard Rakell for themselves makes the trade a win for Toronto. Instead, the Bruins have the 2011 ring and the Toronto Maple Leafs have next to nothing to show from it.

TORONTO, ONTARIO – NOVEMBER 15: A closeup of the Toronto Maple Leafs . (Photo by Bruce Bennett/Getty Images) /

The First Trade

Date: December 21, 1927

Leafs Acquire: Jimmy Herbert

Bruins Acquire: Eric Pettinger, $15k

Technically the first trade completed between the Toronto Maple Leafs and Boston Bruins was on December 8, 1924, but that trade was just a minor league player for cash.

The first trade where a player was sent either way came early in the 1927-28 season.

Both the Bruins (6-4-4) and Leafs (5-6-3) were off to mediocre starts to the season. Looking to make a change, the Bruins sent one of their top scorers in Jimmy Herbert to the Leafs, receiving prospect Eric Pettinger and more importantly $15,000 in return.

Herbert was coming off of a down season in 1927, failing to reach the heights of his 26 goal, 35 points 1925-26 campaign. With eight points in his first 12 games to start the new season, Toronto took a swing on adding the 30-year-old in the hopes it would spark their offence.

And that it did. The Leafs jumped from the seventh-best offence in the NHL in 1926-27 to the fourth-best in 1927-28. Despite the boost to the offence, Toronto failed to make the playoffs. The Bruins went from a high scoring team to a defensive unit, making the playoffs despite scoring the seventh-most goals in the NHL.

The 1927-28 season would be Herbert’s lone with the Leafs, as he would be flipped to Detroit at the end of the season for depth defenceman Jack Arbour and $12,500.

As for the Bruins, Pettinger would make his debut the following year to disappointing results. After going pointless in his first 18 games with Boston, he would be traded back to the Toronto Maple Leafs, essentially making the trade the sale of the Bruins’ top scorer.

BOSTON, MA – APRIL 04: Phil Kessel #81 of the Toronto Maple Leafs skates . (Photo by Maddie Meyer/Getty Images) /

The Biggest Trade

Date: September 18, 2009

Leafs Acquire: Phil Kessel

Bruins Acquire: 2010 1st (Tyler Seguin), 2010 2nd (Jared Knight), 2011 1st (Dougie Hamilton)

It’s rare that you see a trade of this magnitude between in division rivals in the NHL, but just before the start of the 2009-10 season, Brian Burke pulled off a blockbuster.

Everyone here knows how this trade panned out, so let’s give more context as to what it was like when the deal first went down.

Phil Kessel was a restricted free agent and the Bruins were struggling to put a contract together. A deal in the range of a four year, $16-million contract was rejected by Kessel early on in the offseason. Whether Kessel requested a trade is debated, but it was clear Kessel and the team did not see eye to eye.

Even at the time, Burke recognized the extremely high price being paid. But given where the Toronto Maple Leafs expected to be with Kessel in the lineup, it was a price that made sense on the surface.

Kessel was coming off of a massive third year in the NHL. Playing 16:34 a night, his 36 goals were most on the Bruins and would have led Toronto by 11. Just four years removed from being selected fifth overall, the Leafs were banking on Kessel coming in and being the star player that takes them over the edge to becoming a playoff contender.

It was quite the gamble, to say the least. Toronto had just finished last in the Northeast Division with 81 points, 12 out of a playoff spot. Despite the significant ground to make up, Burke believed that the addition of Kessel would make them competitive right away. In fact, he said so almost verbatim the day of the trade.

That’s exactly where the Kessel trade fell flat on its face. The 2009-10 Toronto Maple Leafs were abysmal. Injuries, lacklustre play, and brutal goaltending all combined to make Toronto the second-worst team in the NHL.

If the Leafs were even moderately competitive the first two seasons with Phil Kessel, the trade is likely one of the best made in recent Leafs history. Kessel led the team in scoring every year he was in Toronto, but he rarely had any help. That was especially true in his first two years with the Leafs, the two most important ones as it would decide what value the Bruins would get out of the trade.

And that’s exactly why things just never worked in Toronto. Kessel not only had to carry the team on his back, but he also had to live up to the expectations of a player acquired for a second overall pick, a ninth overall pick, and a high second-round pick. It was too much to overcome and hurt his stance within the fanbase essentially from Day One.

