The 25 Most Curious NHL Free-Agent Decisions of All Time

Tom Urtz Jr.Contributor IJanuary 16, 2013

The 25 Most Curious NHL Free-Agent Decisions of All Time

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    The NHL's free-agency period is always an interesting time of the year, and throughout the history of free agency, there have been many curious decisions.

    These decisions include non-moves, curious low-ball offers, over-payments of players like Bobby Holik and even teams passing over a young prospect free agent named Gordie Howe.

    A lot of times, free-agency moves are understood in hindsight, but that doesn't make certain moves less curious.

    Free agency really started to boom in the 1990s and 2000s, as it was less common in previous decades, where trades were more prevalent. Additionally, there is not much salary information available from past decades.

    With so many transactions that have taken place throughout the history of free agency, here are 25 of the most curious free-agent decisions of all time.

New York Rangers Pass over Gordie Howe

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    Gordie Howe was one of the greatest wingers in the history of the NHL, and he is a player who is iconic with the Detroit Red Wings.

    However, the New York Rangers were one of the first professional teams to discover this "free agent," but after inviting him to a training camp in 1943, they failed to sign the prospect because of his inability to adjust to the speed of the game.

    In 1944, Howe was invited to the Detroit Red Wings' camp, and he went on to have a prolific NHL career.

    This is a curious decision in hindsight that leaves you wondering, what if?

Bobby Hull Signs with the WHA for $1 Million

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    When it was rumored that the KHL was preparing a small fortune to keep Ilya Kovalchuk overseas, comparisons where immediately made to Bobby Hull and the Winnipeg Jets' infamous $1 million bounty offer.

    Hull was the Chicago Blackhawks' top sniper, and he had the league's hardest shot. However, he was vastly underpaid for his contributions to the team, so the Jets of the World Hockey Association signed him to a 10-year deal worth $1 million.

    This deal made the WHA a legitimate league, and it isn't curious that Hull "took the money and ran," but rather that Chicago didn't put up a bigger fight to retain its top superstar.

New York Islanders Let Bryan Trottier Walk

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    Bryan Trottier was one of the New York Islanders' greatest players during the 1980s, and he was a crucial contributor who was also a great leader.

    However, management decided to release Trottier from his contract after his offensive numbers declined. His offense may have been on the decline, but Trottier was a player who still had some value.

    The Hall of Fame forward went on to win back-to-back Stanley Cups with the Pittsburgh Penguins, where he served in an important role with the team as a veteran leader.

St. Louis Blues Present Offer Sheet to Brendan Shanahan

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    When the St. Louis Blues presented an offer sheet to Brendan Shanahan, it was one of the most curious moves in the history of offer sheets, and it was a move that really cost the team.

    In 1990, the Blues successfully offer sheeted Scott Stevens from the Washington Capitals, and the compensation was five first-round draft picks.

    The next year, they offer sheeted Shanahan and attempted to compensate the Devils with a package highlighted by Curtis Joseph. An arbitrator ultimately ruled that the compensation would be Scott Stevens, and it was a very interesting decision.

    In the end, the move to acquire Brendan Shanahan was ultimately five draft picks and Stevens, who became a future franchise defender for New Jersey.

    Had the Blues not went through with this move and kept Stevens, the team's fate could have been drastically different.

New York Rangers Sign Guy Lafleur After 4-Year Break from NHL

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    Guy Lafleur was one of the greatest players in the history of the NHL, and the New York Rangers made the curious decision to sign the "free agent" after he impressed in an exhibition game that GM Phil Esposito attended.

    The former Canadiens great impressed in the limited action he saw in New York, as he scored 18 goals and 45 points in 67 games played.

    This move was curious at the time considering how Lafleur had left the NHL, but the one-year deal really paid off for the Rangers.

New York Rangers Sign Bobby Holik

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    Throughout his NHL career, Bobby Holik was the subject of many curious free-agent signings.

    The first free-agent signing with the New York Rangers was very curious, and the book Money Players by Bruce Dowbiggin did a great job breaking down the negotiations on Canada Day with current Canucks GM (former agent) Mike Gillis.

    Holik had turned down an offer from the New Jersey Devils that was fair market value, but the Rangers raised the ante to a contract that paid Holik $9 million a season.

    The experiment never panned out for the Blueshirts, and it was one of the most curious free-agent decisions of Glen Sather.

Joe Sakic Signs the New York Rangers' Offer Sheet

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    In many ways, the New York Rangers' offer sheet with Joe Sakic was a catalyst for the increase of salaries for star players in the NHL.

    The Rangers made a curious and bold move by signing Sakic to a three-year deal worth $21 million, and it was very curious that the Avalanche captain signed it.

