The 25 Best Trades in Toronto Maple Leafs History

This list is an attempt at a semi-objective ranking of best trades made by the Toronto Maple Leafs. It makes use of Hockey Reference’s Point Shares metric to rank the trades.

A Point Share is a player’s share of the points his team earns in the regular season. (There are numerous problems with Point Shares, some of which we have listed at the end of this list.)

In order to rank the trades we took the total Point Shares players acquired by the Leafs accumulated for the Leafs and then subtracted the Point Shares the players sent out from the Leafs accumulated for the other team in the trade. We included all trades since the franchise came into existence but please let us know if we missed any.

We did this calculation for only the franchises involved in the trade so Point Shares accumulated for other franchises later on in the career, or if a player returned to the team later, do not count. (Again, the problems with this approach are discussed at the end.)

By our estimation the Leafs have given up way more in regular season Point Shares than they’ve ever received in return. (Though they’ve made a lot of money!) We estimate that, through trades and the waiver wire, the Leafs have given up over 820 Point Shares more than they’ve received. Gretzky is the career leader in Point Shares at 251. So, basically, the Leafs have given up over 3 Gretzkys in terms of regular season wins over the course of the last 100 years.

So the list of best 25 trades is a bit of stretch. It was a lot easier to find the bad ones.

Here they are: the 25 best trades in Leafs history ranked by Point Shares.

All Point Share data as of December 30, 2019

Honourable Mentions:

• Bucko McDonald for Bill Thomson and cash – 20.1 PS
• Bernie Parent and a 2nd for Bruce Gamble, Mike Walton and a 1st – 20.1 PS

To start off we have two honourable mentions with a tie 26th at +20.1 PS

On December 19, 1938, the Leafs traded Bill Thomson and $10,000 for Bucko McDonald, a Red Wings defenseman in his 20s who had already won two Cups with the Wings.

McDonald would go on to win a third Cup with the Leafs – against the Wings – in 1942 and would be a 2nd Team All Star that year. He would play a total of 197 games for the Leafs, or parts of 6 seasons.

The Leafs had acquired Bill Thomson as a free agent but he hadn’t played for them at the time of the trade. He made it into a total of 9 games for the Leafs.

So we can view this as a pretty early example of the Leafs throwing their financial weight around to get what they want. It netted them 20.1 Point Shares and contributed to a Stanley Cup.

Then we have the time when the Leafs got Bernie Parent.

Parent had bounced around the league as a young backup goalie, playing for both the Bruins and the Flyers. A 3-team trade sent Parent and a 2nd round pick to the Leafs, while they gave up Bruce Gamble and a 1st to the Flyers and Mike Walton to the Bruins (by way of the Flyers).

Parent became Jacques Plante’s backup (see below). But the 2nd round pick turned into Rick Kehoe.

Bruce Gamble played 35 games for the Flyers. The Flyers used their pick on Pierre Plante, who would play 26 games for the Flayers. Oof.

Walton was technically traded to the Flyers first, and then to the Bruins. So we opted not to add his Bruins Point Shares to the trade. (It would be a virtual draw if they were included.)

But what keeps this trade from being one of the greatest in the history of the Leafs is what the Leafs did later: allowing Parent to go to the WHA and then, eventually, back to the Flyers – see our list of the Leafs’ 25 Worst Trades – and trading away Kehoe.

25. Tie: Babe Pratt for Garrett and Goldup / Yushkevich for Picks – 22 PS each

On November 27, 1942 the Leafs acquired Babe Pratt for Hank Goldup and Red Garrett.

Leafs get Babe Pratt – 27.1 PS (52G, 109A for 161P in 179 GP)

Rangers get:

• Red Garrett – 0.3 PS (1G, 1A for 2P in 23 GP)
• Hank Goldup – 4.8 PS (34G, 46A for 80P in 102 GP)

Pratt was a 27-year-old defenseman when the Leafs acquired him. He would play 179 games for the Leafs over 4 and a half seasons, winning the Hart and making one 1st and one 2nd end of season All Star Team. (Did he deserve the Hart? We have a podcast episode about that.)

Goldup had one good year for the Rangers and Garrett played one season.

Okay, next one: On August30, 1995, the Leafs acquired Dmitri Yushkevich and a 2nd in 1996 for multiple picks in the 1996 and 1997 drafts.

Leafs get:

• Dmitry Yushkevich – 26.1 PS (25G, 110A for 135P, -12 in 506 GP)
• 1996 2nd Round Pick – 0PS (0 GP)

Flyers get:

• 1996 1st Round Pick (Dainius Zubrus) – 4.2 PS (19G, 43A for 62P, +27 in 200 GP)
• 1997 2nd Round Pick (Jean-Marc Pelletier) – (0.1) PS (0-1-0, .828 SV%, 5.00 GAA, 0 SO)
• 1997 4th Round Pick – 0 PS (0 GP)

Yushkevich was a struggling young defenseman for Philadelphia. On the Leafs he eventually became a reliable minutes eater. (His Point Shares compared to Pratt’s show how much easier it was for ’90s players to amass point Point Shares compared to players in the ’40s, when the ’90s players aren’t even All Stars.)

The 2nd round pick the Leafs received didn’t amount to an NHL player.

With the 1996 1st, the Flyers drafted Dainius Zubrus. But Zubrus was a role player for the Flyers before being traded to the Habs in 1999.

