Toronto Maple Leafs: How Did We Get Here?

A closer look at the Toronto Maple Leafs and how they ended up where they are right now.

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With the NHL Regular Season winding down, we wanted to take a closer look at each of the seven Canadian teams to figure out how they ended up where they are right now.

Because they’re the most talked about bad team in the country, starting with the Toronto Maple Leafs only made sense.

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Toronto’s biggest problem isn’t Phil Kessel and it isn’t Dion Phaneuf.

As much as they’re easy and preferred targets, the former is one of the best pure goal scorers in a league where guys that can put the puck in the back of the net are at a premium and the latter is actually a solid defenseman that brings a little sandpaper to the festivities whenever he’s on the ice.

The trouble for both is that they’re not exactly cut out to be front and center in this market, where criticism is constant, every play is scrutinized and players from generations past are held up as icons you can never compare to even though none of them managed to bring the Stanley Cup back to “The Big Smoke” either.

Obviously, there have been some bloated contracts that didn’t pan out over the last decade – Jason Blake, Mike Komisarek, David Clarkson – but the greatest contributor to Toronto being in a position to miss the playoffs for the ninth time in the last 10 seasons is the fact that the team has completely misfired on the NHL Entry Draft and the majority of the trades they’ve made during that time.

Outside of first-round draft picks, Toronto doesn’t have anyone they’ve drafted in the last seven years on their roster. There are no third-round picks that provide third-line depth, no sixth-round finds that have blossomed into top-six forwards or top-four defensemen; just a series of swings and misses.

You can’t blow the draft that bad for that long and expect to be successful – you become too reliant on spending valuable salary cap dollars to fill roles that should be handled by youngsters on entry-level contracts or picking up spare parts off the scrap heap that have already proven they’re not long-term solutions.

What compounds those issues is that no matter who is pulling the trigger on deals in Toronto – John Ferguson Jr. or Brian Burke or Dave Nonis or whoever – they consistently come out on the wrong side of the results.

They bet on Justin Pogge instead of Tuuka Rask.

They trade a first- and second-round pick for Vesa Toskala and Mark Bell, only to waive Bell a year later and ultimately swap Toskala and free agent flop Jason Blake for Jean-Sebastien Giguere, who leaves as a free agent after one injury-plagued season.

They give Jeff Finger $14M over four years Tim Connolly $9.5M for two seasons when no one else was lining up to pay either of them that kind of money.

It’s only then when you add Kessel bristling under the pressure, Phaneuf being paid like a first-line defensemen when he’s really a solid second unit guy and the massive extensions they received (along with Tyler Bozak) that things start get real bad.

One or two misfires in the draft and a couple bad free agent deals don’t have to be the death of a franchise if there are solid returns in those areas in the surrounding years, but season-after-season of coming up empty is crippling and it’s even worse when you’re playing in the most critical market in the business.

They have a couple solid core pieces to build around going forward – Rielly, James Van Riemsdyck, Jake Gardiner – and last year’s first-round draft pick William Nylander looks like a future All-Star, but it’s going to be a couple years before this team is back in contention.

Provided this new regime doesn’t screw things up like everyone else has.

Tomorrow on How Did We Get Here? features a look at the Edmonton Oilers.

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