When you’ve been playing the game for more than 100 years, there’s not just One That Got Away.
You could fill an entire roster card with Maple Leafs or near-Leafs who reached higher peaks after they slipped through the grasp of Toronto management.
There was the time Wayne Gretzky considered signing with the club closest to home. There was the Canadian Tire CEO courting free agent Steven Stamkos in his prime. There were dealt-away first-round draft picks that morphed into golden tickets (Scott Niedermayer, Tyler Seguin).
And, boy, were there were some trade stinkers. Turns out, John Kordic is no Russ Courtnall. Alexander Steen fashioned himself into a leader, a scorer, and a champion — for St. Louis. Larry Murphy was booed out of town and seemed to enjoy the applause on a couple of Stanley Cup–winning Detroit squads.
Wanna talk fresh pain? The Maple Leafs had the best odds of securing Connor McDavid in the 2015 draft lottery with one ball to go.
But to narrow down our list here, we limited the disappointments to players whose rights were actually secured by the Maple Leafs before they fumbled the elite talent away for minimal (or zero) return.
Here are the five Leafs departures that stung the most. Read ’em and weep.
5. Rick Kehoe, 1974
Accurately identifying a promising talent in the draft, then parting ways with him too early is a trend you’ll see on this list. And it starts with a Kehoe, a 22nd-overall choice in whom Toronto should’ve invested a little patience.
Despite popping off for 33 goals and 75 points in his first full NHL season, the Leafs dealt Kehoe after a sophomore slump to the Pittsburgh Penguins for Blaine Stoughton and a 1977 first-round pick (Trevor Johansen).
Kehoe’s ice time fell off when red-hot rookies Lanny McDonald and Inge Hammarstrom joined the team in 1973-74. He wanted out.
Kehoe tore it up on some god-awful Penguins rosters, and — decades later — another Toronto-to-Pittsburgh sniper, Phil Kessel, would have his wicked shot compared to Kehoe’s. Between 1974-75 and 1982-83, Kehoe averaged 33 goals and 65 points. He never scored fewer than 29 goals or 50 points.
The PIM-dodging right winger peaked with an 88-point, Lady Byng-winning campaign in 1980-81. He was still tickling point-per-game production until a neck injury got the best of him. Kehoe was forced into early retirement in 1984 but had more than enough time to swell Leafs Nation with regret.
4. Steve Sullivan, 1999
God bless Pat Quinn, but the legendary coach and exec probably would’ve liked a mulligan on this one.
In an effort to obtain and clear roster space for high-scoring veteran forward Dmitri Khristich, Quinn placed a 25-year-old Sullivan on waivers at the outset of the 1999-00 campaign.
Unbeknownst to the world, Khristich — a 70-point man twice over — had just about hit a wall and experienced a dramatic plummet in production, mustering a measly 39 points for Toronto over a season and a half before getting shipped to Washington (for just a third-rounder) and, not long after, Magnitogorsk.
The smallish Sullivan didn’t fit Quinn’s preference for edgy vets, so Chicago swooped in and made out like bandits. Sullivan only enjoyed seven consecutive seasons in which he fired 22-plus goals and amassed 60-plus points. Had he remained in T.O., those numbers would’ve put him among the team’s top five leaders for seven straight years (of bad luck).
Sullivan raised his stock with the Blackhawks so high, they were able to flip him to Nashville for two second-round picks at the 2004 trade deadline. Sullivan would deliver the Preds two-and-half seasons of hockey averaging better than a point per game, until finally injuries and age caught up with him. The Ontario boy retired with 747 points as a member of the 1,000-game club.
3. Randy Carlyle, 1978
The player, not the coach.
Toronto drafted Carlyle in the second round in 1976 and gave up on the young blueliner way too soon. In search for a dependable D-man, GM Jim Gregory dealt Carlyle and George Ferguson to the Pittsburgh Penguins for Dave Burrows.
Burrows provided something considerably less than a spark, recording 32 points and minus-14 rating in 151 games with Toronto.
Not only did Ferguson explode into his prime, responding with four straight 20-goal seasons in Pittsburgh, but Carlyle’s early departure stung worse.
Over 397 games as a Penguin, Carlyle put up 323 points from the back end and rapidly grew into one of the most dynamic blueliners of his era. He won the Norris Trophy in 1980-81 before continuing his excellent, 1,055-game career in Winnipeg. He served as captain for both the Penguins and Jets.
Good one, Randy.
2. Tuukka Rask, 2005
There are lopsided trades and then there is the Rask debacle, a regrettable move that seems to sting a little fiercer with each passing spring.
It was Rask standing between the Boston Bruins’ pipes when it was 4-1 Leafs in Game 7 of that 2013 playoff series. It was Rask outduelling Frederik Andersen in seven in 2018 and 2019. And it will likely be Rask — a Cup champion and three-time finalist, still in Vezina form — standing in front of the 2020 Maple Leafs if hockey is to resume and Toronto is somehow able to defeat the Lightning.
Funny thing is, Toronto appeared to grasp Rask’s potential back in 2005. John Ferguson, Jr. drafted the Finn 21st overall, but the Leafs GM made the atrocious mistake of pegging prospect Justin Pogge as his goaltender of the future, deeming Rask expendable before he played a single NHL game.
JFJ dealt Rask to his rival in exchange for 2004 Calder Memorial Trophy winner Andrew Raycroft, who now analyzes Rask’s handiwork as a studio analyst for the Bruins’ local NESN broadcasts. Raycroft posted save percentages of .894 and .876 in his two seasons for the Leafs. Poor Pogge won just once and allowed 27 goals in seven NHL appearances. Now 33, he’s doing well for the Berlin Polar Bears. Seriously.
The best thing about the Rask trade is that no Leafs have to sit behind him on the team bus.
1. Bernie Parent, 1973
Giving up early on a future Hall of Famer and a man who would roundly be regarded as one of the best to ever don a mask is never a good look.
Toronto acquired Parent from offence-chasing Philadelphia in a 1971 deal. The young goaltender studied under his boyhood hero, Jacques Plante, becoming a more technically proficient keeper. He appeared ready to take the mantle, but when the management failed to come to a contract agreement with Parent, he signed a contract with the Miami Screaming Eagles and became the first NHLer willing to jump to the emerging World Hockey Association.
The Eagles never got off the ground, so Parent signed with the WHA’s Philadelphia Blazers and got shelled in his one season spent in the defensively weak league. Felt outcast, Parent wanted back into the world’s best league — just not with the Leafs. His request to stay in Philly and join the Flyers was granted.
Toronto dealt Parent’s rights and second-round pick (Larry Goodenough) to the Flyers for a first-rounder (Bob Neely) and future considerations (Doug Favell) in ’73.
All Parent did in his first two seasons in Philadelphia was win two Vezina trophies, two Conn Smythe trophies, and two Stanley Cups.
Parent’s No. 1 hangs in the rafters and he was named one of the 100 greatest players in NHL history.