31 Worst Toronto Maple Leafs Trades Ever

For our list of the Top 25 Best Trades in Toronto Maple Leafs History, we used Hockey Reference’s Point Shares, an attempt to value a player’s contribution to team points won. (You can read about it at in the Top 25 list.)

The cut off for that list 22 net Point Shares, though we included some honourable mentions at just over 20 net Point Shares.

Because, by net Point Shares, there have been a few more bad trades in Leafs history than good ones, this list is longer.

All Point Share data as of March 11, 2020

31. Max Bentley – (21) PS

Leafs get:

  • Max Bentley – 29.5 PS (122G, 134A for 256P in 354 GP)
  • Cy Thomas – 0.2 PS (1G, 2A for 3P in 8 GP)

Black Hawks get:

  • Gus Bodnar – 18 PS (87G, 142A for 229P in 399 GP)
  • Ernie Dickens – 7.6 PS (9G, 39A for 48P in 253 GP)
  • Bob Goldham – 6.1 PS (5G, 29A for 34P in 165 GP)
  • Bod Poile – 5.1 PS (23G, 29A for 52P in 58 GP)
  • Gaye Stewart: 13.9 PS (70G, 66A for 136P in 178 GP)

On November 2, 1947 the Leafs traded five players for Max Bentley and some guy. In fairness to the Leafs, this trade only makes our list because Point Shares are a regular season stat. Any team stat taking into account playoff wins would heavily favour the Leafs.

That’s because Bentley was great for the Leafs, helping lead the Leafs to three Stanley Cups, leading the playoffs in points one of those seasons and assists in another. He also finished top 5 in Hart voting on last time, the season he was traded. (He won the Hart for the Black Hawks two seasons before, hence why the Leafs traded five players for him.)

Cy Thomas couldn’t maintain a spot in the NHL and went to play in minor pro and senior leagues.

Bodnar had a decent stretch with the Hawks as the second or third centre on a bad team. He was traded to the Bruins in 1954.

Ernie Dickens was a fourth liner for the Hawks for a few years before going to the minors.

Bob Goldham played a few seasons for the Hawks before lucking out and getting traded to the Red Wings in 1950 where he would win three more Cups. (He won one with the Leafs.)

Bud Poile was only briefly on the Hawks but he was a 2nd Team All Star. He was traded to Detroit less than a year after being traded to the Hawks.

Gaye Stewart made that same 2nd All Star Team with Poile and was one of the Hawks’ better players before we too was traded to the Wings in the same trade as Goldham.

Yes, by the conventional “team who gets the best player in the trade wins” wisdom, there is no way this trade is a loss for the Leafs. But the Leafs gave up two All Stars, two regular NHLers and a roll player for one #1 centre – who only once led the team in points during the regular season – and a AAAA player. It doesn’t quite make sense.

30. Phil Kessel – (23.2)* PS

Leafs get:

  • Scott Harrington – 1.6 PS (0G, 1A for 1P, 0 in 15 GP)
  • Kasperi Kapanen – 7.8* PS (41G, 49A for 90P, +6 in 202 GP)
  • Nick Spaling – (0.3) PS (1G, 6A for 7P, -7 in 35 GP)
  • Conditional 2016 1st Round Pick (Sam Steel) – 0 PS (0 GP)
  • 2016 3rd Round Pick – 0 PS (0 GP)

Penguins get:

  • Tyler Biggs – 0 PS (0 GP)
  • Tim Erixon – 0 PS (0 GP)
  • Phi Kessel – 32.3 PS (110G, 193A for 303 GP, -11 in 328 GP)
  • Conditional 2016/2017 2nd Round Pick – 0 PS (0 GP)
  • Cash.

No, not that Phil Kessel trade. The other one.

The jury is still out on the trade which sent Phil Kessel and spare parts to the Penguins for prospects on July 1, 2015, but it’s not looking good so far.

Scott Harrington played a few games for the Leafs and some more for the Marlies before being traded to Columbus the next summer.

Kasperi Kapanen, the centrepiece of the deal, is currently one of the LWs on the Leafs who float around through the lineup because the leafs have no LW depth. He is a serviceable NHL player who is young enough he have a little more upside. He is not Phil Kessel.

Spaling was an extra forward on the Leafs for part of a season before he was moved at the trade deadline for an expiring contract and picks.

The 2016 1st Round Pick was traded to the Ducks before the 2016 draft.

The 2016 3rd Round Pick is still in college.

Tyler Biggs is in the ECHL.

Tim Erixon never made the Penguins and is now playing in Europe.

The conditional pick turned into Kasper Bjorkqvist, who played in the AHL this season.

But Kessel, Kessel had a hell of a stretch in Pittsburgh before he wore out his welcome. And one could make an argument that he should have won the Conn Smythe in 2016.

(Why isn’t the other Kessel trade on this list? Because Boston is stupid and traded Seguin and Hamilton early in their careers. So it doesn’t make the cut based on Point Shares for the Bruins.)

29. Cross for Modin – (23.6) PS

Leafs get:

  • Cory Cross – 9.2 PS (10G, 25A for 35P, +31 in 162 GP)
  • 2001 7th Round Pick – 0 PS (0 GP)

Lightning get: Fredrik Modin – 32.8 PS (145G, 141A for 286P, +16 in 445 GP)

On October 1, 1999 The Leafs traded younger winger Freddie Modin for older defenceman Cory Cross and a 7th Round Pick.

Cross was big and had been playing Top 4 minutes for a very bad Tampa team. He missed games regularly. For the Leafs, he never played a full season and never came close to playing the minutes he got in Tampa. He had one great playoff moment and he was allowed to leave as a free agent the next season (2002).

You’ll be shocked to learn that the 7th Round Pick did not turn into an NHL player.

Modin was about to turn 25. He soon fit into one of the Lightning’s two top lines and came in 3rd in playoff scoring for the team when they “won” the Cup in 2004. He was traded to Columbus after the lockout, leaving Tampa as its 5th All Time leading scorer. (He is no longer in the Top 10.)

