Top 15 HUGE NHL Free Agent Signings That Almost Happened

Aside from the Stanley Cup Playoffs and the trade deadline, there is perhaps no time of the year more exciting in the NHL than free agency. While "Free Agent Frenzy" definitely isn't what it used to be, thanks to the salary cap, fans still get excited in seeing who will change teams and to see if their team will land a new star.

Before the days of the salary cap, free agency was a lot more wide open. Teams were willing to spend, especially big market teams. Another dimension of free agency that isn't explored much today was offer sheets. Today, it has become taboo for NHL GMs to go after RFAs, as they risk losing a team as a future trading partner. With the increased importance of draft picks today, it also has caused teams to be less willing to pay the price of draft picks in signing other teams' RFAs.

This list today will explore past players signing offer sheets with other teams, only for their original team to match the offer, nixing any potential free agent signing. It will also show you past UFAs and who they almost signed with. With all that explained, here are 15 huge NHL free agent signings that almost happened.

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15 Ryan O'Reilly To Calgary

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This is the most recent example of an offer sheet signing, and it just shows you how rare it is today. Coming off the 2012-13 NHL lockout, Ryan O'Reilly still remained unsigned by the Colorado Avalanche with the shortened season in full swing. Sensing that a long-term offer wouldn't be going O'Reilly's way, the Avs' division rival Calgary Flames took a shot at prying the two-way center away, signing him to an offer sheet of two years, worth $10 million.

The Avs and O'Reilly would continue to have squabbles over money and the Avalanche eventually traded O'Reilly to the Sabres with Jamie McGinn for Nikita Zadorov, Mikhail Grigorenko, J.T. Gompher and a first round pick. You have to wonder if the Avs would have been better off taking the compensation from Calgary.

14 Mats Sundin Nearly Ends His Career In New York

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Mats Sundin began his career with the Quebec Nordiques, but by the time the end of the 2008-09 season ended, his legacy was cemented as perhaps the greatest Toronto Maple Leaf of all time. However, with the Leafs five years removed from a playoff appearance, it was obvious Sundin wasn't going to win a Stanley Cup in Toronto. With Sundin about to become a free agent, the Leafs gave the Canadiens exclusive negotiating rights to Sundin prior to July 1st. After that deadline passed, Sundin also received offers from the Canucks and the Rangers. Sundin decided to sit out the first half of the 2009-10 season, as he was mulling retirement.

In December, Sundin's decision was down to the Rangers and Canucks. Finally on December 18, 2008, Sundin chose to sign a one-year, $8.6 million deal with the Canucks. He would retire following the 2008-09 season.

13 Thomas Vanek To Edmonton

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Thomas Vanek recorded his best statistical season in 2006-07 and the timing couldn't have been better. Vanek was set to become a RFA and he picked a good time to record an 84-point season. His production got him a seven-year, $50 million offer sheet from the Edmonton Oilers, which Vanek signed. This put the Sabres in a very tough spot, because they had already lost two stars in free agency that year; Daniel Briere and Chris Drury.

Sabres GM Darcy Regier and Oilers GM Kevin Lowe then had a very public feud, as Regier was livid that Lowe tried to poach Vanek. The Sabres would continue to get productive years out of Vanek while the Oilers continued to wither away. It just goes to show you how frowned upon giving offer sheets is.

12 Ryan Kesler To Philly

Sergei Belski-USA TODAY Sports

Due to the 2004-05 season getting wiped out, many players lost a year of eligibility on their contracts. The young Ryan Kesler finally got to play his first full season with the Vancouver Canucks in 2005-06. Kesler didn't disappoint, recording 23 points in a limited role and showing great potential as a shutdown center. Kesler rejected a $564,000 qualifying offer from the Canucks, opting to become a RFA. It turned out to be a good decision for Kesler, as the Flyers gave him a one-year offer sheet worth $1.9 million. The Canucks decided to match the offer, so Kesler essentially nearly quadrupuled his salary by going to restriced free agency.

Kesler would remain with the Canucks for another eight years before being traded to Anaheim.

11 Milan Lucic Joining An Old Enemy

Kirby Lee-USA TODAY Sports

Milan Lucic was public enemy no.1 in Montreal, having spent many years with the archrival Boston Bruins. However the Bruins traded Lucic to Los Angeles a year before Lucic became a UFA. From that point on, Montreal fans began to wonder if the power forward would make his way to Montreal.

