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Brendan Shanahan will have to contend with a team with limited cap space and a roster which isn’t good enough to contend.<240>Fred Lum/The Globe and Mail

As far as analogies go, Tim Leiweke's wasn't half bad on Monday.

Moments after introducing Brendan Shanahan as the new head of the Toronto Maple Leafs, the MLSE president was likening the three very different challenges in front of him to three very different ships.

With the Leafs obviously being the most challenging to get a handle on.

"If TFC is the sailboat and ultimately the Raptors are the yacht," Leiweke said, rattling off the names of his improving soccer and basketball teams, "the Leafs are a massive cruiser. And it takes a lot to turn them around, and it takes a lot to shift strategy.

"This is not a task you take lightly. I needed some time to understand what was right and wrong here."

In the interests of helping out the two new guys – Leiweke, who's been on board since last June, and Shanahan, who enters the picture in the wake of an ugly collapse to end the season – here's a basic rundown of why the Leafs cruiser sputtered to the bottom of the ocean starting four weeks ago.

No. 1, the captain shot a couple speed holes into the hull last summer, swapping out decent players for poor ones and spending right to the cap to handcuff the Leafs all year.

More importantly, his first mate – i.e. coach Randy Carlyle – had pointed the fair S.S. Maple Leafs at the nice, cascading waterfall that was their playing style and, despite his protestations over their direction, was never able to change the Leafs course.

So over they went, right as soon as their scorers hit a dip and their goaltenders couldn't bail them out fast enough.

Brendan Shanahan didn't come to his introductory press conference  on Monday prepared with a whole lot of answers and that makes a lot of sense. He hasn't had a lot of time to make judgements, let alone pronounce them in front of hundreds of media and cameras on his first day.

(Leiweke may have been on the hunt for a president of hockey operations for a while, but the serious talks with Shanahan only really materialized in earnest in the past week.)

Shanahan has been playing a much different game the last three years in the NHL's front office, one that's involved appeasing GMs when they made angry calls over suspensions. He made some friends on high, but he made some enemies, too, just as anyone would in the ridiculously difficult disciplinarian job.

Now he takes on an entirely new animal, joining those GMs in a competing front office, and what you had to like about his comments Monday is he isn't afraid to admit what he doesn't know.

Even if what he doesn't know, at this point, is precisely how to fix the Leafs.

"The first thing I'm going to do is head up to the offices and start going through our entire roster, our entire staff and bring myself up to speed," Shanahan said at one point.

What he sees and how the Leafs proceed is of the utmost importance. The franchise can't afford to have as poor an off-season as it did a year ago and can't afford to stumble around in the grey area between contender and bottom feeder without making much progress either way.

The organization needs to decide what they're going to be and who's going to be part of that process. What Monday really signalled more than anything is that Leiweke's putting most of those decisions in Shanahan's hands.

Where he should start is with a thorough evaluation of everyone on staff underneath him, beginning with Carlyle – who was nowhere to be found on Monday in one sign as to how long he'll last – and including everyone up to GM Dave Nonis.

Only then can he turn his eye to the roster, which has obvious issues of its own.

The fact Shanahan comes in with an open mind on things like analytics that the previous administration openly mocked and dismissed is one positive, but there are others, too. He immediately comes across as someone willing to think outside the box, a trait he showed specifically in helping usher in an obstruction-free era with the so-called Shanahan Summit during the 2004-05 lockout.

Shanahan has also already canvassed some of his friends in the game, like Tampa Bay Lightning GM Steve Yzerman, and picked up some words of advice on how to run a team.

"The one thing he's imparted on me is just how hard it is," Shanahan said. "There are 29 other teams, filled with smart people, looking for the best players and that want to win. That's the one thing I took from a guy like Steve, who I've seen go from a player to a manager. It is a very difficult job."

That it is. And what doesn't make it any easier is the fact Shanahan's chosen the biggest, unwieldy ship to start with, one that's been pointed in the wrong direction for years.

At the very least, he can start by throwing a few stowaways overboard.

Follow me on Twitter: @mirtle