28. 2011 6th Round Pick Swap – (24.4) PS

Leafs get: 2012 6th Round Pick – 0 PS (0 GP)

Ducks get: 2011 6th Round Pick (Josh Manson) – 24.2 PS (21G, 76A for 97P, +42 in 385 GP)

At the 2011 NHL Entry draft the Leafs decided they had too many picks and would rather have another one the next year. So they swapped their 2011 6th for another 2012 6th.

The Leafs drafted a player who made it into 57 AHL games before he was included in the Dion Phaneuf trade (the one with Ottawa). He was playing in the ECHL as of last season.

With their new pick, the Ducks drafted Josh Manson, a defenceman from Northeastern. Manson’s 82-game average is 4G, 16A for 21P, +9 in 19:58 minutes of average ice time. He is a positive Corsi player. Sure, hardly a star. but an actual NHL player.

27. Brian Bradley – (26) PS

Leafs get: a roster spot

Lightning get: Brian Bradley – 26 PS (111G, 189A for 300P, -56 in 328 GP)

Okay, we’re cheating.

The Leafs left Bradly exposed during the 1992 Expansion Draft. Bradley was 27. Though a centre, the Leafs were playing him on the wing, where he was less far down the depth chart. But, presumably, they thought they had better options in young players, or shipping out Bradley was part of the remaking of the team for this new era.

Either way, Bradley went on to be the first star in Lightning history, good stats on bad teams.

26. 2 Players for 3 Players and a Pick – (27.2) PS

Leafs get:

  • Dave Hutchison – 6.9 PS (5G, 21A for 26P, +36 in 110 GP)
  • Lorne Stamler – (0.6) PS (4G, 3A for 7P, -7 in 45 GP)

Kings get:

  • Scott Garland – 0 PS (0G, 1A for 1P, -4 in 6 GP)
  • Brian Glennie – 1.2 PS (2G, 2A for 4P, +2 in 18 GP)
  • Kurt Walker – 0 PS (0 GP)
  • 1979 2nd Round Pick (Mark Hardy) – 33.4 PS (53G, 246A for 297P, -112 in 589 GP)

On June 14, 1978 the Leafs traded three players and a 2nd round pick for two players. If the pick works out how it normally would have, this trade doesn’t make our list.

Dave Hutchison was a veteran D for the Kings and was the target of the trade. He played well for the Leafs but they moved on from him by January 1980.

Lorne Stamler was a fringe NHLer for the Kings who perhaps played too much for the Leafs when he was put in the lineup. He was left exposed in the WHA merger draft.

Scott Garland had a career year for the Leafs before the trade (if you ignore his awful minus) so it’s kind of a wonder he didn’t help bring back more. Tragically he died in a car accident about a year after the trade after only making it into 6 games for the Kings.

Glennie had a good career as a depth D for the Leafs. He retired after only 18 games with the Kings.

Kurt Walker was a fringe NHLer for the Leafs and never even played for the Kings, playing a little more AHL hockey before retiring.

Pretty inconsequential trade, right?

Trading away picks can be dangerous. Mark Hardy would consistently put up points for a bad Kings teams. From 1979-80 until his trade to the Rangers on in June 1988, no other King’s D scored as many points as Hardy. That minus is ugly but it’s easy to imagine him with better numbers on a better team. (Not the ’80s Leafs, probably.)

Without the Kings lucking into that pick, this trade doesn’t make it on the list.

25. Gray for Keeling – (27.7) PS

Leafs get: Alex Gray – (0.3) PS (0P in 7 GP)

Rangers get: Melville “Butch” Keeling – 27.4 PS (136G, 55A for 191P in 452 GP)

On April 16, 1928 the Leafs traded Butch Keeling for Alex Gray.

Alex Gray was a senior player the Rangers gave a chance to during his age 28 season. The Leafs must have seen something in Gray because Keeling was already outperforming Gray points wise, despite being six years younger.

Gray never scored for the Leafs while Keeling was the 5th leading scorer for the Rangers over the next decade, behind three Hall of Famers and Cecil Dillon.

Oops.

24. Bringing Back Wendel Clark (1st time) – (29) PS

Leafs get

  • Wendel Clark – 9 PS (50G, 33A for 83P, -16 in 125 GP)
  • Mathieu Schneider – 9.9 PS (18G, 38A for 56P, -11 in 115 GP)
  • DJ Smith – (0.1) PS (0G, 1A for 1P, -6 in 11 GP)

Islanders get:

  • Sean Haggerty – 0.1 PS (1G, 1A for 2P, 0 in 10 GP)
  • Darby Hendrickson – (0.1) PS (1G, 4A for 5P, -6 in 16 GP)
  • Kenny Jonsson – 43.4 PS (57G, 175A for 232P, -20 in 597 GP)
  • 1997 1st Round Pick (Roberto Luongo) – 4.4 PS (7-14-1, .904 SV%, 3.25 GAA, 1 SO

On March 13, 1996, with great fanfare, Wendel Clark returned to the Maple Leafs along with Mathieu Schneider. Slightly less than 2 years after the trade that changed the Leafs forever – which stands as our 2nd best trade in Leafs history – it felt as though the Leafs were gearing up for a long playoff run.

Clark was a former Face of the Franchise, of course, but had not managed to stick in Quebec, getting traded to the Islanders for Claude Lemieux. Clark’s return to the Leafs got off to a great start in the regular season – 15P in 13 games – but the playoffs were another story – 4P, -6 in 6 games. His next two seasons were marred by injuries – as usual – but saw the team get worse. He was allowed to leave in free agency in 1998.

Schneider’s offensive numbers declined a little with the Leafs but some of that was due to injuries and some of that to the team around him also getting worse. His rights were traded to the Rangers the same off-season that Clark was allowed to leave. Of course, he would play in the NHL for over a decade more.

D.J. Smith spent most of his Leafs’ career in the minors. He was traded to Nashville in 2002.