The 1996 4th round pick didn’t amount to an NHL player.

And the Flyers’ 1997 2nd round pick played 1 NHL game for the Flyers before becoming a throw-in in the Brind’Amour deal.

24. Jacques Plante – 22.3 PS

Leafs get: Jacques Plante – 22.3 PS (48-38-15, .925 SV%, 2.46 GAA, 7 SO)

Blues get: Cash

Plante was 41 when he was traded to Toronto. But he had won the Vezina (when it was still the Jennings) in his age-40 season and helped lead the Blues to the final.

The Leafs were rich the Blues were not. So the Leafs paid the Blues.

Planted played over 100 games for the Leafs, posting a .925 save percentage and 2.46 GAA along with 7 shutouts.

23. Ullman for Mahovlich – 22.4 PS

Leafs get:

• Doug Barrie – 0 PS (0 GP)
• Paul Henderson – 33.8 PS (162G, 156A for 318P, +81 in 408 GP)
• Floyd Smith – 4.4 PS (25G, 34A for 59P, +19 in 131 GP)
• Norm Ullman – 43 PS (166G, 305A for 471P, +55 in 535 GP)

Red Wings get:

• Carl Brewer – 9.1 PS (2G, 37A for 39P, +43 in 70 GP)
• Frank Mahovlich – 24.2 PS (108G, 88A for 196P, +65 in 198 GP)
• Pete Stemkowski – 10.2 PS (51G, 63A for 114P, +12 in 170 GP)
• Garry Unger – 15.3 PS (84G, 68A for 152P, +1 in 216 GP)

On March 3, 1968 the Maple Leafs traded one of their best players, along with the rights to long-time Leaf Carl Brewer, role player Pete Stemkowski and prospect Garry Unger for Norm Ullman, one of the three best forwards on the Red Wings, as well as second liner Paul Henderson, role player Floyd Smith and prospect Doug Barrie.

It was a blockbuster trade motivated, in part, by Mahovlich’s struggles with depression.

Given what Mahovlich and Unger did for the remainders of their careers, it might seem like this trade would be a loss for the Leafs. But those guys had their greatest success on teams other than the Red Wings.

Norm Ullman was 32 when this trade happened and he had been one of the offensive stars for the Red Wings during the 1960s, along with Gordie Howe and Alex Delvecchio. But Ullman turned out to have excellent longevity and played in the NHL until he was 39, for the Leafs. For much of that time, he was the Leafs’ star player, bridging the gap between the Keon-Mahovlich era and the Sittler era. (Ullman would play in the WHA for a couple of seasons after the Leafs waived him.)

Paul Henderson had a good career for the Leafs – scoring 30 goals twice and 20 goals five times – at a time when they weren’t very good before departing for the WHA. (He also did something else you might have heard of.)

Floyd Smith played two seasons for the Leafs before being traded to Buffalo in 1970.

Doug Barrie was traded back to Detroit three months later for cash.

Mahovlich played nearly 200 games for Detroit before being traded to Montreal in early 1971. He would win 2 Cups with the Canadiens.

Garry Unger played over 200 games for the Red Wings as an emerging star before getting traded to the Blues in 1971, where he would play over 650 games and score nearly 300 goals. He would go on to set the record of consecutive games played while playing for the Blues.

Pete Stemowski would play in 170 games for Detroit, tallying 114 points, before being traded to the Rangers.

Carl Brewer returned to the NHL to play for the Red Wings for one season but then left the league again to work in the hockey equipment industry. When the Wings traded him to the Blues he returned for two more seasons. (He would later play in the WHA and rejoin the Leafs at 41.)

If the Red Wings hold on to Mahovlich and Unger, they win this trade in terms of Point Shares. But, because they didn’t, the Leafs got more productivity out of the players they got back.

22. Larry Hillman – 23 PS

Leafs get: Larry Hillman – 23 PS (13G, 75A for 88P, +30 in 264 games)

Bruins lose Larry Hillman – 0 PS

On June 8, 1960 the Leafs picked up Larry Hillman from the Bruins. So this is technically not a trade, as Hillman was claimed through the old interleague draft. However, as we pointed out at the outset, the Leafs haven’t had the greatest success in trading with other teams, so we’re cheating and adding waiver pick ups.

Hillman was 23 when the Leafs picked him up on waivers. He somehow had already played nearly 200 NHL games, though. (The ’50s were a different time…)

Hillman would play over 250 of his 789 NHL games with the Leafs, winning two Stanley Cups with them (in 1964 and 1967) and leaving the same way he game in, getting drafted in the interleague draft by the Rangers in 1968.

The Bruins got a roster spot out of it.

21. Getting Andreychuk – 23.5 PS

Leafs get:

• Dave Andreychuk – 23.9 PS (120G, 99A for 219P, +16 in 223 GP)
• Darren Puppa – 1.9 PS (6-2-0, .922 SV%, 2.26 GAA, 2 SO)
• 1993 First Round Pick (Ken Jonsson) – 7 PS (6G, 29A for 35P, +4 in 89 GP)

Sabres get:

• Grant Fuhr – 9.3 PS (25-29-5, .886 SV%, 3.60 GAA, 2 SO)
• 1995 Fifth Round Pick – 0 PS (0GP)

On February 2, 1993 the Leafs sought to improve their Cup chances by trading for life-long sabre Dave Andreychuk.