    Sakic was an established star player, a respected leader and a player who just captained the team to a Stanley Cup title, so it was curious that the star was looking to jump ship. However, the Avs were eventually able to match the offer and retain Sakic.

Toronto Maple Leafs Splurge on Jeff Finger

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    After one decent season with the Colorado Avalanche, the Toronto Maple Leafs splurged to sign defender Jeff Finger to a four-year deal worth $4.5 million a season.

    After Finger failed to live up to expectations, he was sent to the AHL, where his salary did not count against the cap until his contract expired.

Curtis Joseph Is Not Retained by the Toronto Maple Leafs

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    When you look at the state of the Toronto Maple Leafs' goaltending situation over the past few years, this move really stings when you consider how good Curtis Joseph was.

    Bruce Dowbiggin's Money Players provides an intriguing perspective on when Curtis Joseph became a free agent in July of 2002. After Joseph was handed a "low-ball" offer, he decided to test the market. Management was not thrilled.

    There is some speculation that there was some bad blood between Pat Quinn and Cujo that stemmed from his benching during the Salt Lake City Olympics, but both never admitted to the rumors.

    Joseph ultimately signed with Detroit after Toronto turned its back on one of its most successful goaltenders, and it is a move that still stings today.

Wade Redden Gets a King's Ransom

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    Wade Redden struggled during the last two years of his contract with the Ottawa Senators, yet Glen Sather made the head-scratching decision to sign Redden to a contract with the same A.A.V. of $6.5 million.

    Redden did nothing to prove he should maintain his salary, and Sather gave him a five-year-deal to boot.

    Luckily, with an anticipated buyout approaching, Sather's biggest mistake to date as Rangers GM will be undone.

Ville Leino Receives a Massive Contract After One Year

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    Although Ville Leino's payday occurred recently, it still remains one of the most curious decisions in the history of free agency.

    After one skilled season in which Leino scored 53 points with the Philadelphia Flyers, Leino was signed to a six-year, $27 million contract with the Buffalo Sabres on the first day of free agency.

    This currently stands as one of the most curious decisions of all time because he was given such a hefty contract with only 30 career NHL goals.

Pittsburgh Penguins Don't Lock Up Ron Francis

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    Ron Francis' career was one of the greatest in the history of the NHL, and he was a player who won multiple Stanley Cups.

    After being traded to Pittsburgh from the Hartford Whalers during the 1990-91 season, Francis went on to win back-to-back Cups with the Penguins.

    After many successful seasons with the Pens, they did not re-sign him, and Francis returned to the newly relocated Carolina Hurricanes.

    After many amazing seasons with the Pens, it is surprising that Pittsburgh didn't try harder to retain its star forward and captain.

Dallas Stars Decide to Let Brett Hull Walk

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    Brett Hull was one of the NHL's most lethal goal scorers, and he was a highly coveted forward throughout his career.

    After going to the Stanley Cup Final in two consecutive years with the Dallas Stars and having an amazing point-per-game year in the last year of his contract, the Stars declined to exercise a club option for the following season.

    This was a very curious and confusing move because Hull was still one of the league's most lethal goal scorers, and he was worth $7 million a year.

    This move ultimately came back to bite the team when Hull went to a conference rival in the Detroit Red Wings. There, he won a Stanley Cup and was the NHL's top playoff goal scorer all in the same year.

Detroit Fails to Re-Sign Sergei Fedorov

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    Sergei Fedorov was one of the most talented two-way offensive forwards in the history of the NHL, and he was a dynamic playmaker who was an amazing player for the Detroit Red Wings.

    He was a fixture in the Wings lineup, so it was curious when the team failed to re-sign its talented center.

    He ultimately signed with the Anaheim Ducks, but he didn't spend much time with the team because of the lockout, and he proceeded to bounce around a few teams throughout the rest of the league.

    Had Fedorov stayed in Detroit, he may have had more success late in his career.

Ottawa Senators Choose to Sign Wade Redden over Zdeno Chara

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    At the end of the 2005-06 season, the NHL's first season with a salary cap, the Ottawa Senators were in a financial bind: They had to make a choice to re-sign either Wade Redden or Zdeno Chara.

    The Senators ultimately made the curious choice of deciding to ink Redden to a deal worth $6.5 million a season, and Chara signed with the Boston Bruins for a deal that paid him $7.5 million.

    Chara was the team's better defender, yet the Sens decided to go with Redden, who ultimately regressed as a defenseman.

Shea Weber's Offer-Sheet Situation

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    The Nashville Predators matched Shea Weber's offer sheet signed by the Philadelphia Flyers this summer, and the structure of the offer sheet is one of the most brutal ever constructed.

    Weber is to be paid $27 million a year ($14 million salary, $13 million signing bonus) for the next four years.

