Could this be the year we finally see an NHL team shake up the RFA market with an offer sheet?

There’s been some debate over the weekend, spurred on by a post at The Athletic that argued that the Maple Leafs could take a run at someone like St. Louis defenceman Colton Parayko. In the piece, Tyler Dellow lays out the case for the Leafs to target a capped-out Blues team.

On the one hand, the idea seems crazy. Even putting aside whether the Leafs should be trying to fast-track their rebuild, offer sheets almost never work — there’s only been one successful attempt since 1997. But Dellow lays out a convincing argument that this year’s Leafs are a rare case of a team that could pull it off, because they have lots of short-term cap room, an obvious hole in the roster, and draft picks that are unlikely to fall at the top of the draft.

The entire discussion may be more of a theoretical exercise than anything, since Doug Armstrong claims the Blues would automatically match any offer sheet on one of their players. If so, he’d be falling in line with most of his colleagues through NHL history. The list of players who’ve signed offer sheets at some point in their career is longer than you might think, and some of the names are big ones. But the offer sheets are almost always matched.

So today, let’s break out some alternate history as we look back at some of the bigger offer sheets over the years and ask: What might have happened if the team hadn’t matched?

Michel Goulet, 1991

The offer sheet was still a relatively new weapon in 1991, having been in play for just five years, and at that point one had never actually been matched by the player’s original team. The Blues had pulled off what still stands as the most successful offer sheet ever in 1990, when they’d pried Scott Stevens away from the Capitals. A year later, they decided to try again.

Their first target was Goulet, a veteran sniper coming off his first full season in Chicago. Going after Goulet served a dual purpose for the Blues, who could land a decent scorer while hurting their arch-rivals in the process. The Blues and Hawks had battled it out for the Presidents’ Trophy in 1990–91, and Goulet’s offer sheet continued the rivalry. St. Louis offered the veteran a four-year deal worth nearly $3 million, but Chicago matched, and the Blues had to turn elsewhere.

What if?: Goulet would play three more years and score 61 goals; decent numbers, but not enough to really change the course of history for either team. (Although he did help the Blackhawks make the final in 1992.)

But there may have been a crucial side effect of the Goulet deal. Having missed on one winger, the Blues turned their attention to a bigger offer-sheet prize: New Jersey’s Brendan Shanahan. The good news is that they got him. The bad news is that it cost them far more than they imagined, when the Devils demanded Stevens as compensation. An arbitrator agreed, Stevens became a Devil (after a brief holdout) and the rest was history.

If the Blackhawks had let Goulet go to St. Louis, there’s at least a decent change that the Blues never target Shanahan. And that means Stevens doesn’t end up anchoring the Devils’ blue line for the next dozen years.

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Kevin Stevens, 1991

The Bruins and Penguins waged one of the better feuds of the early ’90s, spurred on by Cam Neely and Ulf Samuelsson. After the Pens knocked off the Bruins in the 1991 conference final, Boston decided to take the rivalry off the ice during the off-season by targeting one of the Penguins’ best young players with an offer sheet.

Bruins’ GM Mike Milbury gave the power winger a five-year deal reportedly worth over $1 million per season. The idea of Stevens, a local boy, playing on a line with Neely seemed irresistible. But after several days of suspense, the Penguins matched the offer.

What if?: Stevens scored 109 goals over the next two seasons and was a first-team all-star in 1992. The Penguins beat the Bruins in the conference final yet again that year, including a game in which Stevens scored four goals against his would-be team. Would the series have turned out differently if Stevens had been on the other side? It’s unlikely — it was a four-game sweep — but we’ll never know for sure.

Teemu Selanne, 1992

Here’s a trivia question that would stump most fans: Who did Teemu Selanne sign his first NHL contract with?

The answer: the Calgary Flames.

Yes, despite being drafted by the Jets in 1988 and making his NHL debut in Winnipeg four years later, Selanne actually signed his first deal with Calgary, in the form of an offer sheet. The Flames gave the Finnish rookie a three-year deal worth $2.7 million, nearly double what the cash-strapped Jets were hoping to pay.

It was worth a shot, but Jets GM Mike Smith quickly matched. Any lingering bad feelings were quickly forgotten when Selanne took the league by storm with a 76-goal rookie season.

What if?: One can only imagine when Selanne could have done playing alongside Theo Fleury, Gary Roberts and Joe Nieuwendyk. At the very least, you’d have to assume the Flames wouldn’t have gone a dozen years without winning a playoff round.