Andreychuk was having one of the best years of his career and instantly clicked with Doug Gilmour – Andreychuk would have the two best seasons of his career this season and the season after and he would never have another playoff performance like 1993 for the Leafs, with 12 goals in 21 games.

Puppa spent the rest of the season as Potvin’s backup and was lost in the Panthers expansion draft in the summer.

But the draft pick turned into Kenny Jonsson who became one of the Leafs best defensive prospects until he was traded to bring back Wendel Clark in a trade which made our other list of trades…

Fuhr was brought in to provide a veteran 1A for Dominik Hasek who, though 28, was not yet a star. However, in 1993-94 he became one and Fuhr became expandable – he was traded part way through the next season.

The Leafs pick didn’t result in an NHL player.

20. Jonathan Bernier – 24.5 PS

Leafs get: Jonathan Bernier – 28.2 PS (59-68-17, .915 SV%, 2.81 GAA, 6 SO in 151 GP)

Kings:

• Matt Frattin – (0.1) PS (2G, 4A for 6P, -6 in 40 GP)
• Ben Scrivens – 3.8 PS (7-5-4, .931 SV%, 1.97 GAA in 19 GP)
• 2015 Second Round Pick – 0 PS (later traded back to the Leafs visa Columbus)

On June 23, 2013 the Leafs traded for a goalie despite already having one. Some of us were not very happy about this trade given that the Leafs already had a goalie, however it is a good example of the Leafs using their wealth to take advantage of other teams, as the Kings were having trouble signing Bernier.

Bernier stole the starting job from Reimer initially but his play declined in subsequent seasons. He was eventually traded away for nothing after Reimer had already been traded away. But the Leafs got a lot more out of him than the Kings got out of this deal.

Scrivens had an excellent season as Jonathan Quick’s backup but was traded to Edmonton because Martin Jones was even better.

And Frattin was ineffective enough he was traded to Columbus that same season.

Leafs fans may not have been happy with Bernier, but this trade is a clear win.

19. Getting Rid of Wally Stanowski – 24.7 PS

Leafs get:

• Cal Gardner – 15.9 PS (58G, 95A for 153P in 220 GP)
• Bill Juzda – 15.4 PS (3G, 29A for 32P in 211 GP)
• Frank Mathers – 1.6 PS (1G, 3A for 4P in 23 GP)
• Rene Trudell – 0 PS (0 GP)

Rangers get:

• Elwyn “Moe” Morris – 0.8 PS (0G, 1A for 1P in 18 GP)
• Wally Stanowski – 7.4 PS (3G, 14A for 17P in 146 GP)

On April 26, 1948 the Leafs traded Stanowski, who was nearing 30, and depth defenseman Moe Morris for a bunch of players.

Gardner was a young centre for the Rangers who became an important depth centre for the Leafs, winning the Cup with them in 1949 and 1951.

Juzda was younger than Stanowski which may be why the Leafs wanted him in the trade. Like Stanowski he didn’t produce a lot but like Gardner he won two Cups with the Leafs.

Mathers actually played for the Leafs – he never played for the Rangers – but only intermittently, and he was never on a playoff roster.

Trudell was never able to make the Leafs.

Stanowski was considerably less dynamic offensively on the Rangers than he was on the Leafs, and it looks like the Leafs got out from under his contract at just the right time. (Stanowski produced .33 PPG for the Leafs and just .12 PPG for the Rangers.) Stanowski retired after his age 31-season.

After his incredible rookie year Morris was never a regular player again for the Leafs and even less so for the Rangers, and he was traded into the minors after 18 games.

So it’s hardly the biggest trade on this list in terms of names, but the Leafs got a fair amount back for very little.

18. A Pick for Jamie Macoun – 25.3 PS

Leafs get: 1998 Fourth Round Pick (Alexei Ponikarovsky) – 27.7 PS (114G, 143A for 257P, +25 in 477 GP)

Red Wings get: Jamie Macoun – 2.4 PS (1G, 10A for 11P, -1 in 76 GP)

At the March 1998 Trade Deadline, the Leafs trade Macoun for a 4th round pick, a seemingly inconsequential deal.

Macoun had played nearly 500 games for the Leafs but was soon to turn 37.

This trade may actually be viewed by some as a loss for the Leafs because the Red Wings would go on to win the Cup in 1998. But Macoun was a depth player on a team that swept the Capitals in the Finals. They were one of the favourites to win the Cup at the beginning of the season. Macoun would play one more season with the Wings before getting benched in the playoffs in 1999.

Meanwhile the Leafs pick turned into Alexei Poniarovsky who is 6th in scoring among Leafs for the aughts decade. Maybe that’s more of a testament to those Leafs not being very good, but it’s undeniable Ponikarovsky was a big part of those teams.

17. Van Riemsdyk for Schenn – 25.3 PS

Leafs get: James Van Riemsdyk – 35 PS (154G, 140A for 294P, -47 in 413 GP)

Flyers get: Luke Schenn – 8.9 PS (12G, 30A for 42P, -6 in 213 GP)

Count one of us as one of the many idiots who thought this was a mistake.

Luke Schenn was an up-and-coming stay-at-home defenseman for the Leafs, alternatively trusted and not by his coach. (21:32 ATOI, then 16:53, then 22:22 then 16:02 in his four seasons for the Leafs.)