Sean Haggerty mostly played in the minors after the trade, until Nashville grabbed him off waivers in 2000.

In one of the strangest moments among these many trades we’ve discussed in these two posts, Darby Hendrickson was traded back to the Leafs in October.

Kenny Jonsson soon became the Islanders’ #1 D and was normally on the top pair through to the lockout.

Most infamously of all, the pick the Leafs gave up in this trade became future Hall of Famer Roberto Luongo. Fortunately for the Leafs (for this ranking anyway), the Islanders gave up on Luongo by 2000, in one of the worst trades of the decade.

Teams shouldn’t trade prospects and picks for veterans unless they’re really close to contending.

23. Creighton for Flaman – (30.9) PS

Leafs get: Dave Creighton – 0.2 PS (2G, 1A for 3P in 14 GP)

Bruins get: Fern Flaman – 31.1 PS (18G, 119A for 137P in 458 GP)

On July 20, 1954 the Leafs traded Fern Flaman for Dave Creighton.

Creighton was an inconsistent centre for the Bruins, managing good numbers one year and poor numbers the next:

  • 4P in 12 GP in 1948-49
  • then 31P in 64 GP
  • then 9P in 56 GP
  • then 37P in 49 GP
  • then 16P in 45 GP
  • and finally 40P in 69 GP the season before this trade.

The Leafs saw something in him but he got off to a terrible start in Toronto and they traded him for cash only 14 games into the season.

Flaman began his career with the Bruins but was traded to the Leafs in 1950. It was with the Leafs that the defensive defenseman blossomed, going to the All Star Game and winning a Cup. But his second stint on the Bruins went even better: he made three 2nd All Star Teams, and finished Top 3 in Norris voting three times and Top 5 a further two times.

Ouch.

21. (tie) Pettinger for Owen – (31.2) PS / Cash for Dave Trottier

Leafs get:

  • Eric Pettinger – 1.4 PS (7G, 12A for 19P in 67 GP)
  • Hugh Plaxton – 0 PS (0 GP)

Bruins get: George Owen – 32.6 PS (44G, 33A for 77P in 183 GP)

On January 10, 1929 the Leafs traded the rights to George Owen for Eric Pettinger and Hugh Plaxton’s rights.

Pettinger was younger than Owen but not so significantly. His 18 games for Boston were not impressive (0 points) but Pettinger had lit up a senior league the previous season. For the Leafs he didn’t do much except help fetch King Clancy in October 1930.

Plaxton was a an amateur player who had recently won Olympic Gold (14 points in 3 GP). He never played for the Leafs, instead remaining an amateur. His rights later expired and he was signed as a free agent by the Maroons in 1932. (He would play 17 NHL games.)

Owen was another amateur star. He had lived in Massachusetts for a long time and brought this trade about because he didn’t want to play in Canada. Owen’s career for the Bruins may have been brief but it was good. They won the Cup in 1930.


Leafs get: $15,000

Maroons get: Dave Trottier – 31.2 PS (120G, 112A for 232P in 435 GP)

Yes, we’re cheating again. This isn’t a normal trade.

Trottier signed with the Maroons after starring for the same 1928 Olympic Gold Medal team as Hugh Plaxton. (Trottier scored 1 more point.) But the signing was ruled to be ineligible and his rights were awarded to Toronto.

A few months later, the teams came to a compromise: Trottier for cash. Trottier had a good career for the Maroons over the next decade: he was a Top 5 offensive player in the NHL in 1932 and the Maroons won the Cup with him in 1935.

20. JP Parise for 5* Players – (31.3) PS

Leafs get:

  • Murray Hall – 0 PS (0 GP)
  • Duke Harris – (0.3) PS (0P, -4 in 4 GP)
  • Don Johns – 0 PS (0 GP)
  • Len Lunde – 0 PS (0 GP)
  • Ted Taylor – 0 PS (0 GP)
  • Carl Wetzel – 0 PS (0 GP)

North Stars get:

  • Milan Marcettea – 1 PS (7G, 15A for 22P, -14 in 54 GP)
  • Jean-Paul Parise – 30 PS (154G, 242A for 396P, -85 in 588 GP)

On December 23, 1967, the Toronto Maple Leafs and Minnesota North Stars made a 8-player trade somehow only featuring one player of consequence.

Murray Hall was a 27-year-old AAAA player who had been left exposed by Chicago in the expansion draft. He had played 17 games for the Stars. He played zero games for the Leafs.

Duke Harris was a minor leaguer who got NHL playing time due to expansion. Minnesota held on to him for 22 games before including him in this deal. He played 4 games for the Leafs.

Don Johns was an AAAA player Minnesota acquired for cash. He played 4 games for the Stars before this trade. He played zero games for the Leafs.

Len Lunde, though, had been an actual NHL player! Albeit earlier in the decade. He scored 28 points in 1963! By the time Minnesota claimed him in the draft, he was playing basically entirely in the minors. Lunde made it into 7 games for the Stars. Hep played zero games for the Leafs.

Taylor was among the youngest players in the trade but had been left exposed in the expansion draft. He did manage to play a whopping 31 games for the Stars before the trade. He played in zero games for the Maple Leafs.

What do all 5 of these players have in common? They were all on the Rochester Americans when they were sold to the new Vancouver NHL franchise. With that sale, the Leafs gave up every player they acquired in this deal to another team.

What about the last guy, Wetzel? He was “loaned” to the Leafs. Player loans happened a lot in the old days but they do not happen any more. We don’t know why he was in the trade, though he did play 10 games for the Americans before the sale of that franchise.

Milan Marcetta was a career minor leaguer in his age 31-season. He was included in this deal because, at bottom, it was a large swap of minor leaguers.

Parise had just failed to stick in the NHL. He played 21 games for the Bruins, scoring 4 points. He had made it into 1 game for the Leafs while putting up decent, but not eye-popping, numbers for the Americans. Parise had just turned 26. It’s easy to see why the Leafs didn’t see anything in him and didn’t think they were giving up much. Given the number of players the Leafs got back, it’s easy to see a rationalization that they were easily winning the deal. (Perhaps they needed more players on Rochester to sell the team.)

