Brian Burke's five-year rebuild that wasn't supposed to take five years is taking longer than expected.

The last time the Toronto Maple Leafs rebuilt, it was quick and almost painless. The team missed the playoffs only twice—in 1997 and 1998—but would become a post-season mainstay for the next six years.

But that mid-90s rebuild did not happen in one fell swoop—the three biggest trades actually occurred over a five-year period—and could be better characterized as a slow core replacement, rather than a fire-sale.

After bowing out of back-to-back conference finals, the Leafs began a process of turning their three most important players—Doug Gilmour, Wendel Clark, and Felix Potvin—into what should have been a strong group to build around in the future.

In Wendel Clark's case the return was overwhelming, but the players that came back in other trades were bungled away.

The Leafs still became a perennial contender in the late-90s and early-2000s, largely thanks to successful plunges into free agency, but poor asset management and pure, dumb luck ruined the rest of what should have been an overwhelmingly successful rebuild.

Since the Ottawa Senators entered the league as an expansion team in 1992-1993 they have won four division titles, one President’s Trophy, and made one Stanley Cup Final. They consistently topped 100 points a season and were a league powerhouse, albeit one that routinely fell short of expectations in the playoffs (“here’s Nieuwendyk again…scores again!”). Think of them as San Jose East.

However, the Sens put all that playoff baggage behind them when they made it all the way to the Stanley Cup Final in 2007 before being ousted by the Anaheim Ducks. In a little less than four years the Senators went from a Stanley Cup finalist to the disaster you see before you. What happened? Where did it all go so horribly wrong?

I was going to wait to post this until closer to the trade deadline, but since Burkie and Sutter have gone crazy I thought it was appropriate to post it sooner.

GMs of terrible teams look fondly upon the 2007 trade deadline with the same wistful eyes that cocaine dealers get when remembering the 1980s.

This is the trade deadline that made rebuilding even more difficult than it already is. That’s because the 2007 trade deadline is better characterized as the year of overspending or the year of ignorance. Since it was only the second year after the lockout teams didn’t quite realize the tremendous value of draft picks in a cap system, especially first round picks. When you commit a large sum of your cap space to a small group of core players you continually need to replenish your remaining roster spots with young, cheap talent. Having young players make meaningful contributions, while still on their rookie contracts, is essential. GMs who believed they were on the cusp of a Stanley Cup run, or worse, on the cusp of only the playoffs, traded their picks faster than a crack addict selling their sex.