Reports emerged this past July 1st that the Canadiens had serious interest in Lucic and even offered him the most money. That's crazy to think, considering Lucic got a six year deal worth $42 million from the Edmonton Oilers. Lucic commented that the Canadiens trading for Shea Weber, while also having his friend Brendan Gallagher on the team, made the offer enticing, but he settled on the Oilers for a chance to play with Connor McDavid. You can't really blame him, can you?

10 Keith Tkacuk To Chicago

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As we later found out, Keith Tkachuk and Jeremy Roenick would eventually form a dynamic duo with the Coyotes, where they helped the franchise reach the playoffs several times in the late 90s. However, they almost teamed up earlier in Chicago.

Prior to the start of the 1995-96 season, it was common knowledge that the Winnipeg Jets would be relocating to Phoenix for the 1996-97 season and the team was in dire finanical staits. Sensing that, Tkachuk sought offers as a restricted free agent and he signed a five-year, $17 million offer sheet with the Chicago Blackhawks. In a surprising move, the Jets opted to match the offer, keeping Tkachuk in Winnipeg for the franchise's final season north of the border.

The Tkachuk/Roenick alliance happened a year later, as Roenick would be traded to the Coyotes just prior to their move to Phoenix.

9 Sergei Fedorov Nearly Gives Up Cups For Dollars

via themajors.net

When you're in a good situation in the NHL, it's never really a good idea to give that up. We've seen countless careers dwindle when a player leaves a great team to chase the almighty dollar, but that's what Sergei Fedorov almost did in the 1997-98 season. After the Red Wings finally captured a Stanley Cup in '97, Fedorov held out for the start of the next season, seeking a significant pay raise. He got one from the Carolina Hurricanes, who had just reloacted from Hartford.

Despite the team being a bottom feeder at the time, Fedorov agreed to an offer sheet worth $38 million over six years. Despite a heavy front-loaded bonus in the contract, the Wings matched the offer, as they were pursuing a repeat. The Wings signed Fedorov and they would repeat as Cup champions.

8 Teemu Selanne Nearly A Flame

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Teemu Selanne was drafted by the Jets in 1988, but due to the Jets' organizational philosophy of letting their European picks develop in their native countries, Selanne spent his first few pro eligible years in Finland. By 1991, the Jets began pursuing Selanne to get him over to Canada. The problem was that Selanne was a restricted free agent and a playoff contending Calgary Flames team offfered him an offer sheet of three years at $2.7 million. The contract was significant, as the Jets were offering him $1.5 million less.

Despite the risk of taking an unproven player at that rate with the Jets struggling financially, they bit the bullet and matched the offer. They would soon be rewarded with a 76-goal rookie season by Selanne.

7 Brett Hull To Montreal

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By the summer of 2001, it was apparent that the Dallas Stars' potential of a dynasty was coming to an end. Just two summers removed from his Cup winning goal in 1999, Brett Hull hit the open market and as expected, had no shortage of suitors.

Hull received just a two-year, $9 million offer from the Detroit Red Wings. He received superior offers from the New York Rangers, who were notorious for overspending on free agents pre lockout, but another team emerged with a more lucrative offer. After three years of missing the playoffs, the Montreal Canadiens tried to make a splash and offered Hull significantly more than the Red Wings. However, with the Wings being a serious Stanley Cup contender, Hull chose to go to Detroit and chase his second Stanley Cup ring, which he would win that very season.

6 Jagr To The Oilers

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Following his return to the NHL for the 2011-12 season, after three years of playing in the KHL, Jagr admitted that he almost signed with the Edmonton Oilers before leaving for Russia in 2008.

"When I got the offer from Edmonton I had already promised to go to Omsk,” said Jagr.

“You know how it is, you don’t want to break a promise…sometimes once you break something, it can hurt you later. It was only a matter of days, one or two, before I was going to be going to Russia. I thought I was too old to change (NHL) teams after playing for the Rangers and I told the Omsk organization if I didn’t go back to New York, I would sign in Russia.”

Back then, the Oilers weren't a rebuilding team. They were just a couple of years removed and landing Jagr eight years ago definitely would have provided a spark.

“I was interested. I talked to (then GM) Kevin Lowe. They had a new owner. They have a young, good team. It just didn’t happen,” said Jagr. “Maybe in my next life.”

