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Best NHL Free Agent Signings Ever – Ranking the Top 10 – Gambling Sites

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Free agency is an important aspect of any sport, and the NHL is no different. Teams would love to build their roster through the draft, but free agency is the best place to land a proven talent.
You’ll not often see a big contract pan out, but we’ve seen exceptions. Sometimes, it’s a match made in heaven for a player and team. That leads to the best NHL free agent signings.
No one could’ve imagined these players outperforming their expectations. Here are the ten of the greatest NHL free agent signings we have seen.
Following a successful three-year tenure with the Chicago Blackhawks, 37-year-old Brett Hull signed a two-year, $9 million deal with the Detroit Red Wings. Detroit entered the season looking to win their third Stanley Cup in seven years.
The Red Wings had a roster full of future Hall of Famers, including Hull. He recorded 30 goals, 33 assists, and 63 points in the regular season. Detroit finished with the best record in the league, winning the Stanley Cup.
The 2002-03 season marked his best with Detroit. Hull had 37 goals, 39 assists, and 76 points. Only once in his previous five seasons did he clear 75 points.
On this day in 2001, the @DetroitRedWings signed Brett Hull #Hockey365 #LGRW
Detroit opted to give him a one-year, $5 million extension for the 2003-04 season. The Red Wings had another great season, winning the President’s Trophy with 109 points. Hull’s scoring decreased, but his 43 assists were the most in his Red Wings tenure.
Unfortunately, the Red Wings lost in the Conference Finals. This marked the end of Hull’s tenure with Detroit.
The Red Wings already had a successful roster before bringing Hull into the fold. However, he stands out as one of the biggest NHL free- agent signings because of his impact on the Stanley Cup winning team.
The Detroit Red Wings were a powerhouse through the 1990s and 2000s. Brett Hull played a significant role in the early 2000s, but Brian Rafalski was the critical free agent signing in the late 2000s.
Rafalski had a successful seven-year career with the New Jersey Devils, but he opted to sign a five-year, $30 million deal with his hometown Detroit Red Wings in 2007. Detroit was coming off a Conference Finals loss in 2006.
The defenseman never had more than nine goals with the Devils. Rafalski scored 13 and 10 goals in his first two seasons with Detroit. He left his mark as one of the best NHL free agency signings after helping the Red Wings win the 2008 Stanley Cup.
Related: Best NFL Free Agent Signings Ever
Detroit nearly went back-to-back, losing seven games in the 2009 Stanley Cup Final. Rafalski recorded three goals and nine assists in the series.
He missed 18 games in the 2010-11 season, but his 0.76 points per game tied the highest mark of his career. Rafalski didn’t play the final season of his contract, retiring after the season.
Despite being in his upper 30s, his Red Wings tenure marked the best stretch of his career.
Nowadays, we remember Martin St. Louis for his legendary career with the Tampa Bay Lightning. However, people may not know he started his career with the Calgary Flames.
St. Louis had a small role, prompting him to sign a two-year deal for a mere $540K. He had a pair of solid seasons, recording 75 points over the two seasons. Tampa Bay gave him a two-year extension.
We saw him blossom into a star for the 2003-04 season. St. Louis won the Hart Trophy after leading the NHL with 56 assists and 94 points. Did I forget to mention he led the Lightning to a Stanley Cup title?

Martin St. Louis, a 25-year-old free agent, signs with the @TBLightning. He wins the Hart Trophy, the Art Ross Trophy and Ted Lindsay Award in 2003-04, when he helps the #GoBolts win the Stanley Cup for the first time in their history.
Following the lockout, Tampa Bay gave St. Louis a six-year, $31.5 million extension. That’s not bad for a player who started on a contract under 600K. He certainly left his mark as one of the biggest free agent additions in NHL history.
St. Louis spent eight more seasons with the Lightning, making the All-Star Game four times. At 37 years old, he led the NHL with 43 assists and 60 goals in a 48-game shortened season.
An undrafted player that signed for 540K in 2000. Not bad for a Hockey Hall of Famer.