Instead, Parise was 2nd only to Bill Goldsworthy in scoring for the North Stars over the next 8 seasons.

19. Picks for Jason Smith – (31.4) PS

Leafs get:

  • 1999 4th Round Pick – 0 PS (0 GP)
  • 2000 2nd Round Pick (Kris Vernarsky) – 0 PS (0 GP)

Oilers get: Jason Smith – 31.4 PS (31G, 82A for 113P, +50 in 542 GP)

On March 23, 1999 the Leafs traded Jason Smith for a 2nd and a 4th.

The 4th Rounder was for that summer’s draft and it resulted in Jonathan Zion. Zion would never even make it in the AHL, playing way more games in the ECHL, before moving to Europe after the lockout.

The 2nd in the next draft resulted in Kris Vernarsky. The Leafs traded his rights in 2003 before he ever played a game for them.

Smith only became the Captain of the Oilers and led them to the Stanley Cup finals in 2006.

18. Reg Thomas for a pick – (31.6) PS

Leafs get: Reg Thomas – 0 PS (0 GP)

Oilers get: 1981 6th Round Pick (Steve Smith) – 31.6 PS (46G, 172A for 218P, +99 in 385 GP)

On August 22, 1979 the Leafs traded a 1981 6th round pick for Reg Thomas, a WHA 2nd liner whose rights who had just been acquired by the Oilers in the expansion draft.

Thomas couldn’t make the Leafs, which is not a surprise given that he was not a WHA star, and the Leafs shipped him to Quebec for two players in December. (The Leafs would re-sign him in the 1981 off-season but he still never played for them.)

A year and a half after the Leafs traded for Thomas, the Oilers used their pick on Steve Smith. Now, it’s likely a 6th Round pick in the hands of any other team at any other time likely would not have resulted in an NHL player – instead Steve Smith played over 800 NHL games.

17. Blaine Stoughton – (32.2) PS

Leafs get: a roster spot

Whalers get: Blaine Stoughton – 32.2 PS (219G, 158A for 377P, -59 in 357 GP)

On June 13, 1979 the Whalers claimed Stoughton, who was left unprotected, in the expansion draft. Stoughton had been acquired by the Leafs in 1974 – that trade is higher up on this list – but soon moved to the WHA. In his first season, he was a star but he struggled in future seasons, and experienced some injury trouble in his final WHA season.

That’s presumably why the Leafs left him unprotected. Because Stoughton tied for the league lead in goals in his first season for the Whalers, scoring 56 goals that season, 50 goals another time, 45 goals a total of three times and 40 goals a total of four times over the next half decade.

The Whalers traded him to the Rangers in 1984.

16. Larry Murphy – (32.3) PS

Leafs get: “Future considerations”

Red Wings get: Larry Murphy – 32.3 PS (35G, 136A for 171P, +56 in 312 GP)

Perhaps the most infamous Leafs trade of the last 25 years, the trade which sent Larry Murphy to the Detroit Red Wings for nothing on March 18, 1997 is extremely hard to understand now.

Murphy had just turned 36 but his numbers for the Leafs had not been bad, especially given the state of the team at the time: 19G, 81A for 100P, -1 in 151 GP. (Unfortunately we don’t have Murphy’s ice time for these games.)

The Leafs acquired Murphy for Mironov and a 2nd Rounder in the 1995 off-season – a trade which netted the Leafs 9.9 PS. But the Leafs were not great in 1995-96 – 14th out of 26 in the league in offense and defense – and they lost in the first round in 6 games. (Murphy’s stats in that series were bad: 2A, – 8.)

The next season, the Leafs were even worse, both offensively (17th) and defensively (21st) and Murphy became one of the fall guys.

For some reason, management let fan and media animus take control of their decision making and Murphy was traded for “future considerations” at the trade deadline. Those considerations never amounted to anything.

Then, Murphy helped the Red Wings win two Cups. His playoff stats for the Wings over this period? 7G, 27A for 34P, +33 in 67 GP, 21:49* ATOI (*non-Cup winning seasons only)

This may not be the worst trade in Leafs history by net PS, but it’s possibly the worst trade in Leafs history in terms of return.

15. Steve Sullivan – (34.6) PS

Leafs get: a roster spot

Black Hawks get: Steve Sullivan – 34.6 PS (118G, 185A for 303P, +54 in 370 GP)

Yes, we’re cheating again: On October 23, 1999, the Leafs waived 25-year-old Steve Sullivan, who was -1 with 1 assist in 7 games to start the season.

Sullivan had been acquired as as part of the Doug Gilmour trade – as was Jason Smith – and was mostly improving every season. But his poor start was apparently too much for Leafs management, which didn’t even try to trade him but instead tried to sneak him down to the minors. Oops.

Sullivan would go on to to be the best forward on the Blackhawks from the end of the century to the lockout – scoring 51 points more than any other Blackhawk during this period.

Sullivan was traded to Nashville for two draft picks at the 2004 Trade Deadline.

14. Cash for Lumley and Nesterenko – (36.3) PS

Leafs get: $40,000

Black Hawks get:

  • Harry Lumley – 0 PS
  • Eric Nesterenko – 36.3 PS (207G, 288A for 495P, +49* in 1013 GP)

On May 21, 1956 the Leafs sold the Black Hawks Harry Lumley and Eric Nesterenko.

Before playing for the Leafs, Lumley was the starter for the Black Hawks for two seasons and, before that, he was the starter for the Red Wings, where he won a Cup.

Lumley was the Leafs’ starter for the early ’50s, winning the Vezina (Jennings) in 1954 and finishing second in Hart voting in 1955. But in 1955-56 the Leafs tracked shots and Lumley’s numbers were not good as the Leafs barely made the playoffs.

Nesterenko was 22 but had failed to make the Leafs full time over 5 pro seasons.

