Sports fans are a masochistic bunch, and there’s nothing we love more than to torture ourselves with hypotheticals from the past. What if Player X was on my team? What if they scored that goal in the dying seconds? What if my GM made this move 13 years ago? This is a series that will indulge that painful fantasy, by taking the best What If scenarios from hockey and going as deep down the rabbit hole as possible. Some of these will be funny. Some will be painful. Others will be enlightening. Hopefully some will be all three.

Today's What If Scenario: What if Vincent Lecavalier was traded to the Maple Leafs in the 2013 offseason?

Coming out of the 2012 lockout, the NHL and NHLPA agreed that, as part of the new CBA, each team would be granted two "compliance buyouts" until the end of the 2013-14 season. In order to meet the lower salary cap following the lockout shortened season, each team would be allowed to buyout two players without any cap penalty. Naturally, this lead to two entertaining offseasons that saw historically large buyouts such as Rick Dipietro, Brad Richards, and Ilya Bryzgalov. But the most hand-wringing and drama was saved for what would stand as the most expensive buyout in NHL history: Vincent Lecavalier’s $32 million payday from the Tampa Bay Lightning.

Lecavalier had been arguably the Lightning’s franchise player since being drafted 1st overall in 1998. He had been granted the captaincy twice over, won the Stanley Cup with the team in 2004, and was at one point considered by some to be among the best players in the league. In July of 2008, just after the Lightning had bottomed out and drafted Steven Stamkos 1st overall, Lecavalier inked an 11-year, $85 million contract following 52 and 40-goal seasons, to kick in the following season. Unfortunately, things just went downhill from there. Lecavalier never topped 30 goals or 70 points again, and even before the contract kicked in there was talk of moving him (including a deal to the Habs that may have included Carey Price, PK Subban, and Max Pacciorretty, although this is disputed).

Lecavalier was never terrible in the seasons between his signing and his buyout — he scored 19 points in 18 games in the Lightning’s 2011 run to the Conference Final, and managed a respectable 32 points in 39 games in the 2012-13 season. But with the Lightning finishing an abysmal 28th overall, and staring down the barrel of seven more seasons of paying $7.7 million for declining production, the team was eyeing the amnesty buyout closely. Still, this was their captain and the first superstar the team had ever had, and they would have loved to keep him on at a lower salary. Unfortunately, the rules prevented a team from resigning a player they had bought out for at least one year. But GM Steve Yzerman thought he spotted a loophole, and all he needed was a team with a lot of money. Enter the Toronto Maple Leafs, fresh off their first playoff appearance in nearly a decade and in a fairly decent cap situation. The two teams hatched a trade that would see Lecavalier traded to the Leafs along with an asset (reportedly the 3rd overall pick in the 2013 draft), and in exchange the Leafs would use one of their amnesty buyouts, allowing the Lightning to resign Vinny at a better rate. A win for everybody! Except the NHL, which saw it as a circumvention of the rules and nixed the trade.

The rest is history, especially for Leafs fans, who saw the team use their buyout on Mikhail Grabovski and then give that money to David Clarkson. Vinny was bought out and went to the Flyers on a 5-year deal, which quickly became almost as much of a headache as his previous contract.

What if the NHL had allowed that trade?

June 26th, 2013

Leafs GM Dave Nonis announced today that the team had acquired Vincent Lecavalier and the Lightning’s first round selection in the 2013 NHL draft in exchange for the Leafs’ fifth round selection in the 2013 NHL draft. It’s expected that the Leafs will buy out the remaining seven years and $52 million of Lecavalier’s contract, which will allow the Lightning to resign their long time captain and franchise player.

There were rumblings that the league was unhappy about the trade, but begrudgingly allowed it on the grounds that it was not technically against the rules. Lightning GM Steve Yzerman declined to comment on the trade, but it is widely believed that the team will tender an offer to Lecavalier on July 5th, if they have not agreed to a deal already.

July 30th, 2013

The first round of the 2013 NHL draft wrapped up today, with the Avalanche selecting Halifax Mooseheads center Nathan Mackinnon first overall. In a surprising move, the Florida Panthers passed on Portaland Winterhawks defenseman Seth Jones, who had challenged Mackinnon as the top-ranked prospect, instead selecting Alexsander Barkov with the second overall pick.

Jones was selected third overall by the Toronto Maple Leafs, who had acquired the pick from the Tampa Bay Lightning along with Vincent Lecavalier, who’s contract was bought out yesterday by the Leafs under the amnesty buyout rules. Giving up the third overall pick was a bitter pill to swallow for the Lightning, who would have no doubt loved to take sniper Jonathan Drouin as a future winger for Steven Stamkos. Sources close to the team said that they saw Drouin as a potential first liner as soon as next year.

The Leafs were delighted to draft Jones, although it was unexpected as the team planned on drafting either Drouin or Barkov, being short on top forward prospects but already having a potential number one defenseman in Morgan Reilly. Still, the team envisions both players to be a potential top pairing in the years to come, according to sources close to GM Dave Nonis.

