Puck Daddy's Most Disappointing Summer Series: Toronto Maple Leafs Edition

(Ed. Note: There’s entirely too much sunshine in the summer. So your friends at Puck Daddy are offering a month of thrown shade and perpetual gloom. Behold, our Summer of Disappointment series, in which we ask fans of all 30 teams to recall the biggest bummer moments, teams and players in franchise history! Please wade into their misery like a freezing resort pool, and add your own choices in the comments!)

Written by Pension Plan Puppets

Most Disappointing Team: 2009-2010 Maple Leafs

Look, obviously I have a litany of seasons to choose from - a pedant might note that there's at least 47 recent ones - so most people will not agree but I'll never forget getting a message from @GoddTill in January of 2010 during a 5-3 loss to the Kings: "I can't believe we got worse".

The Leafs had hired the biggest name GM available in Brian Burke and despite warnings from old wise heads, there was a lot of optimism going into his tenure. This was the point when fans' trepidations about the Truculence Era started to loom large. The Leafs would of course go on to finish 2nd last and give up some kid named Tyler Seguin. At least they didn't trade him away for nothing.

Most Disappointing Maple Leaf: Wilf Paiement

The 2nd overall pick in 1974 made his way to Toronto in exchange for fan favourite Lanny MacDonald. Legend has it that Harold Ballard got him to wear 99 so Leafs fans would think they also had a young exciting player and might forget that there was no good reason to trade Lanny. I'm going to believe that so that I can give a sop to the older fans.

Most Disappointing Moment in Maple Leaf History: Game 7 1993

Gretzky getting away with murder because of Kerry Fraser's callowness has been debated to death and every so often a particularly cheeky opposition fan will say "sure, but they still lost game seven" just prior to having their life ended with extreme prejudice. Well, they aren't wrong.

The Toronto Maple Leafs were playing their 21st game in 42 nights in the kind of playoff run that galvanized an entire country and who was waiting on the other side? The Auld Enemy, the Montreal Canadiens. They were at home in front of what will confuse fans that have watched Leafs games for the last decade: a rabid crowd that could tilt the ice for the home team. I know, it's hard to believe. This was it, the Leafs were going to win and then beat the Habs for the Cup and then we could end hockey because it would never have gotten any better.

Instead, Bob McKenzie said Gretzky looked like he was playing with a piano on his back and the Great One potted a hat trick to dash millions of dreams. The worst part was that the goal that made it 5-3 was such a stupid bounce and the Leafs dicked around with the puck for a minute with the net empty before strolling up ice and making it 5-4 but it was too little too late. The Leafs have never been that close to the final since.

Most Disappointing Maple Leafs Transaction: Captains Leaving

The list of disappointing things about the Toronto Maple Leafs is long and distinguished but one aspect that really stands out is how terribly things tend to end with their captains. If one were to look to a pattern, they might notice that this list starts after the last Stanley Cup and continues to this day. If I had more space I might tie these captains' departures to larger themes about how the Leafs often act like a Mickey Mouse operation.

Dave Keon was forced out of the NHL by Harold "May He Rot In Hell" Ballard, Darryl Sittler was traded to Philadelphia for almost literal garbage, Rick Vaive was traded to Chicago along with Steve Thomas in part for one of my favourite Leafs from my childhood Ed Olczyk (yeah, makes no sense now but I was 5!), Rob Ramage was claimed in an expansion draft (this may be how Clarkson is dealt with!), Doug Gilmour was actually was prescient about MLSE and demanded a trade but don't worry because we don't talk about it, and Mats Sundin was driven insane by losing and wouldn't accept a trade so instead he lounged around for a few months and signed in Vancouver instead of retiring as a Leaf.

The good news is that Phaneuf's contract probably means that he will retire as a Leaf and then we can see if maybe it's the Captain's Curse that is killing the Leafs.

Most Disappointing Maple Leafs Coach/Executive: Brian Burke

The running theme of this story is that the Leafs just disappoint their fans in sometimes creative, sometimes mundane, but always numerous ways. This is a tough choice because the Leafs have had some real bums behind the bench or in the press box. Let's put it this way, the blog's existed for 8 years and so far we're 4-for-4 in being demonstrably smarter than the GM's that have run the team.

Plenty of GMs in Toronto have been bad and of course Harold Ballard probably could count but the majority of them can't be counted as disappointments because who the hell would have had positive expectations for them?

However, one man came swaggering into Toronto with bold proclamations on the gravity of the job and outlined a clear path (and timeline!) to success all the while flashing a big, bright Stanley Cup ring to allay any fears. Just over four years later, he departed leaving behind a string of awful UFA signings, a dinosaur as coach, a prospect system routinely ranked in the bottom third of the league, and a front office of buffoons. Although he did snap at Steve Simmons and the Sun a lot so it wasn't all bad.

Most Disappointing Maple Leafs Fashion Choice: Pyjama Jerseys

The Toronto Maple Leafs have the kind of uniform that is almost impossible to screw up. And yet, when the NHL came back from their lockout (uhhh 2004-05 Edition) Reebok managed to screw it up monumentally and in the most mundane fashion possible.

It wasn't like they changed the logo or used superfluous piping as they did with some other hideous jerseys (or "sweaters" for the old-timers). No, they just didn't add any stripes on the waist so the jerseys look like something the team would wear at practice.

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Other disappointments (in order of appearance): New York Rangers • Calgary Flames • St. Louis Blues • New York Islanders • Dallas Stars • Boston Bruins • Colorado Avalanche • Washington Capitals • Ottawa Senators • Arizona Coyotes • Minnesota Wild • Edmonton Oilers • San Jose Sharks • Winnipeg Jets • New Jersey Devils • Los Angeles Kings • Florida Panthers • Carolina Hurricanes • Buffalo Sabres • Montreal Canadiens • Tampa Bay Lightning • Chicago Blackhawks • Columbus Blue Jackets • Nashville Predators • Detroit Red Wings • Anaheim Ducks • Philadelphia Flyers • Pittsburgh Penguins • Vancouver Canucks