Lumley refused to play for Chicago a second time and spent two bad years in the AHL before he was traded to Boston in early 1958.

But Nesterenko would become a core depth piece for the rising Black Hawks. He would win a Stanley Cup in 1961 and make it to three other finals over the next decade and a half. He was a massive dick, though.

The Leafs did get lots of money though, so it’s possible they didn’t really lose this one.

13. Pilote for Pappin – (39.3) PS

Leafs get: Pierre Pilote – 5 PS (3G, 18A for 21P, +5 in 69 GP)

Black Hawks get: Jim Pappin – 44.3 PS (216G, 228 for 444P, +86 in 488 GP)

On May 23, 1968 the Leafs traded 28-yea-old Jim Pappin for 36-year-old future Hall of Famer Pierre Pilote.

Pilote had played his entire career (821 GP) for the Black Hawks, winning three Norris Trophies, finishing second in voting three more times and finishing Top 5 two other times, making five 1st All Star Teams, and three 2nd Teams, and leading the Black Hawks to the Stanley Cup in 1961, when he was arguably the team’s MVP. A Hall of Fame career.

But in 1968, he was 36, coming off his lowest point total (37) since 1959 and his lowest +/- (-10) since the team began tracking the stat in 1960.

For the Leafs he was able to play most of the subsequent season but soon decided it was time to retire.

Pappin had a strange career for the Leafs: he was a role player for the Leafs in his mid-20s – he didn’t make the NHL until his age-24 season. Pappin spent the majority of the 1965-66 season, his 3rd NHL season, starring for the Rochester Americans in the AHL.

Then, in 1966-67, he scored 20 goals in the regular season (more than in the 101 NHL games he had played previously) and led the playoffs in goals and points on the way to winning the Cup.

As with many unlikely Stanley Cup heroes, Pappin soon had massive expectations, which he didn’t live up to in the 1967-68 season, though he was barely off his PPG pace of season previously.

So the Leafs moved on and Pappin played nearly 500 games for the Black Hawks, scoring 40 goals and 90 points in 1972-73.

He was traded to California in 1975.

12. Klukay for Boivin – (40.6) PS

Leafs get: Joe Klukay – 0.8 PS (8G, 9A for 17P in 74 GP)

Bruins get: Leo Boivin – 41.4 PS (47G, 164A for 211P, -139* in 717 GP)

On November 9, 1954 the Leafs traded 22 year-old defenseman Leo Boivin for LW Joe Klukay, who had just turned 32.

Klukay had a fine career for the Leafs in the late ’40s/early ’50s as a 2nd/3rd liner, contributing to 4 Stanley Cups. But they gave up on him in the 1952 off-season and traded him to Boston for cash.

Klukay went and had two of the best seasons of his career and so apparently the Leafs wanted him back, despite starting the season with a 10 game pointless streak. That streak was indicative of the state of Klukay’s game and he was sent down the minors the next season, after which re retired from professional hockey to play Senior.

Boivin had finished Top 5 in Calder voting in 1952-53 but apparently the Leafs were not willing to wait for him to develop and so traded him for a depth winger in his early ’30s.

With the Bruins, Boivin would finish Top 5 in Norris voting once, and help the team to two Stanley Cup finals.

The Bruins would trade Boivin to the Red Wings over a decade later and Boivin would eventually play 1150 regular season games and join the Hall of Fame in 1986.

11. Burrows for Carlyle – (41.6) PS

Leafs get:

  • Dave Burrows – 6.2 PS (5G, 27A for 32P, -17 in 151 GP)
  • 1978 6th Round Pick – 0 PS

Penguins get:

  • Randy Carlyle – 35.7 PS (66G, 257A for 323P, -100 in 397 GP)
  • George Ferguson – 12.1 PS (89G, 106A for 195P – 33 in 310 GP)

21st Century Leafs fans are no fan of Carlyle and you can count me among those who think his Norris Trophy is a joke. But that doesn’t mean the Leafs made a good trade on June 14, 1978 when they traded the 22-year-old defenseman and middle-6 forward George Ferguson for 29-year-old depth forward Dave Burrows and a low pick.

It’s hard to know what the thinking was here. Though Carlyle was unable to make the Leafs full-time in his first two NHL seasons, he was still very young with barely even a full NHL season under his belt and even fewer CHL games. (That’s CHL the minor league, not the junior league.)

Ferguson had put up 40 points twice in his Leafs career. He was far from a star but he was productive in his role, though it might have seemed at the time like his best days were behind him.

Dave Burrows had managed fewer career points to date than Caryle and Ferguson combined, despite being far older in hockey years than either player. Burrow’s career high was 29 points in 1975-76, one of only two seasons he managed to be a plus.

It makes no sense. None.

Burrows didn’t even manage to maintain his career 0.19 PPG average for the Leafs and he was traded back to the Penguins two years later.

The 6th round pick amounted to nothing.

Randy Carlyle won the Norris and made the 1st All Star Team in 1980-81, though you can argue that, as a -16 on the third worst defensive team in the NHL, he probably didn’t deserve it. (He also never had another Top 5 finish in Norris voting.)

Offensively he fared much better, scoring the 2nd most points of any Penguin over the next 6 seasons (nearly 50 points ahead of the next guy). He was traded to Winnipeg at the 1984 Trade Deadline.

Ferguson had the best seasons of his career for Pittsburgh. He was traded to Minnesota in 1982.

9. Tie: Stoughton for Kehoe / Gerry Cheevers – (41.9) PS

Leafs get:

  • Blaine Stoughton – 2.6 PS (29G, 25A for 54P, -10 in 121 GP)
  • 1977 1st Round Pick (Trevor Johansen) – 6 PS (4G, 21A for 25P, -13 in 132 GP)

Penguins get: Rick Kehoe – 50.5 PS (312 G, 324A for 636P, -82 in 722 GP)

Speaking of the Penguins robbing the Leafs: on September 13, 1974 the Leafs traded 23-year-old Rick Kehoe for 21-year-old Blaine Stoughton and a 1st.