(Flames blog Matchsticks and Gasoline did a deep dive in to a Selanne-in-Calgary alternate universe here and here.)

Scott Stevens, 1994

No player was more linked with offer sheets than Stevens. He went from the Capitals to the Blues after signing one, and from the Blues to the Devils after Shanahan did. Most fans know about those two transactions. But not everyone remembers a third offer sheet run-in for Stevens – the time he tried to escape New Jersey by rejoining the Blues during the 1994 off-season.

The deal backfired badly on St. Louis when the Devils quickly matched, then accused the Blues of tampering. The case wasn’t settled until 1999, when the league found the Blues guilty and ordered them to compensate the Devils with draft picks and cash.

What if?: It’s hard to imagine the Devils winning three of the next eight Stanley Cups without Stevens; it’s possible they don’t win any. With all due respect to Martin Brodeur and Scott Niedermayer, Stevens may have been the most important player on those championship teams.

Here’s an extra layer: If Stevens winds up back in St. Louis in 1994, do the Blues still deal for Chris Pronger a year later? And if not, where does he wind up after wearing out his welcome in Hartford?

Keith Tkachuk, 1995

One of the key aspects of any offer-sheet attempt is to target a vulnerable team. And they don’t come much more vulnerable than the 1995 Winnipeg Jets, a team that was on the verge of moving, had new owners, and already needed to spend a big chunk of its meagre budget on resigning Selanne.

So it made sense for the Blackhawks to pounce with a five-year, $17-million offer to Tkachuk that would make him the league’s third-highest-paid player. Tkachuk playing alongside Chicago star Jeremy Roenick seemed like an unstoppable combination.

It was worth a shot, but the Jets matched the offer and Tkachuk remained in Winnipeg. Briefly.

What if?: Within a year, the Jets were on their way to Arizona. Ironically, Roenick would join them there after a trade, and he’d help Tkachuk lead the league with 52 goals in 1996-97. Meanwhile, the Blackhawks would win just one playoff round over the next 14 years.

Joe Sakic, 1997

We throw the term “franchise player” around a lot, but there’s no doubt it applies to Sakic and the Avalanche (and Nordiques). He spent his entire 20-year career with the team, and remains there to this day in the front office.

That makes it a little awkward to mention the time he signed with the New York Rangers.

But it did happen. Back in 1997, the Rangers were reeling after the departure of captain Mark Messier to Vancouver. So they looked to Sakic, signing the star centre to a three-year deal worth $21 million. To make things even tougher on the Avalanche, the Rangers front-loaded the contract with a $15-million signing bonus.

Colorado GM Pierre Lacroix raised a few eyebrows by taking the full week to make up his mind, but with a new arena on the way, he ultimately decided to keep his captain.

What if?: The Avalanche would continue to be one of the league’s best teams for years, including four trips to the conference finals and a Stanley Cup in 2001. Do they get that Cup without Sakic in the lineup? We’ll never know, but it sure seems unlikely.

As for the Rangers, they moved on to Plan B a few weeks later by trading for Pat LaFontaine. He’d only last one season in New York before injuries ended his career.

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Sergei Fedorov, 1998

The contract that Fedorov signed with the Hurricanes is one of the more bizarre in the history of the NHL, if not all of pro sports. As with most offer sheets to star players, it paid him a ton — $38 million over six years, including a $14-million signing bonus paid up front. But it was another bonus that stood out. The Hurricanes included an additional $12 million in bonuses over the life of the deal, with all of it to be paid immediately if Fedorov’s team qualified for the 1998 conference finals.

That bonus was clearly meant as a poison pill to prevent the Red Wings from matching. The Hurricanes hadn’t made the playoffs in six years, so their odds of a conference finals appearance were tiny. But the Red Wings were the defending Cup champs, and had made the final four in each of the last four seasons. Factoring in Fedorov’s salary on top of both bonuses, and the deal was structured so that the Red Wings would likely need to pay him a jaw-dropping $28 million for one season of hockey.

The league initially rejected the contract, but an arbitrator later ruled it valid. Mix in the fact that Fedorov had already held out for half a season and vowed to never play for Detroit again, and it seemed like the Wings might be stuck.

They weren’t. Ultimately, the Red Wings gritted their teeth and matched. Fedorov reported, the Red Wings did make the conference final, and the star center made more money in one year than any NHL player ever.

