The Toronto Maple Leafs are the second most successful and historic team in the NHL. On one hand, their 13 Stanley Cup championships are only outmatched by the Montreal Canadiens (24). But as everyone knows, they've been one of North America's worst teams in the 21st century. Toronto hasn't won a Cup in the post-Original Six era. In fact, they haven't reached the Finals since last winning it all in 1967. There are many reasons why. It could be porous drafting, bad reffing (see Wayne Gretzky's high stick on Doug Gilmour), bad free agent signings or even terrible coaching.
But the Maple Leafs have done one thing worse than basically every other NHL team: Trading. As you'll see on this list, they made a number of trades that seemed smart at the time, but would only come back to haunt them for long periods of time.
Here are 15 bold offseason moves the Maple Leafs made that flopped big time.
18 Giving Away Phil Kessel to Pittsburgh
It only made sense for the Maple Leafs to trade away Phil Kessel in the 2015 offseason, considering that they were about to start a rebuild and had no reason to keep his $8 million cap hit around for seven more years. So they packaged him in a deal with the Pittsburgh Penguins which brought Nick Spaling, two draft picks and prospects Scott Harrington and Kasperi Kapanen.
Now, the Kessel trade helped them become so bad that they won the draft lottery in 2016 and got to choose Auston Matthews. But still, Kessel led the Pittsburgh Penguins to consecutive Stanley Cup championships. Toronto got virtually nothing for a franchise superstar, and they've had to watch an old friend succeed big time without them. Toronto got totally robbed in this deal but Matthews is at least a nice consolation prize from the one-sided trade.
15 Trading For Dion Phaneuf
File this under "The worst trades of all time that never made sense for either side and didn't benefit anybody". Dion Phaneuf was one of the top blueliners in the NHL during his tenure with the Calgary Flames. He scored 20 goals in his rookie year, followed by consecutive 17-goal seasons. Phaneuf was a force on defence for the Flames, but they chose to ship him to the Toronto Maple Leafs in a blockbuster for the ages.
Phaneuf, Keith Aulie and Fredrik Sjostrom were sent to Toronto in exchange for tough guy Jamal Mayers, defenceman Ian White and forwards Matt Stajan and Niklas Hagman, who were all solid fits in Toronto. Phaneuf was solid but not really that much of an impact player. Toronto made him captain and gave Phaneuf a seven-year extension worth $49 million. They somehow got the Ottawa Senators to take on his contract at the 2016 trade deadline. But man, this trade was nothing but frustration for Toronto.
14 Sending Tomas Kaberle To Beantown
Kaberle was one of the top offensive blueliners in the NHL during his time with the Maple Leafs. But he was aging, in a contract year and had no long-term future on a young Maple Leafs team. One of the top trade candidates at the 2011 deadline, Toronto sent Kaberle to the Boston Bruins in exchange for Joe Colborne and a first and second round draft pick.
Colborne was among the top prospects at the time, but played just 16 games for the Leafs before being traded to the Calgary Flames. Toronto wasn't able to use the draft picks to their advantages, either, as they wasted them on players who never panned out. Though he didn't make much of an impact in Boston, Kaberle did win a Stanley Cup with them. He got the last laugh as the Leafs made a terrible move in giving away a top blueliner to a division rival, while receiving no impact pieces in return.
13 Trading For Vesa Toskala
Toskala had won 23 and 26 games for the San Jose Sharks in 2006 and 2007, respectively. Despite showing plenty of flashes in goal, Toskala couldn't take the starting job away from long-time Sharks goalie, Evgeni Nabokov. San Jose decided to clear the goalie controversy by sending Toskala and forward Mark Bell to Toronto in exchange for a 2007 first round pick, two second rounders and a fourth round pick.
Toskala went just 62-54-20 during his time with Toronto, with a brutal .894 save percentage and 3.08 goals against average. Toskala spent less than three years in Toronto before being traded to the Calgary Flames. San Jose used their 2007 first rounder on Lars Eller, but had the Leafs kept it, they could have used it on Kevin Shattenkirk, Max Pacioretty or P.K. Subban. Just some food for thought.
12 Sending Alexander Steen to St. Louis
Steen had some good years early on in Toronto. During his 2005-06 rookie season, the flashy play-maker scored 18 goals and 45 points. He'd follow it up with consecutive 15-goal seasons, which were pretty decent numbers for a second/third liner. But during the 2008-09 season, Toronto sent Steen and stay-at-home defenceman Carlo Colaiacovo to the St. Louis Blues in exchange for sniper Lee Stempniak.
