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.

Mats Sundin

Obviously, the best player the Leafs received when they began disassembling the back-to-back conference championship-making team was Sundin, who replaced Clark in a shocker of a trade.

I don't need to take too much time explaining that Sundin was amazing, probably one of the best centres in Leafs history. A Hall of Famer.

The trade was pretty much the gold standard for any rebuilding trade. Exchange a veteran coming off a strong year for an up-and-coming superstar. Simple!

The initial hope was that Sundin himself would be enough to keep the Leafs competitive. However, missing the playoffs in two of the next three seasons made it apparent that the roster was in need of more. Cue Gilmour's exit. Two of the most beloved Leafs in team history gone within a few year's span.

Gilmour was packaged with defenceman Dave Ellett and sent to the New Jersey Devils in exchange for 22-year-old Steve Sullivan, 23-year-old Jason Smith, and 19-year-old prospect Alyn McCauley.

In this case, the Leafs got three quality pieces back from the Devils, but unlike with Clark trade, the team wasted all of them.

Jason Smith

Smith spent roughly three seasons in Toronto before being inexplicably shipped out to Edmonton for two second-round draft picks in 1999. What's truly puzzlingly about this move is that the Leafs were no longer a bad team by the time of the trade in 1998-99; they finished the season fourth in the East. So why move a 25-year-old defenceman for draft picks?

Smith flourished in Edmonton, slotting comfortably as the team's No. 3 defenceman, logging heavy penalty kill minutes. He was a steady presence, a punishing hitter, and someone who wasn't afraid to block shots. He was so well respected in Edmonton that he was named captain from 2001-2007.

He was the exact player the Leafs could have paired with Dmitry Yushkevich to create a true shutdown tandem, something they never really had during the Sundin era. Adding Smith would have helped solidify the backend. Those Leafs were at best an average defensive team, and one that relied almost exclusively upon Curtis Joseph and, later, Ed Belfour to keep the goals against down.

Keeping Smith would have also made trading for Cory Cross later in 1999 unnecessary, meaning Fredrik Modin, a power forward who averaged close to 25 goals a year in the six seasons after leaving Toronto, would still be with Toronto. There was a reason Mats Sundin didn't have any wingers to play with. Speaking of...

Steve Sullivan

The second screw up was even more indefensible. At least the Leafs received a pair of second-round picks for Smith (although they amounted to nothing). They let Steve Sullivan go for nothing.

Toronto unceremoniously dumped Sullivan seven games into the 1999-2000 season after he scored a respectable 40 points in 63 games. They dumped him to pick up Dmitri Khristich, who became a UFA after Boston decided not to accept the $2.8 million he was awarded in arbitration.

After being picked up off waivers by Chicago, who upped his ice time by almost six minutes from what he was playing in Toronto to start the year, Sullivan scored 64 points in 73 games. The first of seven straight seasons he would break the 60-point mark. In comparison, Khristich scored 39 points in 80 games for the Leafs over two seasons and was out of the league two years after leaving Toronto.

It wasn't like Sullivan had been bad in Toronto, either. He scored 85 points in 155 games with the Leafs over parts of four seasons, which amounts to 45 over 82 games. That average would have him in the top-five in team scoring. And he was still only 25-years-old with loads of potential. If the Leafs truly needed Khristich (who to be fair was coming off a 70-point season) they should have dumped someone like Kris King, who was 33 and was just barely able to take a regular shift.

The Leafs were able to cover up these mistakes by dipping into the free agent pool so successfully, but unnecessarily losing players like Smith and Sullivan forced them to deal quality pieces like Fredrick Modin and Danny Markov for depth up front and on the back end.

Alyn McCauley

McCauley suffered a concussion early in his career in Toronto, and never really blossomed into anything more than a fourth line centre. But he did have a huge playoffs in 2002 that helped the team reach the Eastern Conference Final. With Sundin out for long stretches of time with an injury, McCauley stepped up and scored 15 points in 20 games.

McCauley was eventually dealt by the Leafs in a package that included first-round pick Brad Boyes, in addition to another first-round pick, for San Jose winger Owen Nolan.

At best McCauley was a third line centre, so his loss wasn't something to lament, but I included him because he was a part of the Gilmour package.

One of the hardest losses, however, came from the player acquired for Felix Potvin, the last holdover from the magical 1993 team.

Bryan Berard

After a chance encounter at the grocery store between Ken Dryden and Don Meehan led to Curtis Joseph donning the blue and white, Potvin was shipped to Long Island in January 1999 for former first-overall pick Bryan Berard (thanks, Mike Millbury).

Berard was raw defensively, but his offensive, puck-moving talents were apparent. Through his first two-and-a-half seasons he scored a point almost every other game, and continued that pace as a 21-year-old on Toronto's blueline.

At this point, the Maple Leafs should have had a young, capable defence core, one mixed with stay-at-home defencemen—Yushkevich, Smith, and Danny Markov—and puck-movers—Tomas Kaberle, Berard, and soon Bryan McCabe (laugh, but back then McCabe was for some reason allowed to use the can-opener and was actually solid). All of those defenceman would have been under 30, and the oldest, Yushevich, was only 28.

Instead, Smith was in Edmonton and Berard nearly lost his eye in a freak high sticking accident at the hands of Marian Hossa. Although Berard returned to the league a few years later, he did so with the New York Rangers, and was not the dynamic player he was on the verge of becoming in Toronto.

So what should have been a strength for the Leafs, turned into a liability. Over the years players like Cory Cross, Dave Manson, Aki Berg, and Jyrki Lumme sucked up minutes they should not have been given. And Bryan McCabe and Tomas Kaberle took on harder defensive responsibilities, which could have been better handled by someone like Smith.

The offense during that era was always strong, being in the top-5 on four occasions, but could have still benefitted from two additional top-6 forwards, Sullivan and Modin.

For a team struggling so mightily to rebuild today, fans can only look back and wonder what might have been if the Leafs took full advantage of how successfully they transformed their team years ago.