Not so long ago, Tomas Kaberle was the only bright light during increasingly dark times in Toronto.

With the Leafs attempting to rebuild, Kaberle's name was linked in just about every trade rumour imaginable. Finally, after what seemed like years of endless rumours, Kaberle was dealt to the Boston Bruins for Joe Colborne, a first-round pick, and a conditional second-round pick, which eventually went to Toronto after Boston won the 2011 Stanley Cup.

However, Kaberle has been involved in trade talks long before Brian Burke struggled to bring respectability back to Toronto. Here are five major trades that would have seen Tomas Kaberle packing his bags and the history of the Toronto Maple Leafs change dramatically.

Eric Lindros

In March 2000, Eric Lindros suffered his second concussion of the season, the fourth of his career, and criticised team trainers for letting him play through concussion symptoms weeks earlier. GM Bobby Clarke stripped Lindros of his captaincy and the hatred between the two boiled to new heights.

Lindros eventually came back for Game 6 of the Eastern Conference Final against the New Jersey Devils. Many believed he was being rushed back out of desperation, as the Flyers were in the process of choking away a 3-1 series lead. In Game 7, Scott Stevens delivered what would become one of the most devastating hits of Lindros’ career, causing yet another concussion.

Still mad over the way he was handled by the team and its trainers, Lindros was dealt a low blow in the off-season as he was only offered a two-way qualifying offer that could see the Flyers dump him in the AHL. Lindros demanded a trade to his hometown Maple Leafs and sat out the entire 2000-01 season.

Talks between the Leafs and Flyers were contentious, mainly because Clarke didn’t actually want to make Lindros happy by trading him to his preferred destination. Miraculously, the talks progressed to a point that the Leafs and Lindros had agreed to a five-year, $45 million contract, but two separate deadline deals fell apart.

One deal was Nik Antropov, a few years removed from being the 10th overall pick, Dmitry Yushkevich, the Leafs’ No. 1 defeceman, and an undisclosed player.

Another deal was Antropov, 24-year-old defenceman Danny Markov, and a first-round pick.

However, the Flyers insisted upon 22-year-old Tomas Kaberle. The Leafs refused and the Flyers ultimately dealt Lindros to the Rangers for a package of Jan Hlavac, Kim Johnsson, Pavel Brendl, and a third-round pick.

Of course, the Leafs did eventually land Lindros for the 2005-06 season. But by that time he was a shell of his former self and was one year away from retiring. If the Leafs had made the trade with the Flyers, the 2005-06 season would be the last of Lindros’ $45 million contract, and with a salary roll back, Toronto would be paying Lindros $6.84 million to score 22 points in 33 games.

Vincent Lecavalier

After being nearly traded for Eric Lindros in 2001, Kaberle found himself involved in discussions for another No. 1 centre later that year. 

Vincent Lecavalier had yet to live up the hype of being a first overall selection, and was nowhere close to fulfilling the "Michael Jordan of hockey" moniker that former Lightning owner Art Williams bestowed upon him.

Lecavalier scored 146 points in 230 games over his first three seasons, and was struggling mightily in his fourth season (he scored 37 points in 76 games). The Lightning had about enough, especially as Lecavalier and head coach John Tortorella butted heads, and were ready to deal the 21-year-old to the Toronto Maple Leafs in December 2001.

The deal was Lecavalier to Toronto in exchange for Nik Antropov, drafted nine spots behind Lecavalier in 1998, Tomas Kaberle, Jonas Hoglund, and either recently drafted Brad Boyes, or Toronto's first-round pick in 2002 (Alex Steen).

According to Bill Watters, Toronto's assistant GM, the deal was complete. However, Tampa Bay GM Rick Dudley couldn't get Lightning ownership on board and the trade was never made.

Lecavalier broke out big the next season, scoring 33 goals and 78 points, the first of five consecutive seasons of 30+ goals. Lecavalier was a huge part of Tampa Bay's 2004 Stanley Cup victory and also won the Rocket Richard Trophy in 2006-07.

Chris Pronger

Following a storybook run to the Stanley Cup Final in 2006, the Edmonton Oilers were faced with the unsavoury task of dealing Chris Pronger, the No. 1 defenceman they had just acquired one year earlier and one of the main reasons they were within one game of hoisting the Stanley Cup.

