When I moved to Toronto from Chicago in 2002, I left a city which hadn't won a Stanley Cup since 1961 for one that hadn't won a Cup since 1967. I'm also a Cubs' fan, so the adjustment to a city with a championship drought was an easy one.
However, the Blackhawks of course won the Stanley Cup three times in the past six years while, in the same time, the Leafs have won a total of three playoff games. The Blackhawks went from being rated the worst franchise in all of sports by ESPN to being the class of the NHL, on and off the ice. The path they took involved being very bad, drafting very high and very well for a couple of years, developing their own players, signing a few key free agents, making a few shrewd trades, and all while managing to stay within the confines of the salary cap.
The Toronto Maple Leafs meanwhile have been mediocre for the past decade or longer, and currently are in their 49th straight Cupless season, the same number of years the Blackhawks went before their 2010 championship. The Leafs are doing some things right, but they just might, might, might be getting themselves in position for a resurgence.
What has doomed them over and over in the years I have watched them is an incredible impatience by management and the fans. They always want the shiny metal object they see, and often pay dearly for it. For example, some of their recent big free agent signings have included David Clarkson, David Booth, and Jeff Finger.
On the trade front, the Leafs have traded away some pretty decent players and some draft picks that turned out to be gold mines for the acquiring teams. Going back to 2007, the Leafs traded prospect Tuuka Rask for Andrew Raycroft (who the Bruins were going to cut anyhow). The Leafs have not had a steady goalie since, while Rask has become an elite goalie (though Blackhawks fan remember him best for 17 seconds in 2013 and the Cup winning goal by Dave Bolland).
After the Blackhawks won that 2013 Stanley Cup, the Leafs looked to take advantage of the Hawks' desperate salary cap situation by trading for Toronto native Bolland. Well, Bolland played just 23 games with the Leafs due to injury, and then signed with Florida as a free agent. Bolland's game fit in perfectly with the Hawks as a depth center, but in Toronto, where everyone expects a savior to appear, Bolland was not suited to a bigger role.
Back in 2009, the Blackhawks traded their 2nd round pick in the draft for Toronto's 2nd and 3rd the following year. The Leafs packaged that pick to get Phil Kessel from Boston, while the Blackhawks used one of their picks to grab Brandon Saad. Advantage: Blackhawks.
And to get Kessel the Leafs gave up an unprotected first round pick that turned out to be Tyler Seguin, as well as a pick that Boston used to select Dougie Hamilton. The front office never thought the Leafs would have such a high pick and so they didn't protect it in the trade.
The Blackhawks front office has not been perfect (exhibit A: Trevor Daley) but it has been pretty close. Among the smartest moves the Hawks ever made was bringing in Joel Quenneville, who just signed an extension through 2020. He has been the perfect coach for the team.
Meanwhile, the Toronto media recently started campaigning for Mike Babcock to win the Jack Adams (Coach of the Year) Award. The season wasn't even half way completed but because the Leafs were doing fairly well since early November, this somehow meant Babcock is already the coach of the year. That loss of focus is what has damned Toronto in recent years. Meanwhile, Chicago has focused on "One Goal" and achieved it three times. Incidentally, since that Jack Adams talk started the Leafs have lost three straight, including a disastrous 7-0 blowout loss to San Jose and a loss to the struggling Blue Jackets.
But there is some hope for Toronto. Prospects William Nylander and Mitch Marner look like they are going to be legitimate NHL players soon, and they could very well be the start of a core that the Leafs have been desperately lacking.
The Leafs biggest problem is believing that Joffrey Lupul, Tyler Bozak, James van Riemsdyk, Dion Phaneuf, Morgan Rielly, Nazem Kadri, and Jake Gardiner are a "core" in the same way the Blackhawks have a core.
Well, those current Leafs players are nowhere near the talent levels of Jonathan Toews, Patrick Kane, Duncan Keith, Brent Seabrook, Corey Crawford, Niklas Hjalmarsson, and Marian Hossa. And the Blackhawks front office has consistently augmented the roster thanks to great scouting, drafting, trades and free agents, which is how the Blackhawks were able to win the Cup in 2015 and still look like a genuine contender in 2016 despite salary cap limits.
The Leafs have tremendous resources and have bolstered their front office by adding Stanley Cup veterans Brandon Shanhan as team president, Lou Lamoriello as GM, and Babcock as head coach. They seem to be on the right track. But for now, and probably for a few more years, the biggest difference between these two hockey towns is that one city plans championship parades, and the other one actually holds them.
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