The Nashville Predators went with Sean Monahan at number four, which was viewed by some as an off the board pick. "There were a lot of great players to choose from, but the organization felt it was best to target a player we believe can develop into a number one center," GM Dave Poile said of the pick. "Of course, you take the best player available, but unless there was a huge surprise that fell to us at number four, we knew who we wanted."

Drouin would not fall much farther, as the third-ranked prospect was snatched up by the Carolina Hurricanes at number five. "We see Jonathan as a guy with the potential to play on our first line for a long time," said Hurricanes GM Jim Rutherford. "We don’t know when yet, but he may still require some development in the lower leagues. Hopefully he’s willing to be patient if that ends up being the case."

July 5th, 2013

Following a round of amnesty buyouts last week, it was a whirlwind of free agent signings today, as teams spent their newly acquired cap space freely. The biggest contracts went to hard-nosed wingers Nathan Horton, who signed a 7-year, $37 million contract with the Columbus Blue Jackets, and David Clarkson, who signed for 7 years and $40 million with the Edmonton Oilers.

"We are delighted to have David join our team," said Oiler’s GM Craig Mactavish, whose team has often had trouble attracting big name free agents. "With a stronger finish this past season and the addition of a veteran, heart and soul player like Clarkson, a new era is beginning for the Oilers."

Sources close to Clarkson said he had reached out the Toronto Maple Leafs about a contract, expressing a desire to play for his boyhood team. The team considered an offer, but found Clarkson’s demands too rich, as they chose instead to re-sign center Tyler Bozak to a five-year deal. With four years and $22 million tied up un Mikhail Grabovski, and new contracts due in the future for Nazem Kadri, Phil Kessel, and Dion Phanuef, the Leafs were unable to make the commitment that Clarkson was looking for.

As expected, the Lightning signed Vincent Lecavalier to a five-year, $20 million contract. Lecavalier was traded to the Leafs last month, who used their amnesty buyout on his contract, garnering them Seth Jones in the process.

Other notable free agents signings included Daniel Briere, who inked a four year deal with the Habs, and Valteri Filpulla, who signed for five years with the Flyers.

May 24th, 2014

The Edmonton Oilers today announced that they have parted ways with long GM Craig Mactavish, following a disappointing season which saw the team finish 28th overall, after appearing to take a step forward the previous season. While the goaltending of Devan Dubnyk and a lack of help on the blueline doomed the Oilers’ season, there was perhaps no bigger disappointment than David Clarkson. After signing a massive, $40 million contract in 2013, the 29-year old former 30-goal scorer took a larger step back, managing only 11 goals and 21 assists on the season, while missing significant time with injury. Clarkson’s season started off on the worst possible note, as he was suspended for the first 10 games after jumping off the bench to fight in a preseason game against the Winnipeg Jets.

May 5, 2015

Big news around the NHL today as the Minnesota Wild fired head coach Mike Yeo following a disappointing season for the Wild in which they missed the playoffs for the first time in three seasons. GM Chuck Fletcher was reportedly reluctant to fire Yeo, who had been with the Wild since 2011, as the team continued to display the strong puck possession game that Yeo had instilled, which had earned him a three-year extension in the offseason. Unfortunately for the Wild, it was not enough to combat the lackluster goaltending of Darcy Kuemper and backup Niklas Backstrom, as the Wild had a team save percentage of just .906, 29th in the league.

Oiler’s GM George McPhee held an end of the season press conference today, reflecting on his first season at the helm of the floundering Edmonton team, which saw them take a significant step forward. The Oiler’s biggest surprise (aside from a shocking trade in February in which they unloaded David Clarkson on the Columbus Blue Jackets in exchange for the perma-injured Nathan Horton) was Devan Dubnyk. After being traded by the Oilers in January 2014, Dubynk was brought back by the McPhee regime, who sent him for training at the NET 360 goaltending camp in Kelowna, BC. Dubynk’s turnaround has been one for the ages, posting a .927 save percentage and a 2.35 GAA with the Oilers, likely earning him some Vezina love this year. While it wasn’t enough to get the Oilers into the playoffs for the first time since 2006, their 18th place finish represents a big step forward in the development of the team. The other pleasant surprise for the Oilers was Taylor Hall, who scored 21 goals and added 39 assists in 53 games before going down with an ankle injury for the remainder of the season. Despite the injury, McPhee had high praise for Hall, calling him "a cornerstone of this franchise for a long time to come."

Meanwhile, Connor McDavid and the Erie Otters are off to the OHL final after trouncing the Sault St. Marie Greyhounds in Game 6, winning 7 to 3. McDavid scored once and added four assists, continuing the torrid scoring pace for the 18-year-old prospect, unanimously expected to go first overall in the 2015 NHL Draft.