Boston receiving Tyler Seguin and Dougie Hamilton out of the Kessel trade made this the worst-case scenario for Toronto. Not only did they lose the second overall pick and a future first-line centre in Seguin, but Boston also hit a home run on the ninth overall pick a year later and snagged one of the premier defencemen in the NHL today.

The only silver lining that Leafs fans can find in the price paid to get Kessel is that the Bruins failed to get much value for either Seguin or Hamilton. Boston got three high-end seasons from the pair before shipping them out for mediocre returns, a vast contrast to the return they got for Kessel.

It truly is unfortunate the circumstances under which Phil Kessel came to Toronto. If not for the price causing the fanbase agony for years following, Kessel is likely a much more beloved figure. It’s easy to forget that Kessel scored at a 30 goal pace each of his first five seasons with the Toronto Maple Leafs and didn’t miss a single game after making his debut.

In a normal situation, that makes a player loved in a city. For Kessel and Toronto, it could never just be “normal”.

Toronto Maple Leafs goaltender Andrew Raycroft . (Photo by Jay Gula/Getty Images) /

The Fleecing

Date: June 24, 2006

Leafs Acquire: Andrew Raycroft

Bruins Acquire: Tuukka Rask

For most of the trade history between these two franchises, the biggest steal was the Toronto Maple Leafs getting Ian Turnbull out of a 44-year-old Jacques Plante. Yet on Draft Day 2006, John Ferguson Jr. somehow made a worse deal.

Simply put, it’s unfathomable how bad this trade is. Any and all justifications for the trade never made sense, whether the day of the trade or 14 years later.

When the trade was made, Andrew Raycroft was two years removed from his Calder winning season, an award he won at the advanced age of 23. His 2005-06 season was atrocious, seeing his save percentage drop from .926 in his Calder winning year to a .879.

Raycroft allowed 18.64 more goals than average in just 30 games. Tim Thomas had a .917 SV% that year. Even Hannu Toivonen, a 21-year-old rookie, had a .914 SV%.

Despite all of the signs pointing towards it being a bad decision, JFJ decided that trading one of the top goaltending prospects league-wide was a good idea.

Rask was one year removed from being drafted in the first round and was fresh off of a stellar performance at the World Juniors. At just 18 years of age, Rask had put up a .926 SV% in the Finnish Liiga. All the signs pointed towards him becoming a number one goaltender in the NHL.

Justin Pogge was the other top goaltending prospect Toronto had. In having two high-end prospects in net, part of the justification of the trade was that the Leafs could find a fix in net in the short term while still holding onto a future starter down the road.

That being said, Pogge was undoubtedly a lesser prospect than Rask. He was a later pick having been drafted in the third round and was a year older than Rask, though he did have a similarly excellent World Juniors and had also put up a .926 SV% in the WHL.

Pogge was a good prospect, but Rask was a great prospect. For reference, Rask was ranked the 37th best prospect in The Hockey News’ 2006 Future Watch, while Pogge was 73rd. Rask was the fifth overall goaltender, Pogge was 10th.

From Day One this trade was a terrible idea.

It’s stunning how poorly managed the Leafs used to be. Multiple goaltenders were on the market, Raycroft had become the Bruins third-string goaltender, and interest in him reportedly peaked around a second-round pick. Toronto still decided it was best to offer such a high-level prospect.

We all know how this one played out too.

Raycroft, shockingly, never found his 2003-04 form again. Although he played 72 games for Toronto in 2006-07, he was still a sub .900 netminder. By the start of 2007-08, he was already a backup, before leaving Toronto the following season.

Rask, on the other hand, made his debut that 2007-08 season. By 2009 he was a top-level goaltender, and after a few years backing up Tim Thomas, became one of the premier goaltenders in the NHL through 2020.

If John Ferguson Jr. had just been patient with the goalie market in 2006, the Leafs would’ve had their goaltending situation sorted for the past decade.

Instead, the decision to pay top level for a 25-year-old two years removed from his only NHL success led to the goaltending position being a question mark for the franchise for the same period of time.

Next. The 3 Most Important Signings Under Lamoriello. dark

Next time in the Toronto Maple Leafs trade history is another division rival in the Buffalo Sabres.

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