Steen has since become a reliable second liner for the Blues. He's good for 50-60 points a year when healthy, and has hit the 20-goal mark four times with them. Steen has helped the Blues become a juggernaut in the Western Conference, while the Leafs never got anything good out of Stempniak. Just another example of Toronto giving up on a talented young player for no good reason.
10 Trading Lanny McDonald To the Rockies
Not only does he have the greatest moustache in NHL history, but McDonald is one of the greatest captains and all-around players to ever live. He scored 500 goals and 1,006 points, and led the Calgary Flames to the Stanley Cup championship in 1989. He was a superstar for the Maple Leafs during the '70s, putting up 80-plus points a season. Maple Leafs GM Punch Imlach didn't get along with Leafs star Darryl Sittler, and looked for a trade. When it didn't work out, Imlach got back at Sittler by trading away his close friend (McDonald), to the Colorado Rockies in 1979 for Wilf Paiement, Pat Hickey and Joel Quenneville.
Quenneville spent just two seasons with Toronto, while Paiement and Hickey each registered 20-goal seasons. But those two players only played three seasons each with the Leafs before moving on. McDonald was a superstar and leader all the way up until his retirement. A bad move on the Leafs part, indeed.
9 Getting Tyler Biggs for John Gibson and Rickard Rackell
After giving up his first round pick in 2011 (we'll get on this later), in the trade for Phil Kessel, Leafs GM Brian Burke was desperate to get the team some first rounders. Burke longed for American sniper Tyler Biggs, so he traded up to get the kid with the 22nd selection. In exchange, he gave up his 2011 first and second rounders to the Anaheim Ducks.
Biggs never appeared in an NHL game, while Rackell (who was selected 30th overall), scored 33 goals for Anaheim, leading them to the Western Conference Final in 2017. He also scored 20 goals in 2016. But Rackell was only half of the return. Anaheim also drafted goaltender John Gibson with the second round pick. He's become one of the NHL's top goalies, taking the Ducks to the Pacific Division crown in his first three seasons.
8 Trading Frank Mahovlich To Detroit
Mahovlich was one of the NHL's top goal-scorers through the '60s and '70s. He led the Toronto Maple Leafs to Stanley Cup championships in 1962, '63, '64 and '67. The perennial All-Star scored 597 points during his time in a Leafs uniform, placing him seventh in franchise scoring. But in 1968, the Maple Leafs opted to package Mahovlich to the Detroit Red Wings in exchange for Paul Henderson, Floyd Smith, Doug Barrie and Norm Ullman. Toronto appeared to believe that Mahovlich was past his playing prime, but he'd have five more 30-goal seasons in him.
Toronto hasn't won a championship since the Mahovlich trade. They had no reason to give up on their franchise superstar, as Mahovlich remained one of the league's best players for a few more years. Henderson and Ullman had some impact, but not quite what Mahovlich did in Toronto.
7 Sending Anton Stralman to Calgary
The Maple Leafs drafted Swedish defenceman Anton Stralman with the 216th selection in the 2005 NHL Draft. Though he didn't quite make an impact in his first two NHL seasons, Stralman was fairly young and displayed some strong puck-moving skills. But that wasn't enough for the Leafs. During the summer of 2009, Stralman was packaged in a deal and sent to the Calgary Flames for bottom-six forward Wayne Primeau and a second round pick. Stralman bounced around from team-to-team but has since found a niche with the Tampa Bay Lightning, where he's become a very reliable top-four defenceman. He helped them reach the Stanley Cup Final in 2015 as well.
Primeau scored just three goals for the Maple Leafs in his one season there before retiring. Toronto was rebuilding and had no reason to give up on a young defenceman in Stralman. They won't be forgetting this bad deal any time soon.
6 Doug Gilmour Heads to New Jersey
There's no easy way to describe just how great Doug Gilmour was. Anywhere he went, he became a respected leader and was a superstar. He was a fan favorite wherever he played, and that especially included the Toronto Maple Leafs. The 2011 Hockey Hall of Fame inductee scored 450 goals and 1,414 points in his career, while helping the Calgary Flames win the Stanley Cup in 1989.
After a frustrating '80s decade, the Leafs acquired Gilmour in 1992, and he'd bring back prominence to the franchise. Gilmour posted a pair of 100-point seasons and took Toronto to the conference finals in both 1993 and 1994. As the Leafs began to struggle in the late '90s, Gilmour was sent to the New Jersey Devils that brought over Steve Sullivan, Alyn McCauley and Jason Smith -- none of which panned out. It was tough for Leafs fans to accept a Gilmour trade, and it was even worse when Toronto got virtually nothing out of it.