On paper it looks smart: Stoughton was a higher draft pick than Kehoe, and younger, and the Leafs were getting him and a 1st Rounder.

But Stoughton bolted to the WHA after two seasons with the Leafs, the second of which saw him playing in the CHL (the minor league) for nearly half the season. When the WHA merged into the NHL the Leafs lost his rights to the Whalers (see #17 on this list)

The 1st Rounder ended up being 12th overall in a weak draft, which only produced two Hall of Famers and three 1,000 game players. (The real bad news is that Mike Bossy went 15th. Yes, the Leafs drafted a Junior B player over Mike Bossy. Let’s go Toronto!)

Rick Kehoe scored 272 more regular season points than anyone else on the Penguins over the next decade, including 55 goals in 1980-81 (4th in the league).

If the Leafs hadn’t screwed up with Stoughton, this trade likely looks like a wash, but they did.


Leafs get: a roster spot

Bruins get: Gerry Cheevers – 74.2 PS (226-103-76, .901 SV%, 2.89 GAA, 26 SO)

Cheating again: in the 1965 Intraleague draft the Leafs left left unprotected a 24-year-old minor league goaltender who had appeared in only 2 games for the Leafs back in 1961-62.

Cheevers got off to a rocky start in the AHL – at one point getting demoted to the Eastern Professional Hockey League – but he had just led the AHL in GAA. But the Leafs had two future Hall of Famers in net and other prospects in the pipeline.

Of course, Cheevers would go on to win two Stanley Cups with the Bruins, leading the playoffs in wins both of those runs, and leading the playoffs in total Shots Against, Saves and Shut Outs twice, and leading the playoffs in Minutes once before he bolted to the WHA.

Cheevers returned to the Bruins in 1976 but signed a new contract with Boston at the time, otherwise we’d included his Point Shares from those seasons too, and this decision would be 6th on this list instead of tied for 9th. (Cheevers also excelled in the WHA, winning its Vezina equivalent once and leading the league in Shutouts three out of four seasons.)

8. Cash for Flash Hollett – (50.9) PS

Leafs get: $16,000

Bruins get: Bill “Flash” Hollett – (50.9) PS – 84G, 115A for 199P in 353 GP

On January 15, 1936 the Leafs sold Flash Hollett to the Bruins.

Hollett was 24 but had got off to an uneven start with the Leafs. He was loaned to the Senators – yes that was a thing – after splitting part of his first NHL season between the NHL and IHL.

But he had a stellar second season for the Leafs, leading all Leafs D in scoring. Still, he was judged to be superfluous on a team that already included King Clancy and Red Horner and he was traded to the Bruins only 11 games into his 3rd NHL season.

The Bruins immediately sent Hollett to the minors while the Leafs went to the Stanley Cup finals.

However, Hollet would have an excellent career with the Bruins, making the 2nd All Star Team in 1943 and winning two Stanley Cups. Hockey Reference’s Defensive Point Share metric has him as the best D in the NHL in both 1937-38 and 1941-42 and he managed to somehow finish in the Top 10 in Goals 1941-42.

The Bruins traded Hollett to the Red Wings in January 1944.

7. Stempniak for Steen – (59) PS

Leafs get: Lee Stempniak – 4.3 PS (25G, 36A for 61P, -19 in 123 GP)

Blues get:

  • Carlo Colaiacovo – 20.8 PS (19G, 91A for 110P, +9 in 284 GP)
  • Alex Steen – 55.2* PS (195G, 301A for 496P, +50 in 765 GP)

And I (sort of) supported this at the time… (Despite being a big fan of Steen.)

On November 24, 2008 the Leafs traded the oft-injured, 25-year-old Carlo Colaicovo and the 24-year-old Alex Steen for 25-year-old Lee Stempniak, who had scored 27 goals in 2006-07 on a 16.3% shooting percentage.

Between injuries and minor-league assignments, Colaiacovo had never played more than 48 games in a season for the Leafs and so was no longer one of their top defensive prospects.

Steen, on the other hand had been playing a middle 6 role for three seasons and I have memories of his absolutely excelling during a Sundin injury one season. (I was biased.)

Stempniak was a 5th round pick getting Top 6 playing time on a bad Blues team. (Doug Weight had to pass to somebody.) He had 13 points in 14 games when the trade was made.

I (sort of) supported the trade at the time only because I thought the Leafs were screwing up Steen’s development and I wanted a clean break for him. (I think I also just wanted the team gutted so they would tank for high picks.)

Colaiacovo never played more than 67 games in a season for St. Louis but he gave them decent minutes when healthy. The Blues let him go in 2012 free agency.

Steen is now basically Mr. Blues. He leads the Blues in total points and games played since the trade, he scored 30 goals in 2013-14 and he won the Cup in 2019.

Stempniak put up 0.50 PPG during his brief time in Toronto, which is right on his career average.

He was traded to Phoenix at the 2010 Trade Deadline for a defenseman who never played for the Leafs and two picks who never played for the Leafs either.

6. Pat Stapleton – (63) PS

Leafs get: a roster spot

Black Hawks get: Pat Stapleton – 63 PS (41G, 286A for 327P, +201 in 545 GP)

This is another one where we’re cheating a little bit: The exact same day the Leafs allowed Gerry Cheevers to be claimed by the Bruins, they also left unprotected a soon-to-be 25-year-old defenseman after trading for him the day before.

Stapleton was a Hawks prospect who was claimed by the Bruins in the intraleague draft back in 1961. He couldn’t stick with the team, only playing 90 regular season games, both of those in his first two seasons under Bruins control.

The Leafs traded Ron Stewart for Stapleton and two other prospects on June 8th, 1965 but left Stapleton unprotected for the draft on the 9th, and the Black Hawks reclaimed him.