Van Riemsdyk was a higher pedigree prospect, drafted the year before, but playing 3rd line minutes in far fewer games.

The Leafs were able to see the change coming and realized Schenn was too slow, whereas the Leafs could really use a garbage goal scorer.

The result: Van Riemsdyk co-lead the Leafs in points while he was on the team. The Leafs eventually let him go in free agency and he returned to the Flyers.

Schenn played as a depth D for the Flyers before being traded at the deadline to the Kings during his 4th season.

The Leafs were right to bank on a goal-scorer in the changing NHL rather than a guy who was meant for the Dead Puck Era.

Great trade.

16. Getting Wally Stanowski – 27.1 PS

Leafs get: Wally Stanowski – 26.9 PS (20G, 74A for 94P in 282 GP)

Americans get: Jack Shill – (.2) PS (1G, 3A for 4P in 25 GP)

On October 17, 1937 the Leafs traded Jack Shill, a depth defenseman they had already loaned to the Bruins, for the rights to Wally Stanowski who had yet to play a game for the Americans.

Stanowski finished 2nd in Calder voting his first season for the Leafs. He made the 1st All Star Team in his second season. And the Leafs won 4 Cups with Stanowski even with Stanowski missing time for World War 2. Oh, and on the 1942 team, Stanowski co-led the playoffs in assists.

So he had a pretty good career with the Leafs.

Shill played 25 games for the Americans before being sent to the minors.

15. Harry Watson – 27.9 PS

Leafs get: Harry Watson – 33.4 PS (163G, 122A for 285P in 500 GP)

Red Wings get: Billy Taylor – 5.5 PS (17G, 46A for 63P in 60 GP)

On September 21, 1946 the Leafs traded one of their best forwards, Billy Taylor, for the up-and-coming Harry Watson.

Watson would be be even better than Taylor, as he was 3rd in Points for the period he was on the Maple Leafs. During this time the Leafs won 4 Stanley Cups, though Watson was never the best player on these teams.

Watson was traded to the Blackhawks in late 1954, and he would retired after a couple of seasons playing for them.

Taylor actually had an excellent season for the Red Wings – he led the league in assists and set there record for most assists in a single game. But the Wings wanted to get younger so they traded Taylor to the Blackhawks for a young role player, Bep Guidolin, who would not make it to 300 points in his NHL career.

14. Red Kelly – 29.1 PS

Leafs get: Red Kelly – 31.1 PS (119G, 232A for 351P, +59 in 470 GP)

Red Wings: Marc Reaume – 2 PS (0G, 2A for 2P, -15 in 47 GP)

On February 10, 1960 the Detroit Red Wings traded their franchise defenseman – perhaps the player the Norris trophy was invented for – to the Maple Leafs for a younger player. (Reume was about to turn 26, Kelly was 32.)

The trade allegedly happened because of Kelly’s comments to the media about an off-ice issue he was having. Originally supposed to be traded to the Rangers, Kelly threatened to retire. So a trade to the Leafs was engineered instead.

What maybe made sense on paper ended up being a disaster for the Red Wings:

Kelly was famously moved to centre by the Leafs and became their #1 centre for much of the next decade. (He would share this role with Dave Keon.)

Reaume barely played for the Wings over the next two seasons and was basically unplayable. The Wings sent him to the minors. He would eventually play 30 more NHL games, 3 for the Habs in 1963-64 and 27 for the expansion Canucks in their inaugural season.

Ouch.

13. Darcy Tucker – 35.5 PS

Leafs get:

• Darcy Tucker – 32.3 PS (148G, 171A for 319P, -1 in 531 GP)
• 2000 Fourth Round Pick (Miguel Delisle) – 0 PS (0 GP)
• 2001 Fifth Round Pick Swap (Kyle Wellwood) – 8.8 PS (31G, 77A for 108P, -10 in 189 GP)

Lightning get:

• Mike Johnson – 5 PS (21G, 39A for 60P, -12 in 92 GP)
• Marek Posmyk – 0.6 PS (1G, 2A for 3P, 0 in 19 GP)
• 2000 Fifth Round Pick (Pavel Sedov) – 0 PS (0 GP)
• 2000 Sixth Round pick (Aaron Gionet) – 0 PS (0 GP)
• Maple Leafs option to swap 2001 Fifth Round Picks (Terry Denike) – 0 PS (0 GP)

On February 9, 2000 the Lightning traded Darcy Tucker, an up-and-coming player they had received as a prospect from the Canadiens, for Mike Johnson.

One can see the logic: Johnson was a year younger and seemed equally competent at scoring. In addition, Tampa was getting 2 lottery picks for 1. They should have won the trade, right?

Well, Tucker found a role on the Leafs and became a major part of the Leafs for most of the next decade, including a team that went to the Eastern Conference Finals.

And only one of the many picks involved resulted in an NHL player, the pick the Leafs received in their right to swap 2001 fifths. That player was Kyle Wellwood, hardly a star but certainly a lot better than the other players in the deal (outside of Johnson and Tucker).

As for Tampa, they gave up on Johnson just over a season later, moving him at the 2001 Trade Deadline as part of the package for the goalie who would win them the Cup. (So I guess this worked out for them after all?)

And Posmyk couldn’t stick at the NHL level.

So, as long as we don’t follow the ripples too far, this trade is a clear win for the Leafs.

