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Toronto Maple Leafs president Brendan ShanahanThe Canadian Press

By all accounts, Casey Bailey should be a Buffalo Sabres prospect right now.

Their owner, Terry Pegula, poured millions into helping launch the Penn State hockey program, from which Bailey became the first player to score an NCAA goal and sign an NHL contract.

The connection seemed natural; the Sabres were also obviously well situated to add a prospect given their rebuild. Buffalo, for their part, thought they had him because of that connection.

But Bailey signed with the rival Maple Leafs.

To hear him tell it, Brendan Shanahan was one key reason why.

"The respect I have for him, his history," Bailey said. "He really just talked to me and told me the things he liked about my game and they're the same things I like about my game. I really think he's going to give me the chance to develop here."

It was only a 30 minute phone conversation, but it made a huge difference to an uncertain, young kid making his first foray into pro hockey.

A couple of things here. Shanahan – and really everyone with the Leafs – has taken a lot of heat as the team has nosedived in the standings, with eight wins in their last 43 games. One of the most common criticisms of the Leafs president is that he doesn't have experience in an NHL front office, as his post-playing role was with the league head office as disciplinarian.

That's fair. But what Shanahan does have is what few other high level NHL execs have, and that's a playing resume that's almost unmatched. He's in the Hall of Fame, he's 14th in career games played, 13th in goals scored, 25th in points and 22nd in penalty minutes.

He won three Stanley Cups and a gold medal in 2002 at the Olympics.

And Bailey, a kid who grew up a world away in Anchorage, Alaska, knows full well who he is. Anyone in hockey would.

The Leafs aren't the only team with that kind of clout in the front office. Ron Francis is now the GM in Carolina. Steve Yzerman has done a marvelous job in Tampa. And Luc Robitaille and Rob Blake are key cogs in LA.

Then there is Joe Sakic and Patrick Roy in Colorado, Trevor Linden in Vancouver etc.

But this is a new advantage for the Leafs, to have someone with Shanahan's background who's at the top of the organizational hierarchy and willing and able to talk directly to even a depth prospect – which is, let's face it, what an undrafted 23-year-old in his third year of college is – and win them over.

Bailey is expected to make his NHL debut on Thursday against the Florida Panthers, exactly one week after his college career ended with a loss in Detroit against Ohio State in the Big Ten Tournament. That was another thing the Leafs could promise, that they would get him in right away, but we have to be careful not to read too much into that.

It doesn't mean he's ready. It doesn't mean he'll be with the Leafs next year, either.

Former Leafs GM Brian Burke used to call free agents like Bailey found "wallets," a creative way of saying a free bet. The problem is that a lot of them don't turn out to be much more than depth AHL players, at best, as the likes of Spencer Abbott, Simon Gysbers, Christian Hanson and Brayden Irwin show.

But others, like Tyler Bozak and Ben Scrivens, turn into valued assets, and they're the kind of rare ones you get without having to expend even a late round draft pick, which are often little more than lottery tickets anyway.

The Leafs are in such a basic, foundational stage right now that they simply have to load up on as many of those tickets as they can get to set the groundwork for a rebuild. Prior to the trade deadline they added five draft picks – a first, second, fourth, fifth and sixth rounder – in the off-loading, meaning they'll have nearly a full draft's worth of selections added to their 2015 and 2016 haul.

Out of that, they're going to need to get some unlikely hits, finding useful players where other teams miss them.

That's where Mark Hunter and Kyle Dubas, two men just removed from junior hockey, come in, and both have been deeply involved on the scouting side since it became apparent that was going to be the Leafs focus come April.

Adding someone like Bailey – or Nikita Soshnikov, who they signed last week out of the KHL and will likely play for the Marlies next season – is a very small part of that, but it's an important part nonetheless.

And, in addition to their financial clout, the Leafs have another advantage working for them in trying to get them.

"I felt like after that conversation with Brendan [I knew]," Bailey said. "I wasn't sure about where I was going; there was a lot of options. The opportunity here and what he saw and what he said to me, it made me feel comfortable coming here."

Given how far away they Leafs are right now, they need to capitalize on as many of these "ins" as they can. They need to keep making bets, again and again – and the free ones are simply an added bonus.