With the Black Hawks, Stapleton would make three 2nd All Star Teams (Top 5 in Norris voting all three seasons), make 4 All Star Games, finish Top 5 in Assists in 1968-69 and lead the NHL in Defensive Point Shares in 1966-67. When the Hawks went to the Stanley Cup Finals in 1973, Stapleton led the playoffs in assists. And in the other Final he went to with the Hawks, he finished 3rd in team scoring.

Stapleton left the Black Hawks for the WHA in 1973, winning the WHA equivalent of the Norris Trophy in his first season.

5??? Bathgate and MCkenney for five players – (64.4) PS

Leafs get:

  • Andy Bathgate – 6 PS (19G, 44A for 63P, +11 in 70 GP)
  • Don McKenney – 3 PS (15G, 19A for 34P, +22 in 67 GP)

Rangers get:

  • Arnie Brown – 33.7 PS (33G, 98A for 131P, -11 in 460 GP)
  • Bill Collins – (1) PS (4G, 4A for 8P, -19 in 50 GP)
  • Dick Duff – 1 PS (7G, 13A for 20P, -18 in 43 GP)
  • Bob Nevin – 32.1 PS (168G, 174A for 342P, +20 in 505 GP)
  • Rod Seiling – 7.6 PS (10G, 34A for 44P, -43 in 134 GP)

So this ought to be a controversial choice. But it makes sense, it exposes the flaws in our rankings.

On February 22, 1964 the Leafs traded five players for perennial Hart Trophy-nominee Andy Bathgate and Don McKenney.

Bathgate was one of the best players in Rangers history, winning the Hart in 1958-59 – though he shouldn’t have won – and finishing Top 5 in voting in ’57, ’58 and, most recently, in ’62. Bathgate had also made multiple end of year All Star teams, most recently making the the 2nd Team the previous season.

There was only one problem: Bathgate was born in 1932.

Don Mckenney had long been the franchise player of the Bruins, who were bad, until getting traded to the Rangers the season before. He was born two years before Bathgate.

Arnie Brown was a defensive prospect who had could not make the Leafs so far.

Bill Collins was a prospect forward yet to play an NHL game.

Dick Duff was a Top 6 forward with the Leafs since the mid ’50s. He was younger than both Bathgate and McKenney.

Bob Nevin was a youngish middle 6 forward who had finished 2nd in Calder voting in his first full season in the league. (He had never scored as many points since.)

Rod Seiling was an even younger defensive prospect than Brown, who had played even fewer games with the Leafs.

Bathgate played only a season and a quarter for the Leafs, but the Leafs won the Cup in 1964. For Leafs fans now, acquired a star forward to bring the Leafs a Cup would be worth any future sacrifice. I know that’s how I would feel.

Our method ignores the playoffs, so it ignores the fact that Bathgate helped the Leafs win a Cup. And that is dumb. The Worst Leafs Trade of All Time cannot have led to a Cup.

On the other hand, here are Bathgate’s playoff stats in 1964:

  • Tied for 2nd in Goals (with two others)
  • 6th in Assists
  • Tied for 5th in Points
  • A team-worst -4.

Is it possible that another forward could have delivered this? We’ll never know.

Bathgate was no longer a star. His next season for the Leafs was his worst season since he was 22 and he would never again recover his form. The Leafs figured this out pretty quickly and he was traded at the end of that season to Detroit. (He also missed 15 games, which was another indication.)

McKenney also contributed to the Cup:

  • Tied for 5th in Goals (with two others)
  • Tied for 3rd in Assists
  • 4th in Points
  • 5th in Plus/Minus.

McKenney had a better playoff than Bathgate. (At least without knowing Ice Time.)

But, like Bathgate, his next season was his worst in years; in McKenney’s case it was the worst of his career. So the Leafs waived him.

Arnie Brown got off to a very rough start in New York but eventually turned into a dependable depth defenseman for the Rangers. He was traded to the Red Wings in 1971.

Collins would not make the Rangers and he was waived in 1967 but he made the NHL because the North Stars picked him up.

Dick Duff finished off the season well but then had the worst season of his a career and was traded to the Habs before the calendar year was out, where he would win 4 Cups and somehow make the Hall of Fame.

Bob Nevin became a Top 6 forward for the Rangers, he has the 3rd most points for them between this trade and when he was traded to Minnesota in 1971.

Seiling finished Top 5 in Calder voting the next season. He then became a fixture of the Rangers blue line for the next decade, helping lead them to a the Cup final in 1972. But the reason this trade is only 5th is because, before all that, Seiling was left unprotected in the expansion draft because he got off to a bad start on the Rangers – the Blues grabbed him and the Rangers had to trade some players to get him back.

Factoring in the Cup – one of many the Leafs won in the ’60s – this one doesn’t deserve to be so high, but the Leafs gave up a lot for not many games from two aging stars.

4. A Pick for the Rights to Parent – (67.1) PS

Leafs get:

  • 1973 First Round Pick (Bob Neely) – 9.6 PS (36G, 53A for 89P, -65 in 261 GP)
  • Future Considerations:
    • Willie Brossart – 0.8 PS (0G, 1A for 1P, +2 in 21 GP)
    • Doug Favell – 9.8 PS (26-26-16, .888 SV%, 3.54 GAA, 1 SO)

Flyers get:

  • Bernie Parent – 73.3 PS (177-60-55, .914 SV%, 2.24 GAA, 40 SO
  • 1973 Second Round Pick (Larry Goodenough) – 14 PS (15G, 56A for 71P, +72 in 129 GP)

On May 15, 1973 the Leafs traded Bernie Parents’ NHL rights to the Flyers along with a pick.

The Leafs had acquired Parent in a pretty good trade. However the Leafs would not make Parent their #1 and he left for the WHA. There he played for the Philadelphia Blazers, where he was shelled. When he returned to the NHL the Leafs moved him to Philly for picks.

The Leafs’ drafted Bob Neely 10th overall in 1973. If you can consider a 10th overall pick a bust, Neely is probably a bust. The Leafs traded him to Colorado in 1978 for cash. The Rockies liked him so much they traded him back to the Leafs for cash four months later.