Pronger cited personal reasons for asking out of Edmonton, and many speculated his wife was not happy living in the capital of Alberta.

The Leafs were coming off a year in which they narrowly missed the playoffs, thanks to the New York Islanders (of all teams), who defeated the New Jersey Devils in a shootout. That started the string of playoffless springs that Toronto still endures.

With Bryan McCabe about to sign a five-year contract, John Ferguson Jr. discussed bringing Pronger to Toronto. The initial offer was Kaberle, who himself just signed a fresh contract, and Matt Stajan, who scored 27 points as a 22-year-old. The Oilers insisted Alex Steen be a part of the package over Stajan, as Steen, a former first-round selection, was coming off a 45-point rookie season.

Ferguson would not part with both Kaberle and Steen, and the Oilers dealt Pronger to Anaheim for Joffrey Lupul, Ladislav Smid, and three draft picks.

Pronger helped Anaheim win their first Stanley Cup and JFJ was fired within a matter of years.

Jeff Carter

Cliff Fletcher rode into town in 2008, looking to crack skulls and move out bodies, after Leafs management mercifully cut JFJ loose years after they should have. On the docket was shipping out as many players as possible to give a clean slate, and refreshed prospect cupboard, for Brian Burke, who was heading to Toronto in the worst kept secret of all-time.

One of the major deals on the table for Fletcher was Jeff Carter, in the midst of what would be a 29-goal season, and a first-round pick for Tomas Kaberle. Fletcher was probably drooling at the thought, but Kaberle nixed the idea, using his no-trade clause to stick around in Toronto with the rest of his NTC-havin’ buddies.

Carter broke out huge the next season, scoring a career-high 46 goals and 84 points.

Especially with Mats Sundin leaving after the season, Carter was, and still is, the No. 1 centre the Leafs desperately needed.

The first-round pick turned into Luca Sbisa, which isn’t anything special, but at the time could have given Toronto more flexibility to make other deals.

Phil Kessel

Heading into his first off-season as the Leafs’ GM, Brian Burke was looking to make a splash. He targeted Phil Kessel of the Boston Bruins, who was being squeezed out of Beantown after a 36-goal season because Boston was so close to the salary cap. They were close to the cap because they signed Derek Morris to a $3.3 million contract (Morris wouldn’t even finish the season in Boston).

The two sides were close to a trade at the 2009 draft, but it fell apart because of a simple miscommunication. Boston GM Peter Chiarelli thought he was dealing Phil Kessel to Toronto for Tomas Kaberle and the seventh overall pick; Burke thought he was trading Kaberle for Phil Kessel and Boston’s first-round pick. Whoops.

When the two men realized the deal they thought they were getting wasn’t actually offered, the trade fell apart.

Toronto drafted Nazem Kadri seventh overall and the Bruins took Jordan Caron 25th overall.

With the threat of an offer sheet looming (which would have cost Toronto a first, second, and third-round pick), the two sides finally struck a deal a few months later. Toronto sent two first-round picks, which turned out to be the second and ninth overall, plus a second-round pick, for Kessel.

If Burke had agreed to the initial “offer”, he could have had Kessel for Kaberle and Kadri. So instead of Kessel, Kadri, Joe Colborne and Tyler Biggs, the Leafs would have Kessel, Tyler Seguin, and Dougie Hamilton. Are you sufficiently sad yet?

Burke must have erroneously believed the Leafs would improve substantially with Kessel, thus any picks he was dealing would have been expected to be higher than seventh. In addition, he must have believed he could get a first-round pick, plus a top prospect (first-round quality) for Kaberle (which he did). So, at the time, dealing Kaberle and the seventh overall pick must have looked liked three first-round picks to Burke, so two firsts and a second (which he probably thought would be closer to mid-round than lottery) would sound like an “underpayment”. But even with mental gymnastics, knowing who Toronto eventually gave up, it’s almost impossible to say Burke didn’t severely overpay.

To recap: Tomas Kaberle was almost dealt in five major deals; three times for a No. 1 centre, once for a No. 1 defenceman, and once for a No. 1 winger (with the added benefit of keeping a No. 1 centre in Toronto). For various reasons, none ever came to fruition and Leafs fans instead cling to faint hope that the package they did receive can someday erase the ghosts of the past.