12. 2006 Pick Swap – 38.1 PS

Leafs get:

• 2006 Fourth Round Pick (James Reimer) – 36.9 PS (85-76-23, .914 SV%, 2.83 GAA, 11 SO)
• 2006 Fourth Round Pick (Korbinian Holzer) – 1.2 PS (2G, 7A for 9P, -10 in 58 GP)

Blackhawks get: 2006 Third Round Pick (Tony Lagerstrom) – 0 PS (0 GP)

The Leafs apparently didn’t have anyone they wanted to draft in the 3rd round of the 2006 NHL entry draft, so they traded down for two 4ths. It’s not every day a trade like this works out this well.

Reimer famously became the Leafs’ goaltender of the future. Until he wasn’t. He starred in his first season – stealing the starting job from “The Monster” and Giguere – and again stealing the starting job in his third season. But his inconsistent play led the Leafs to look for his replacement. (See #20 on this list.) Eventually, he was traded away for a goon in a trade that would have made our Top 40 Worst Trades in Maple Leafs History if we decided to go that far.

Holzer never managed to stick with the Leafs, but still played games in the NHL.

Lagerstrom, on the other hand, never made it over from Sweden.

Sometimes seemingly inconsequential deals make a big difference.

11. King Clancy – 38.6 PS

Leafs get: King Clancy – 39.7 PS (52G, 78A for 130P in 286 GP)

Senators get:

• Eric Pettinger – (0.6 PS) (0P in 13 GP)
• Art Smith – 1.7 PS (2G, 4A for 6P in 43 PS)
• $35,000

On October 11, 1930 the Leafs traded two role players and money for King Clancy.

At 27, King Clancy was one of the best players of the 1920s. He was one of the most productive defenders in the league – having led the league in assists in 1923-24 – and he was also well-regarded league wide, having three Top 5 finishes in Hart voting while with the Senators, and one other Top 10 finish.

Ottawa was the smallest market in the NHL and they were struggling financially. So this trade was basically all about the money it brought back. (Reports say Clancy was essentially sold.)

And that makes sense because the hockey reasons for the trade seem nonexistent. Clancy was in his prime. Pettinger and Smith were basically checkers for the Leafs, scoring at rates of 0.13 and 0.19 PPG respectively. (Clancy, a defenseman, scored at .51 PPG per game for the Senators.)

And the results of the trade were predictable: Clancy continued his Hall of Fame career with the Leafs, finishing Top 5 in Hart voting twice more, and making two 1st and two 2nd end of year All Star Teams. In the playoffs, he helped the Leafs to a Stanley Cup in 1932 (his third).

Pettinger played 13 games for the Senators before he was sold to a minor league team. (But of course.)

Smith managed one full NHL season for the Senators.

The Senators became the St. Louis Eagles a few seasons later, and that lasted 1 season before the franchise was reabsorbed into the league.

10. Beauchemin for Lupul et al. – 39.1 PS

Leafs get:

• Jake Gardiner – 40.6 PS (45G, 200A for 245P, +9 in 551 GP)
• Joffrey Lupul – 20.7 PS (88G, 94A for 182P, -333 in 280 GP)
• 2013 Fourth Round Pick (Fredrik Bergvik) – 0 PS

Ducks get: Francois Beauchemin – 22.2 PS (32G, 59A for 91P, +44)

Beauchemin was signed by the Leafs to be their #2 or #3 defenseman behind Phaneuf and maybe Kaberle, but it didn’t really work out. No longer playing behind bother Niedermayer and Pronger it appeared that Beauchemin was not able to handle the same minutes he had in Anaheim.

So he was traded back to Anaheim on February 9, 2011 for a Top 6 winger, a prospect the Leafs’ GM had drafted when he worked for the Ducks, and a pick. And it worked out pretty well for both teams, but better for the Leafs.

Lupul had instant chemistry with Phil Kessel and had by far the best stretch of his NHL career until he finally succumbed to his perennial injury problems.

After some hemming and hawing by coaches and management, Jake Gardiner became one of the Leafs’ best defensemen. (Some believed he was the Leafs’ best defenseman for a while, but was just never played like it.) He was allowed to leave in free agency in 2019.

The 4th round pick didn’t amount to anything.

Beauchemin’s return to Anaheim resulted in the best seasons of his career, including a Top 5 Norris vote.

Win-Win, except the Leafs got two players and a draft pick out of it and the Ducks got a player.

9. Frederick Andersen – 42.8* PS

Leafs get: Frederick Andersen – 46.6 (131-62-32, .916 SV%, 2.77 GAA, 11 SO)

Ducks get:

• 2016 First Round Pick (Sam Steel) – 2.1 PS (10G, 20A for 30P, -7 in 74 GP)
• 2017 Second Round Pick (Maxime Comtois) – 1.5 PS to date (7G, 11A for 18P, -1 in 39 GP)

On June 20, 2016 the Leafs sought to fortify their goal-tending trading a 1 and a 2nd for the Ducks’ 1A goalie.

Andersen instantly became the Leafs’ #1 goalie and, though he is in the midst of the worst season of his career this year, he has still been the Leafs’ undisputed #1 for years now. He also had a pretty decent playoff in 2019.

Though Steel and Comtois are both very young players, they are so far only role players, especially Comtois. Though it’s possible one or both turn into Top 6 players in the future, until they do this trade will firmly be a Leafs’ win.