What if?: Take Fedorov off the roster, and there’s a good chance the Wings don’t repeat in 1998 — he led the league in post-season goal-scoring that year. Fedorov and the Wings would win another Cup together in 2002, this time over those same Hurricanes.

Ryan Kesler, 2006

Most of the offer sheets on this list went to established stars. But every now and then, a team will target a younger player who hasn’t broken out yet. That’s what happened in 2006, when the Flyers made a play for a 21-year-old centre with just 12 NHL goals to his name.

The offer sheet probably never had a chance – Kesler had been the Canucks’ first-round pick in 2003, and they’d only receive a second-round choice as compensation for letting him walk. It took just two days for the Canucks to match the offer, along with some grumbling about the Flyers messing with another team’s cap structure.

What if?: It’s not hard to pick a winner in this one. Kesler ended up developing into one of the best two-way forwards in the league, and was a key piece of the Canucks team that won back-to-back Presidents’ Trophies and came within a game of the Stanley Cup in 2011. Meanwhile, the Flyers bottomed out in 2006–07, finishing dead last.

For what it’s worth, the Canucks tried a similar move in 2008 when they signed young Blues’ forward David Backes to an offer sheet of their own. The Blues matched the offer, then immediately retaliated with an offer sheet to Vancouver’s Steve Bernier.

Thomas Vanek, 2007

The Oilers stunned the NHL when they offered Vanek $50 million over seven years. You could understand their logic — one year after being abandoned by Chris Pronger, they were desperate to reestablish themselves as a destination for star players — but the dollars were sky high for a guy who’d only played two seasons. Meanwhile, the Sabres had already lost Chris Drury and Daniel Briere to free agency, and pretty much had to match any offer that came in on Vanek. They did.

What if?: There are plenty of ways to go on this one. Vanek never really lived up to his contract, so maybe the Oilers dodged a bullet. And the Sabres would have received Edmonton’s next four first-round picks, two of which ended up being first overall.

But there are even bigger stakes in play here. If the Sabres don’t match the Vanek offer sheet, the Oilers probably don’t go after Dustin Penner two weeks later. That means we don’t get the only unmatched offer sheet of the cap era and — far more importantly — we never get the infamous story about Brian Burke wanting to fight Kevin Lowe in a barn.

Shea Weber, 2012

This one is by far the biggest offer sheet ever signed, and the only one that’s still in effect to this day. The Flyers went after Weber with both barrels, giving the two-time Norris runner-up a massive 14-year, $110-million deal that was packed with signing bonuses.

It was a contract designed to be unmatchable for the small-market Predators. But Nashville had already lost Ryan Suter to the Wild as an unrestricted free agent, and losing Weber too would have been devastating. After discussing the possibility of a trade, the Predators ultimately matched the offer.

What if?: You don’t have to stretch very far to see how this decision impacted the future since it’s playing out in front of us right now. Not only was Weber’s deal not unmatchable, it also turned out not to be untradeable, as we found out with last summer’s blockbuster P.K. Subban trade.

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Now, Subban and the Predators are playing for the Stanley Cup, while it’s the Canadiens who are left wondering about the long-term impact of Weber’s contract.

Ryan O’Reilly, 2013

This deal from four years ago still stands as the league’s most recent offer sheet, which gives you an idea of how rare they are in the modern NHL. But it was a big one, as the Flames tried to snag O’Reilly from the Avalanche with a two-year offer. The 22-year-old centre’s contract negotiations with Colorado had been contentious, and after trade talks had fallen through, the Flames made their move.

It didn’t take long for the Avalanche to respond. They matched the offer just hours after it had been filed. But as we were about to find out, that was only the start of the story.

What if?: The next day, Sportsnet’s Chris Johnston dropped a bomb: The Flames had nearly committed an enormous mistake. Because O’Reilly had played in Europe during the season, he’d have had to clear waivers before signing with a new team. That would have meant the Flames would have given up two draft picks, then immediately lost O’Reilly for absolutely nothing.

The Flames claimed that the rule wouldn’t have applied, although they didn’t sound especially convincing. Either way, the Avalanche saved the league from a major controversy by matching so quickly.

That may have helped the Flames in another way. If O’Reilly ends up in Calgary, it’s possible he helps them win a few extra games that season, moving them down the draft order and costing them the chance to take Sean Monahan with the sixth-overall pick. It’s fair to say that all things considered, Flames fans are probably pretty thankful that the Avalanches matched.