5 Acquiring Phil Kessel From Boston
Former Leafs GM Brian Burke was all about making the big move. Despite the Leafs having missed the playoffs in four straight years, Burke decided that it was worth surrendering the team's first round picks in 2010 and 2011 to acquire Phil Kessel from the Boston Bruins. Kessel was coming off a 36-goal season with Boston, but couldn't come to terms on a new contract with them, causing the trade to happen. Kessel was far from a bust in Toronto. He scored at least 20 goals every season, including four 30-goal seasons. The only problem was other than Kessel, the Leafs were downright awful and only made the playoffs once in his tenure.
Boston used the second overall pick in 2010 on Tyler Seguin, who's consistently among the top scorers every year. In 2011, they used the first round pick via Toronto on skilled defenceman Dougie Hamilton. The ironic part is Kessel, Seguin and Hamilton have all switched teams since. The Leafs can thank Boston for being silly enough to trade those two stars away, but it doesn't mean Toronto will live down the Kessel trade any time soon.
4 Trading Darryl Sittler to the Flyers
Sittler will go down as one of the greatest Toronto Leafs to ever live, though many of you may only remember him as the guy who scored 10 points in a single game (an NHL record, by the way). Sittler was one of the NHL's top scorers during the '70s, posting consistent 30-40 goal and 80-100 point seasons. There were few players who could take over a game like him.
But Sittler had a rough relationship with the front office, most notably GM Punch Imlach. After years of trying to get Sittler to accept a trade, he was finally sent to the Flyers in 1982 for Ken Strong, Rich Costello and a second round pick. None of those players left an impact in Toronto, while Sittler had a couple of more strong seasons with the Flyers. The Maple Leafs struggled throughout the '80s after trading Sittler. There was no reason for the team to give up on their franchise star. But hey, there's a reason we made this list!
3 Sending Bernie Parent To Philadelphia
Few NHL goalies had a marvelous career so similar to the one that Philadelphia Flyers icon Bernie Parent had. He won 271 games, a pair of Vezina Trophies and led the Flyers to the Stanley Cup in 1974 and '75. Parent was one of the NHL's most dominant goalies of the '70s, and the Leafs surely could have used him.
The Flyers chose Parent in the 1967 Expansion Draft, only to deal him to the Maple Leafs in 1971. After a frustrating two years with the Leafs, Parent was traded back to Philadelphia in 1973, with Doug Favell and a 1973 first round pick going back to Toronto. Favell spent just three seasons with the Maple Leafs, and Parent would become an icon in Philadelphia. The Hall of Famer is widely regarded as one of the best players to ever live, and it's amazing how the Leafs opted to give him away for so little.
2 Swapping Tuukka Rask For Andrew Raycroft
Raycroft won the Calder Trophy with the Bruins in 2004 after winning 29 games and leading them to the Eastern Conference's second seed. Despite a down year in 2005-06 that saw him play in just 30 games, the Maple Leafs envisioned him as their goalie of the future. So they traded away elite goalie prospect Tuukka Rask to the Bruins for Raycroft. His first season in Toronto went well, as Raycroft won 37 games and nearly guided them back to the playoffs. But Raycroft left Toronto after the 2008-09 season, while Rask went on to become a star.
Though Rask was Tim Thomas' backup during the run to the 2011 Stanley Cup victory, the Finnish star led them to the Final again in 2013, while taking home the Vezina Trophy in 2014. Rask has become one of the NHL's elite goalies, all while the Leafs spent year-after-year looking for a true No. 1.
1 Getting Tom Kurvers, Losing Scott Niedermayer
Tom Kurvers was a solid and reliable top-four defenceman throughout his NHL career, but he was never a superstar by any means. However, the Maple Leafs were desperate for a blueliner and acquired Kurvers during the 1989-90 season. Toronto threw in their 1991 first round pick in the trade, which would wind up being the third overall selection. Kurvers spent just two years with the Leafs, and the Devils wound up using that very pick on world class defenceman Scott Niedermayer. What can we say? He's the biggest winner ever, winning the Memorial Cup, World Junior gold, four Stanley Cups, two Olympic gold medals, the World Cup of Hockey and World Hockey Championship gold.
Had it not been for Nicklas Lidstrom, Niedermayer would have probably won over five Norris Trophies. He completely changed games on his own with slick skating, puck-movement and shutdown ability. He's a top-10 defenceman of all-time, and the Leafs lost out on him by simply trading for a fairly average player. Oh, how that Stanley Cup drought could have ended by now if they just held onto the third selection in 1991.