Lacing Up is a weekly column taken from an email conversation between Ashley Gallant and CJ. “Stoosh” Jiuliante. Stoosh is a former Faceoff Factor staff writer and a long-time hockey fan.

Ash: Hockey’s biggest market, the Toronto Maple Leafs, hasn’t won the Stanley Cup since the Original 6 era and the future doesn’t look very promising. What’s wrong?

Stoosh: The future didn’t look very promising until this offseason. I think it’s finally become apparent to ownership that what they’ve been doing wasn’t working.

But what got them to this point? There are so many factors.

To me, it always seemed like they were more interested in buying a championship team rather than develop one through the draft. Toronto has always seemed to show less regard for draft picks than most teams. If you go back over their last fifteen drafts, five of them found the Leafs without a first round pick. Three of those have happened within the last six drafts.

To make matters worse, two of their last six first-round picks were traded – Brad Boyes (24th overall in the 2000 Draft) and Tuukka Rask (21st overall in the 2005 Draft). Boyes was packaged with Alyn McCauley and the Leafs’ first-rounder in the 2003 Entry Draft (which San Jose turned into Steve Bernier) for Owen Nolan in an attempt to gear up for the playoffs in 2002-03; that playoff run would last only seven games and Nolan lasted only one more year with the Leafs. Rask was traded in June of 2006 to Boston for goaltender Andrew Raycroft.

They threw a lot of money at veterans that were probably past their respective primes as well. They paid Ed Belfour $6.5M in 2002-03 and $7M in 2003-04 to be their primary goaltender despite the fact that he was into his late 30s. Owen Nolan cost them $5.5M in 2002-03 and $6.5M in 2003-04 (as well as Brad Boyes and the aforementioned first-rounder in 2003). For that investment, they got a whopping 26 goals and 34 assists in 79 total games. Think they wouldn’t rather have Boyes and Bernier back now?

Those are just a couple of examples, but their recent history is riddled with short-sighted moves like these.

Ash: You throw some very good examples of the mismanagement of the Leafs. It’s a little hard to build a Stanley Cup-winning team when you throw cash at veterans who have seen better days, or when you don’t have Detroit’s knack at drafting players, or when you trade away your draft picks for a bag of pucks.

I came across a few stats that clearly illustrates how ‘bad’ this team has been since 1967…at least in terms of how ‘un-great’ (I know that’s not a word) Leaf players have been. Since their last Stanley Cup, only two players have won NHL awards: Doug Gilmore won the Selke in 1993, and Alex Mogilny won the Lady Byng in 2003. Art Ross, Rocket Richard, Calder, Conn Smythe, Hart, Norris, and Vezina trophies? Zilch.

Now look at the Montreal Canadiens…they have won 11 Vezinas, 3 Norrises, 3 Harts, 7 Selkes, 8 Conn Smythes, 1 Calder, 1 Lady Byng, and 3 Art Rosses for a grand total of 37 individual awards.

Let’s see…2 vs 37…It kind of says something, doesn’t it?

One more thing: The Leafs have been mishandled for so many years, and I think a big reason why that hasn’t really changed is because there is no real pressure on the team to change. Think about it for a minute. If people stopped caring about the Leafs, stopped watching, and stopped buying everything with a Leafs logo, then the team would be forced to change their ways. But the fact of the matter is that every single game is sold out, companies are lining up to buy those luxury suites, there’s a 3 year waiting list for season tickets, e-v-e-r-y-t-h-i-n-g is available with a Leafs logo (a flip through the Sears Christmas catalog up here will confirm this), the Leafs are seen as ‘Canada’s team’, and a couple of tickets to a mid-week game against a team of ‘nobodies’ will cost you a few hundred dollars. All of this despite the fact that they haven’t won anything in over four decades.

Why bother changing?

Stoosh: The “why bother changing” is an interesting take on the whole Leafs situation. In a way, they kind of remind me of the Steelers, who are sometimes subjected to some criticism here because they aren’t usually big players in NFL free agency. When the Steelers don’t play well, you hear some accusations start to fly that the ownership is cheap, but this only really shows up when they’re losing. The big difference between the Steelers and Leafs is that the Steelers seem to have a clue as to how to draft and develop players within their organization, and therefore don’t feel the need to build through free agency.

The Leafs actually remind me more of the Yankees than anything else. They have a fan base that largely acts as if their team is entitled to championships and success simply because they’re the Leafs. The fan base is largely impatient, outspoken and demanding, which doesn’t help because the media picks up on this. Everything is scrutinized, criticized, and scrutinized again by the media and the fans. It turns everything around the team into some sort of mix between a pressure cooker and a circus. Players are under constant pressure to perform; management’s decisions are being questioned and examined from every possible angle.

Because money talked in the pre-lockout NHL and they had so much money to spend, the Leafs placed a low value on draft picks and prospects. They didn’t have time to develop prospects because the economics allowed teams with high revenues to build teams full of expensive, big-name talent. The Leafs would acquire a big name simply because the player was a recognizable name; it didn’t matter whether that player fit within a system or was willing (or able) to play a particular role. And that big name would cost them prospects, draft picks or both. If signings didn’t work out, it could be hidden by another big-name acquisition.

And when things eventually leveled off economically and teams couldn’t spend to try to build their teams made up of pricey free agents, the Leafs seemed to be afraid of what would happen if they asked their fanbase to remain patient for a couple of years so they could build up their depth and bring an elite player or two into their system.

After stinking up the joint and realizing that expensive free agents were much more likely to perform well under expectations set by their salary, it appears that they’re finally realizing that they need to develop a deep organization. They let go of several overpriced, low-return veterans, resisted the temptation to make a free agent splash just for the sake of signing someone this past summer and began to emphasize the development of prospects with the selection of defenseman Luke Schenn fifth overall in the 2008 Entry Draft. That looks to continue again this year, as they’re one of the early-season favorites to factor into the John Tavares/Victor Hedman sweepstakes.

If the fanbase is willing to be patient, it might actually pay dividends in a couple of years.