8. Bryan McCabe – 47.3 PS

Leafs get: Bryan McCabe – 55.2 PS (83G, 214A for 297P, +63 in 523 GP)

Blackhawks get:

• Alexander Karpovtsev – 7.9 PS (7G, 39A for 46P, -19 in 182 GP)
• 2001 Fourth Round Pick – 0 PS (0GP)

On October 2, 2000 the Leafs traded Karpovtsev – who they had received for Mathieu Schneider two years earlier – and a 4th for Bryan McCabe, a younger player a the same position who had begun to bounce around the league after being named the youngest Captain in Islanders history.

McCabe had by far the best years of his career in Toronto, as the #1 or #2 defenseman on the team for the majority of his 500+ games for the franchise. As part of that stretch, the Leafs made it to the Eastern Conference Finals with McCabe playing nearly 30 minutes a game.

Karpovtsev played Top 4 minutes for Chicago but was let down by injuries, eventually getting traded to the Islanders, McCabe’s first team.

The 4th rounder amounted to nothing.

A big win for the Leafs.

7. Stanley for Morrison – 52.3 PS

Leafs get: Allan Stanley – 58.6 PS (47G, 186A for 233P, +122* in 633 GP)

Bruins get: Jim Morrison – 6.3 PS (8G, 19A for 27P in 84 GP)

On October 5, 1958 the Leafs traded Jim Morrison for Allan Stanley.

Stanley had starred for bad teams for his entire career when the Leafs acquired him in his early 30s. (Stanley had finished 2nd in Calder voting in his rookie season but had avoided awards since.)

Maybe the Bruins thought Stanley was on the decline but how wrong they were: Stanley would finish 2nd in Norris voting twice for the Leafs, making three 2nd All Star Teams in his 633 games. And, of course, he would help the Leafs to four Stanley Cups.

The Bruins were likely banking on Morrison’s youth, as he was almost a half decade younger than Stanley. However, they would give up on him after barely more than a full modern season, trading him to Detroit for Nick Mickoski.

A huge win for the Leafs, especially given Stanley’s age at the time.

6. Ted Kennedy – 53 PS

Leafs get: Ted Kennedy – 59.4 PS (230G, 330A for 560P in 696 GP)

Canadiens get: Frank Eddolls – 6.4 PS (5G, 9A for 14P in 57 GP)

On September 10, 1943 the Maple Leafs acquired the rights to 17-year-old centre Ted Kennedy from the Canadiens for the rights to 22-year-old defenseman Frank Eddolls.

The reasons for the trade are long, complicated and involve a personal intervention by Nels Stewart. Basically Kennedy signed with the Habs who did not treat him how he and his family expected to be treated and he did not want to play for them. Apparently he was threatened with getting blackballed from the NHL but he refused to join the team anyway. Eventually Nels Stewart convinced the Leafs to acquire him. Read the full story on Wikipedia.

Kennedy would win the Hart Trophy for the Leafs in 1954-55 – though this is a questionable win – and finish Top 2 in voting in 1950, and Top 5 the next year and in 1952-53. He was also named to three 2nd All Star teams. Kennedy won five Cups with the Leafs, leading the playoffs in points once, goals twice and assists once.

Frank Eddolls finished 4th in Calder voting his first season. In subsequent seasons they couldn’t find a role for him so they threw him into a trade with the Rangers in the 1947 off-season.

So, for mostly non-hockey reasons, the Leafs acquired their franchise centre for a decade for a reserve D. Oops.

5. “The Largest Trade in NHL History” – 53.4 PS

Leafs get:

• Doug Gilmour – 44.1 PS (131G, 321A for 452P, +55 in 393 GP)
• Jamie Macoun – 22.6 PS (13G, 88A for 101P, -37 in 466 GP)
• Kent Manderville – 2.7 PS (8G, 15A for 23P, -5 in 136 GP)
• Ric Nattress – 1.1 PS (2G, 14A for 16P, -1 in 36 GP)
• Rick Wamsley – (0.8) PS (4-6-0, .864 SV%, 4.29 GAA, 0 SO)

Flames get:

• Craig Berube – (1.7) PS (5G, 12A for 17P, -9 in 113 GP)
• Alexander Godynyuk – 1.9 PS (3G, 5A for 8P, +4 in 33 GP)
• Gary Leeman – 0.8 PS (11G, 12A for 23P, -6 in 59 GP)
• Michel Petit – 7.6 PS (8G, 40A for 48P, +2 in 134 GP)
• Jeff Reese – 4.7 PS (17-6-3, .883 SV%, 3.39 GAA, 1 SO)

On January 2, 1992, the Flames traded Doug Gilmour and four other players to the Maple Leafs for five players, the largest trade in NHL history. Gilmour had walked away from the Flames the day before, in protest of an arbitration award that summer he felt was unfair. This is the most common explanation for why the Flames got what they got.

Gilmour, of course, instantly became the star of the Maple Leafs. As a Maple Leaf he would lead the team to two straight Conference Finals – the first time in a decade and a half – he would win the Selke, finish Top 2 in Hart voting one year and Top 4 in another, and finish Top 2 in Selke voting one other time and Top 5 two other times. Gilmour’s performance in the 1993 playoffs remains the most dominant in the team’s history. Gilmour was traded 5 years later, in his early 30s, when the team was trying to build around new franchise centre Mats Sundin.