5 Artemi Panarin To Montreal

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Artemi Panarin won last year's Calder Trophy as rookie of the year and recently signed a two year extension that will keep him in Chicago through the 2018-19 season. Part of why Panarin has been so successful since his crossover from the KHL has been that he's played with Patrick Kane. However, he was very close to playing in hockey's mecca.

Panarin's fellow Russians Sergei Gonchar and Andrei Markov even reached out to him, trying to get him to Montreal. With Panarin's team down 3-0 in a KHL playoff series, a visit to Montreal was scheduled by Panarin's agent, with it looking like Panarin's KHL season was about to end. However, Panarin's KHL club would come back in the series and ended up winning the league championship. That put everything on hold, allowing the Blackhawks to swoop in with an offer of their own.

4 Shea Weber To Philly

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Shea Weber is still on a massive contract that was signed back in the 2011-12 offseason. After the Nashville Predators had already lost Ryan Suter to free agency, they didn't want to lose their captain too. The Flyers were prepared to offer the house for Weber and with the stud defenceman as an RFA, the Flyers gave Weber a 14-year deal worth $110 million. We all know the FluerDespite the Predators being a team on a tight budget, they decided to retain their captain and try to compete for a Stanley Cup. Luckily, they eventually got a worthy defence partner for Weber in Roman Josi.

Weber would remain in Nashville for another four years, but was traded this past offseason to Montreal for P.K. Subban. Weber remains on the Habs' books through the 2025-26 season.

3 Joe Sakic Signs Offer Sheet With Rangers

via thestar.com

Joe Sakic played his entire career with the Quebec Nordiques/Colorado Avalanche franchise. He's even the President of Hockey Operations for the Avs today, so it's really hard to picture him being anywhere else. However that was almost the case following the 1996-97 season. After already having Wayne Gretzky on the books from the season before, the Rangers tried to make another big splash in landing one of the best centers in the game. With Sakic being an RFA, the Rangers signed Sakic to an offer sheet of three years worth $21 million. The Avs knew Sakic was their lifeline and even if the money was more than they wanted to spend, they matched the offer.

The pay raise for Sakic would soon trigger a pay increase around the league, as this deal set a new standard for star centers.

2 Mr. Hockey Goes To Broadway

via sportsnet.ca

Gordie Howe was everything to the game of hockey for so long. While he played many years in the WHA, his time with the Detroit Red Wings is what we remember him for the most. However, had another organization been a little more patient, we'd be writing a whole new story today.

Back when Gordie Howe was a 15-year-old kid, he received an invite to the New York Rangers' training camp. Scout Fred McCorry had seen Howe play in Saskatoon and convinced the Rangers the kid was worth a shot.

In the end, New York proved to be too intimidating for Howe, who was a shy, introverted kid. Howe did not like the big city at all, which affected his performance in camp. As a result, the team's veterans were teasing him and Howe got homesick. The Rangers eventually sent Howe home, which opened the door for another team to swoop in.

Fred Pinckney, a Red Wings scout, gave Howe a call and convinced him to go to the Red Wings' camp in Windsor, Ontario. The rest is history.

1 The Great One Returns To Canada

via sportsnet.ca

After a disappointing tenure in St. Louis, Wayne Gretzky was ready to test the free agent market. With Pat Quinn as the head coach and general manager of the team, they had a great figurehead to pursue Gretzky.

"The Canucks had (Gretzky) signed at night verbally, and he (told Quinn), ‘Look. I’ll sign the papers formally in the morning," Sportsnet’s Elliotte Friedman told Sportsnet 590.

Signing Gretzky would have been huge not only for the Canucks, but for the whole country of Canada, as the whole country felt the affect of Gretzky being traded back in 1988.

Friedman continued to explain how everything unraveled just when it looked like Gretzky would be a Canuck. Orca Bay CEO Stan McCammon heard about the impending deal and called Quinn, ordering, ‘We want this done tonight.’

"Quinn told McCammon that Gretzky was committed and not to worry."

"No, no, no. We're doing this tonight. I want it formalized. No questions," McCammon instructed Quinn.

After getting the order from his owner, Quinn called Gretzky, asking him to sign the papers write away.

Gretzky replied with: "I told you I'd sign them the morning."

"Nope," Quinn said. "I need to have it tonight."

And just like that, Gretzky got a bad vibe with the Canucks and the deal was off. He would eventually sign with the New York Rangers, reuniting with his old Oiler teammate Mark Messier.

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