To sweeten the deal Philly through in Dough Favell, Philly’s starter before they acquired Parent. Favell was a backup for three years in Toronto before he was also traded to Colorado.

Finally, some sources include Willie Brossart as part of the “future considerations”. Brossart was a AAAA defenseman for the Flyers. The Leafs traded Brossart to Washington in November 1974.

Parent led the Flyers to two Stanley Cups and one other SC Final. He won the Conn Smythe both times they won the Cup. Parent also won two Vezinas and his 1973-74 season is one of the best ever by an NHL goalie – by Goals Saved Above Average (GSAA) it is the best regular season by a goalie.

Parent retired as a Flyer after a career-ending injury in 1979.

3. 2011 Pick Swap – (86.6)* PS

Leafs get: 2011 First Round Pick – 0 PS

Ducks get:

  • 2011 First Round Pick (Rickard Rakell) – 32.2* PS (129G, 154A for 283P, -2 in 447 GP)
  • 2011 Second Round Pick (John Gibson) – 54.4* PS (139-103-33, .918 SV%, 2.53 GAA, 19 SO)

At the 2011 NHL draft the Leafs traded the 1st round pick they received in the Tomas Kaberle trade (i.e. Boston’s) plus their 2nd round pick to move up to the 22nd spot in the first round. The Leafs were picking at 25 but apparently were concerned they would not get the player they wanted there, so they moved two picks for one.

The risk with this type of move is that there is a world in which the two players picked with the picks traded away add up to being better than the one player picked for your team. And that’s what happened here, to an extreme degree.

The Leafs took Tyler Biggs. Biggs never made the Leafs and was eventually included as part of the 2nd Phil Kessel trade (see above).

The Ducks took Rakell with the last pick in the first round. By Point Shares Rakell is only the 15th best player in the 2011 draft but that is both considerably better than Tyler Biggs and also way better than his draft position. Rakell is 3rd on points on the Ducks since he entered the league in 2012.

The 3rd best player in the 2011 draft by Point Shares is John Gibson, whom the Ducks drafted with the Leafs’ 2nd Round pick. Gibson has been the Ducks’ starter since 2015.

2. Raycroft for Rask – (92.6)* PS

Leafs get: Andrew Raycroft – 10.6 PS (39-34-14, .890 SV%, 3.17 GAA, 3 SO)

Bruins Tuukka Rask – 103.2* PS (291-158-64, .922 SV%, 2.26 GAA, 50 SO)

This one has been litigated a lot: at the 2006 NHL draft the Leafs traded one of their top 2 goalie prospects – Rask was drafted in 2005 – for former Calder Trophy winner Andrew Raycroft. Nobody knows why.

Yes, the Leafs needed a starting goaltender. Belfour was 40 and they were letting him walk after a bad season.

But Andrew Raycroft’s 2005-06 season was worse than Belfour’s:

  • Belfour: 22-22-4, .892 SV%, 3.29 GAA, 0 SO -13 Goals Saved Above Average (GSAA)
  • Raycroft: 8-19-2, .879 SV%, 3.72 GAA, 0 SO, -19 GSAA

Raycroft won the Calder before the lockout, so two seasons earlier than the trade. And he won the Calder, not the Vezina. (Though he did finish Top 5 in Vezina voting that season.)

Rask was the 21st pick in the 2005 draft. Infamously the Leafs decided Justin Pogge (career (0.2) Point Shares) was the goalie to bank on, not Rask. But what nobody understands is why Raycroft was worth Rask, or why Rask wasn’t worth Raycroft plus more assets.

Raycroft’s two seasons in Toronto were not good. The Leafs let him walk at the end of his contract.

Rask won the Vezina in 2013-14 and finished Top 5 in voting another season. He led the NHL in Save Percentage and GAA in 2009-10 and he’s led the NHL in shutouts twice. In 2012-13 he led the Bruins to the Stanley Cup Final, leading the playoffs in Shots Against, Saves, Save Percentage and Shutouts. He has led the playoffs in Shutouts two other times as well.

1. Tom Kurvers for a Pick – (93) PS

Leafs get: Tom Kurvers – 5.4 PS (15G, 40A for 55P, -20 in 89 GP)

Devils get: 1991 First Round Pick (Scott Niedermayer) – 98.4 PS (112G, 364A for 476P, +172 in 892 GP)

If the Larry Murphy trade is the most infamous Leafs trade of the last 25 years – and the Rask trade is way up there too – the most infamous trade of the last 30 years is the Tom Kurvers trade.

Many Leafs fans view the deal which sent the Leafs’ 1991 First Rounder to New Jersey for Tom Kurvers on October 16, 1989 as the Worst Leafs Trade of All Time. At least by regular season Point Shares, they are right.

Tom Kurvers was a journeyman defenceman in his age-27 season. He had played 138 games for the Habs, where he was a plus, but then played 55 games for Buffalo where he was a -13 while scoring 23 Points, and then he was a serviceable player for a mediocre to bad Devils team for 131 games.

Here are two likely reasons the trade happened:

  • Kurvers put up 15 points in 19 games in the Devils’ unlikely run to the Eastern Conference Finals in 1988
  • the pick was nearly two seasons away and, in theory, there was no way for the Leafs to know just how bad the 1990-91 Leafs would be.

Of course, the reason you don’t trade your 1st round picks if you are not sure if you’re going to be good is because they are worth more if you’re bad.

Kurvers played just over a season’s worth of games for the Leafs before he was traded to Vancouver for Brian Bradley. (See #27 to see how that worked out.)

We all know what happened with the draft pick, it went to the Hall of Fame:

  • 3 Stanley Cups
  • Two other SC Finals appearances
  • 1 Norris and one 1st Team All Star, plus another Top 5 Norris voting finish
  • He led the playoffs in scoring 2003
  • And averaged 25:30 minutes during the regular season (since 1998-99) and about the same in the playoffs.

And that’s just what he did before he went to Anaheim.

This one hurts. And, by our method, it’s the worst trade the Leafs ever made.


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.)

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