Macoun became an important part of the Leafs’ blueline during the Gilmour years. His +/- is dragged down by some really bad Leafs seasons right before he was trade to the Red Wings in 1998, where he would win a Cup.

Manderville began his career in Toronto as a role player. He was traded to the Oilers in late 1995.

Nattress finished the season for the Leafs and became a free agent.

Wamsley was disastrous as a backup in Toronto and retired after the 1992-93 season.

Berube, a goon, did his thing for a little while in Calgary, but he was traded to Washington a year and a half later. He would play for the Flames again at the end of his career.

Godlynyuk didn’t turn out to be any more of a prospect in Calgary as he was in Toronto. The Flames left him exposed in the Panthers’ Expansion Draft.

For the Flames, the trade hinged around Gary Leeman rediscovering his 1989-90 form, a season when he scored 50 goals. He did not. He was traded just over a year later to the Habs.

Petit was a role player on the Leafs and a role player on the Flames. He left as a free agent in 1994 having somehow amassed the most Point Shares of any player the Flames received in this trade.

Reese served as a capable backup to Mike Vernon for a little under two seasons, then he was traded to Hartford.

This trade likely makes it to the #1 spot in a lot of fans’ minds, as it feels like one of the most lopsided trades in NHL history. One reason it is not higher up on this list is that Point Shares weigh goals more than assists, so player like Gilmour, scoring 452P in less than 400 games, gets fewer Point Shares than a player like, say, Dave Andreychuk doing the same. (And, of course, Andreychuk never scored at that rate in his career. He’s just an example of a score-first player. If Gilmour’s Goals to Assists ratio was flipped on its head, Gilmour would have a lot more Point Shares, is the, um, point.)

Another reason is that the best players the Leafs got moved on before the end of the decade.

Still, one of the best trades in team history.

4. Vaive for Tiger – 58.4 PS

Leafs get:

• Bill Derlago – 23.6 PS (158G, 176A for 334P, -61 in 378 GP)
• Rick Vaive – 44.7 PS (299G, 238A for 537P, -68 in 534 GP)

Canucks get:

• Jerry Butler – 0.6 PS (19G, 20A for 39P, -8 in 128 GP)
• Tiger Williams – 9.3 PS (83G, 82A for 165P, -19 in 312 GP)

On February 18, 1980, the Leafs traded fan favourite Dave “Tiger” Williams and a role player as part of Harold Ballard’s tear-down of the Leafs for two young prospects, Rick Vaive – who had a good year in the WHA before getting off to a poor start with the Canucks – and Bill Derlago, a slightly older player having slightly more success but still not much.

Derlago became an important part of some bad Leafs teams during the ’80s, leading the team in assists one season. Derlago was traded to the Bruins in 1985.

Vaive, of course, became one of the greatest goal scorers in Leafs history, finishing one goal shy of 300 goals with the franchise, which put him 4th All Time when he was traded to Chicago in 1987. (He is now 5th All Time.)

Williams had a career best season in 1980-81 and led the playoffs in PIM in 1982, if that floats your boat, but he never again reached those heights. The Leafs sold high on Williams, actually, as he was in the middle of a career year when this trade happened. Sure, he exceeded it the next season but his PPG for Vancouver is lower than that with the Leafs, while the scoring league-wide went up. He was traded to Detroit in the 1984 off-season.

Butler was a slightly better PPG player for the Canucks than the Leafs but he left as a free agent in the 1982 off-season.

3. Plante for picks – 60.3 PS

Leafs get:

• 1973 1st Round Pick (Ian Turnbull) – 59.4 PS (112G, 302A for 414P, +26 in 580 GP)
• Future considerations (Eddie Johnston) – 4.3 PS (12-9-4, .894 SV%, 3.09 GAA, 1 SO)

Bruins get:

• Jacques Plante – 2.2 PS (7-1-0, .927 SV%, 2.00 GAA, 2 SO)
• 1973 3rd Round Pick (Doug Gibson) – 1.2 PS (7G, 18A for 25P, +7 in 52 GP)

On March 3, 1973, the Leafs traded Plante – who had been an excellent 1A for them for 2+ seasons (see above) – and a pick for a pick and future considerations. Plante was in his mid 40s at the time.

The Leafs used the pick on Ian Turnbull, who became the #2 D on the best Leafs teams in a decade. Turnbull played 9 seasons for the Leafs – leading that Conference Finals team in scoring – before being traded to the Kings in 1981 as part of Ballard’s destruction of the team.

Johnston was old, though not as old as Plante, and was not a success as a backup. He was traded to the Blues a year later.

Plante finished the season for the Bruins but accepted a job to coach the Nordiques in the WHA that summer, retiring for the second time. (He would eventually play in the WHA in his age-46 season.)

Doug Gibson made the Bruins and had a decent year as a role player but he was waived a year or so later.

The success of this trade hinges entirely on the Leafs nailing the pick they received for Plante but, given his age, it was hardly a risky move.