    Although the cap hit of $7,857,143 a year is manageable, Nashville put themselves in a huge financial bind by matching it. The structure of the offer sheet is one of the most curious ever constructed in league history.

WHA's Philadelphia Blazers Poach Derek Sanderson, Proceed to Buy out Contract

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    The World Hockey Association made headlines when it poached Bobby Hull from the NHL, but it also signed Derek Sanderson, a center from the Boston Bruins, to a contract worth $2.6 million to play for the Philadelphia Blazers.

    This deal, according to Wikipedia, made him the highest-paid athlete in the entire sporting world at the time. However, the signing did not pay off and the team paid Sanderson $1 million upfront to go back to the NHL.

    This move was strange because the WHA didn't even give its investment a chance before blowing up the experiment.

New York Islanders and Rick Dipietro

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    After eight wins over the course of only four seasons, the New York Islanders signed Rick DiPietro to a 15-year contract worth $67.5 million.

    Considering the young goalie had not proven himself, the move was curious because he was not a player in high demand.

    This move is often considered one of the worst of all time, and fans are curious to know what was going through Charles Wang's head when he authorized this deal.

Buffalo Sabres Decide Not to Negotiate During Season, Lose Drury and Briere

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    The Buffalo Sabres had a long-standing policy of not negotiating with free agents during the regular season, and it was something that almost cost them all three of their top players. Thomas Vanek was offer sheeted by the Edmonton Oilers, but Buffalo matched the offer sheet.

    However, the unwillingness to negotiate during the regular season with co-captains Chris Drury and Daniel Briere led to the star players' departure from Buffalo.

    This situation was very curious because teams are supposed to do everything possible to retain top-end talent.

St. Louis Blues Decide Not to Give Brett Hull a No-Trade Clause

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    Brett Hull makes a second appearance on the list because his former team made a curious decision when it came time to lock up the superstar sniper.

    When Hull's contract was up with the Blues, he wanted a deal with a no-trade clause because he wanted some security.

    When the team would not budge, he left as a UFA and he signed with the Dallas Stars, with a contract that added $2 million and the NTC that Hull wanted.

    The "Golden Brett" went on to have an amazing time in Dallas, where he won his first career Stanley Cup.

Glen Sather Overpays Scott Gomez

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    Glen Sather has been able to undo almost every bad contract handed out since the beginning of the salary-cap era. One of his most curious moves was signing Scott Gomez to a massive contract after landing top-six center Chris Drury during free agency.

    Gomez was a center who scored 50 to 60 points a year on average, but on the first day of free agency in July of 2007, Gomez signed a $51.5 million, seven-year contract with the New York Rangers.

    Although he was talented, it was a curious move that Sather felt the need to overpay Gomez by signing him to a deal that paid him $7,357,143 a season.

Alexei 'Ca$hin' Yashin

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    Alexei Yashin was a player who liked to try and renegotiate deals after signing them year after year, and he earned the nickname of Alexei "Cashin" Yashin.

    The Ottawa Senators eventually got fed up with him, and they dealt him as a free agent to the New York islanders, where Mike Milbury made the curious and very stupid mistake of rewarding the ungrateful Yashin with a 10-year contract for $87.5 million.

    The experiment was unsuccessful, as Yashin was bought out in 2007.

Denis Savard Signs with the Tampa Bay Lightning

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    Denis Savard was one of the greatest scorers in the history of the Chicago Blackhawks, and he surpassed the 100-point plateau five times throughout his career. Savard was a talented player who had a brilliant career, yet he made a curious decision toward the end of his career.

    The former superstar had regressed in points in the early 1990s, but he was still a solid bottom-six player.

    When he became a free agent, Savard signed with the upstart Tampa Bay Lightning franchise. It was a surprising move considering the caliber of Savard as a player.

New York Rangers Choose Not to Re-Sign Mark Messier

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    In 1997, Mark Messier wanted to re-sign with the New York Rangers so he could finish his career with the franchise he led to its first Stanley Cup in 54 years.

    However, management felt that Messier wasn't worth the contract, and he was released to free agency.

    He eventually signed with the Vancouver Canucks, and the combination of New York's unwillingness to re-sign Messier and his tenure in Vancouver made this a curious transaction.

New Jersey Devils Fail to Re-Sign Bernie Nicholls

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    Bernie Nicholls is a forward who could be Hall of Fame-bound in a few years, and he was a player who bounced around the NHL.

    Late in his career, Nicholls was traded to the New Jersey Devils, where he changed his game under Jacques Lemaire. However, the team did not re-sign him after the 1993-94 season in which Nicholls had 13 points in 16 playoff games.

    Nicholls then went to the Chicago Blackhawks, where he had two potent offensive years in which he had two shortened seasons. It was a curious move that the Devils were unable to re-sign their valuable veteran.