The youngster’s play is being watched heavily from Toronto, where the club’s disastrous season turned into a windfall, winning the draft lottery and jumping ahead of Arizona and Buffalo for the right to draft the Toronto-born, potential generational player. McDavid will take the sting off a season with few positives — save the progress of the Reilly-Jones defensive pairing — that saw the Leafs fire head coach Randy Carlyle in January and plummet in the standings to finish the season.

Still to be seen is whether McDavid will be enough to lure Mike Babcock to Toronto. It is rumored that Babcock has narrowed the choice down to staying in Detroit or going to the Sabres. Contributor Mike Harrington weighed in, saying that he was confident Babcock would be coming to Buffalo for the upcoming season. "I think he and Detroit have had enough of each other, and I don’t think the Leafs getting McDavid will change his mind on the issue," Harrington said. "After all, Eichel is probably just as good if not better, and the Sabres are still far ahead of the Leafs in terms of the rebuild."

"If he doesn’t come to Buffalo, I’d be very curious to know why. I’ll be the first one at the press conference in Toronto if that happens."

January 25, 2016

The tense situation between the Carolina Hurricanes and prospect Jonathan Drouin continues without an end in sight, as the forward prospect has not rescinded his trade request from November. Drouin's agent, Allen Walsh, has expressed his client's disappointment with his lack of playing time with the Hurricanes. Drouin has spent all but two games this season playing with the Charlotte Checkers in the American Hockey League.

"Jonathan doesn't feel like he's being utilized in a way that is good for his development, or for the Hurricanes," Walsh said. "We could understand the situation if he was being kept off of a contending team like the Blackhawks or the Lightning, but the Hurricanes could really use him right now and it's simply ridiculous that he's not with them."

June 29, 2016

It was a moderately eventful 30 minutes in the NHL today that saw one big trade and another medium sized one. The big news was undoubtedly the trade that saw Montreal send PK Subban to Nashville in exchange for Shea Weber, which many are saying was due as much to Subban’s off-ice issues as the Habs struggles this season. Neither Habs GM Marc Bergevin nor Predators GM David Poile have spoken publicly yet, but both are expected to address the media later tonight. From Nashville’s point of view, the trade is certain to help alleviate an age problem on their blueline, which was trending towards 30 and lacking any young defenders.

That over shadowed the more subdued trade between Edmonton and New Jersey, in which the Oilers sent winger Jordan Eberle and a second round pick in the 2017 Draft in exchange for defenseman Adam Larsson. The reaction in the hockey world was surprise, but most experts say the trade makes sense from both standpoints. The Oilers are in danger of stagnating, having missed the playoffs narrowly again, and need to shore up the defense to go along with a developing offense and support superstar goalie Devan Dubnyk. In Larsson, they get a solid defenseman, albeit not a true first pairing defender. It was rumored that GM McPhee was willing to go higher for a blue liner with more upside, and even reportedly listened to offers on Taylor Hall. However, the team shut down that talk relatively quickly. "A player like Taylor doesn’t come around very often, and we’re not just looking to give him away without get a proper return," a source close to the Oilers said.

Looking ahead to Saturday’s free agency, the rumours are that Detroit, Buffalo, and Boston are vying for the services of David Backes, the top UFA center available, although there are some decent consolation prizes in Frans Neilsen, as well as the recently bought out Valteri Flipula and Mikhail Grabovski, although the latter’s concussion troubles may scare off some teams. It’s another free agency period without a big name, and next year promises more of the same, as we can report that the Lightning are going for a repeat of locking up a big name player early, with Victor Hedman set to sign an extension on July 1 to kick in 2017-18. The team locked up top center Steven Stamkos on July 1 last year, despite some rumblings that he would want to explore free agency. Stamkos credited veteran captain Vincent Lecavalier with convincing him to stay in Tampa Bay, arguing that GM Yzerman was a guy who would treat his players right. Even as his production has declined, the leadership role has been one that Vinny has been happy to play. Two seasons ago, he reportedly fixed the fractured relationship between Yzerman and veteran Martin St. Louis after the Olympic roster controversy. St. Louis was hours away from being traded to the Rangers at the 2014 trade deadline before Lecavalier convinced him to rescind his request. Though St. Louis is no longer with the team, having retired after the Lightning lost in the Cup final to Chicago last year, the Lightning are probably happy to have kept him, especially as the trade was rumoured to include Ryan Callahan, who’s six-year, $35 million deal is off to a bad start in Vancouver.

Finally, there is still no word on what the Blue Jackets plan on doing with head coach John Tortarella and center Ryan Johanssen, whose feuding was the focal point of an abysmal season that saw the Blue Jackets finish last overall. Columbus will be loath to part with Johanssen, although there were reports in January that he was nearly traded to Nashville in exchange for Ryan Ellis. Nashville declined the trade in light of Sean Monahan’s emergence, culminating in a 35-goal campaign for the 21-year old center. Johanssen has expressed a desire to stay with the Blue Jackets, but with Columbus drafting Auston Matthews first overall at the 2016 Draft last weekend, the 24-year old center might be expendable if the feud can’t be resolved.