2. Clark for Sundin – 98.1 PS

Leafs get:

• Garth Butcher – 2.1 PS (1G, 7A for 8P, -5 in 45 GP)
• Mats Sundin – 114 PS (420G, 567A for 987P, +99 in 981 GP)
• Todd Warriner – 4.8 PS (36G, 48A for 84P, -12 in 253 GP)
• 1994 1st Round Pick – 0 PS (0 GP)

Nordiques get:

• Wendel Clark – 2.6 PS (12G, 18A for 30P, -1 in 37 GP)
• Sylvain Lefebvre – 20 PS (11G, 61A for 72P, +71 in 351 GP)
• Landon Wilson – 0.2 PS (2G, 2A for 4P, +4 in 16 GP)
• 1994 1st Round Pick – 0 PS (0 GP)

For reasons that elude us, there are still some fans who think the June 28, 1994 blockbuster of Wendel Clark et al. for Mats Sundin et al. was somehow bad for the Leafs. Blame it on hockey xenophobia because, at least by regular season Point Shares for the participating teams, this is the Best Trade in Toronto Maple Leafs History that involved players going both ways.

Butcher was a throw-in and retired after the Leafs released him after one season.

The goal of the trade was Nordiques’ rising star Mats Sundin. The trade made Sundin the new franchise player, eventually making the much older Doug Gilmour expendable. With Sundin on the team, the Leafs would make it to two Eastern Conference Finals and have a number of their best regular seasons (by wins or points). Sundin would also become the franchise leader in Goals, Points, Goals Created and Offensive Point Shares. The reason our method favours Sundin over Gilmour is because Sundin played 73% of his career with the Maple Leafs because of this trade, whereas Gilmour did not. And Sundin scored more goals, of course.

Warriner was even younger than Sundin. He was a role player for the Leafs for parts of 6 seasons until he was traded for a pick in 1999.

The pick the Leafs received was sent to Washington in a different trade.

One reason the trade was so successful for the Leafs by the Point Share metric is that Clark lasted one strike-shortened season with his new team. He was traded to the Islanders by the Avalanche before they played their first game. Clark’s PPG for that one season is lower than Sundin’s for his entire Leafs career by a whole .2 PPG.

Lefebvre had a much better experience, sticking with the franchise for five seasons and winning a Stanley Cup.

Wilson, the prospect Quebec received in the trade, was traded away in November 1996.

The pick Quebec received did not result in an NHL player.

By regular season Point Shares, this trade is, hands down, the biggest win for the Maple Leafs since expansion.

1. Broda for $8,000 – 120.4 PS

Leafs get: Walter “Turk” Broda – 120.4 PS (304-222-102, 2.53 GAA, 61 SO in 629 GP)

Red Wings get: $8,000

Maybe this is cheating, but it was an actual trade: Broda was playing for the minor league Detroit Olympics on May 6, 1936, but his NHL rights were owned by the Red Wings when the trade was made. Detroit was willing to make this deal because they already had three NHL goalies ahead of Broda on the depth chart.

$8,000 may have been a lot of money in 1936 but it worked out extremely well for the Leafs. In addition to starting for the Leafs for the next 12 years, Broda also led the team to five Stanley Cups, led the playoffs in GAA four times and led the playoffs in Shut Outs six times. And in the regular season he won two Vezinas (i.e. two modern Jennings), made two 1st All Star Teams and one 2nd, and finished in the Top 5 in Hart voting once. He also appeared in four All Star Games.

He is 44th All Time in goalie Games Played, 33rd All Time in Wins,19th in Ties (and OT/SO Losses) and 17th in Shut Outs. His GAA puts him at 43rd All Time but when adjusted for era he is 21st.

Not bad for less than $10,000.

Methodology:

This ranking relies on Hockey Reference’s Point Shares metric. That metric is flawed in many ways. Here is a brief list:

• Point Shares are an an approximation of individual value based upon team goal differential, as such they are flawed in the same way Plus/Minus is flawed. But they have been calculated back before goal individual goal differentials were tracked by the league, so they are even more flawed prior to the existence of this date. You can read about how they are calculated here. (Also, Time on Ice wasn’t tracked until the late 1990s, which further skews older Point Shares.)
• Point Shares weigh goals more than assists. This isn’t necessarily an actual problem, but explains why players with way more assists than goals – such as Doug Gilmour – have fewer Point Shares than you might assume.
• Point Shares are a regular season stat so this ranking does not take into account playoff performance, which is a huge problem for a ranking like this, especially prior to expansion when the Leafs regularly won Cups.
• Modern players earn more career Point Shares than older players because the seasons are longer now but also because more team points are awarded than ever before.

This ranking has additional issues by relying on Point Shares as the guiding metric:

• Totaling Point Shares completely ignores context. The team getting back fewer Point Shares in terms of regular season player performance might be better off is some way not captured by Point Shares:
  • Money in the trade allows the team to sign or pay another player;
  • Roster/Salary Cap Space allows the team to sign or pay another player;
  • Intangible chemistry/culture issues could be addressed by the trade;
  • In the free agency era, a player in the trade may have been planning to leave for free agency after the trade, anyway.
• Totaling Point Shares ignores what the teams did next. Specifically, if a team involved in the trade trades away or waives one or more of the players in the trade immediately, the trade may look worse for them than it actually was in reality (and better for the other team). For example, using Point Shares to calculate the impact of the Bruins-Leafs Phil Kessel trade makes it look like less of a loss for the Leafs because the Bruins traded away the players they got back before they got back before they could accumulate more Point Shares. So this is a first degree evaluation. (If you would like us to make a list with 2nd or 3rd degree or greater evaluations, let us know in the comments.)