You can argue that Marian Hossa’s one-year deal with the Detroit Red Wings in 2008 could be one of the biggest NHL free agency moves. However, there’s no denying his contract with the Chicago Blackhawks.
Hossa played for four teams before signing a 12-year, $62.8 million contract with the Blackhawks in 2009. It didn’t take long for people to wager on the Blackhawks with the best sports betting sites to make a profit.
Hossa reached the Stanley Cup for the third straight season with a different team. This time, he helped the Blackhawks win the Stanley Cup. They replicated this feat twice in the next five years.
On this day in 2009, the #Blackhawks landed the best free-agent signing in Chicago history. Future first-ballot Hall of Famer & three-time Stanley Cup champion Marian Hossa. There’s nothing I found more hilarious than Big Hoss pulling out the clap-bomb on a breakaway for a goal😂
Hossa missed 15+ games in his first two seasons with Chicago, but he made the All-Star team in 2012. That marked his best season with the Blackhawks, recording 29 goals, 48 assists, and 77 points.
He continued to be a consistent goal scorer throughout his Blackhawks tenure. Hossa recorded 20+ goals in six of his eight seasons in Chicago.
Despite not playing out the 12-year contract, Hossa going to the Blackhawks is one of the best NHL free agent signings. He was the missing piece to the Blackhawks’ Stanley Cup runs.
Brett Hull makes another appearance? Before enjoying a successful tenure with the Detroit Red Wings, Hull left his mark with the Dallas Stars. He signed a three-year, $17 million deal in 1998.
Dallas lost in the 1998 Conference Finals, but Hull looked to lead them to the Stanley Cup Final. He missed 21 games, but the Stars claimed the President’s Trophy with 114 points.
The Stars won the 1999 Stanley Cup behind Hull’s game-winning goal in Game 6. However, there was much controversy about the goal. Nonetheless, it gave the Stars their first Stanley Cup in franchise history.
The 2000-01 season marked the best season of his Dallas tenure as you can see with these numbers.
He struggled the season before, but Dallas still made the Stanley Cup Final. They lost to the New Jersey Devils in six games.
Hull’s tenure with the Stars only lasted three seasons, but back-to-back Stanley Cup Final appearances will earn you a spot among the biggest NHL free agent signings. The Stars cleared 100 points in his three seasons with the team.
The only bad thing about this contract was Dallas didn’t re-sign him. We know what he did with the Red Wings.
We can’t give Brett Hull all the credit for the Dallas Stars run through the late 1990s. Goalie Ed Belfour played a significant role in Dallas’ success. He signed a three-year, $10 million contract following a successful tenure with the Chicago Blackhawks.
His play slipped in the 1996-97 season, but he returned to form with the Stars. Dallas went from 66 to 104 points in his first season. Belfour kicked off his Dallas tenure by leading the NHL with a 1.88 GAA.
We know the Stars claimed the 1999 Stanley Cup Finals. Check out the regular season numbers from Belfour.
That was enough validation for Dallas to make one of the best NHL free agency moves of all time. Dallas failed to repeat as champions, but we can’t blame it on Belfour. He led the league with a .919 save percentage while recording a 2.10 GAA.
Belfour’s numbers slipped in his final two seasons with the Stars, but he remained a serviceable player. He certainly played a crucial role in Dallas’ Stanley Cup title.
You almost wonder why the Blackhawks or San Jose Sharks let him go. He had great numbers in the early 1990s.
Scott Niedermayer had a tremendous 13-year career with the New Jersey Devils, but he wanted to play with his brother with the Anaheim Ducks. That led to him taking less money and signing a four-year, $27 million contract.
Anaheim succeeded ahead of Niedermayer’s tenure, losing to his Devils in the 2003 Stanley Cup Final. He cleared 60 points in his first two seasons with the Ducks. Everything came together in the 2007 playoffs.
The Ducks won their first Stanley Cup in franchise history in 2007, with Niedermayer winning the Conn Smythe Award.
Niedermayer contemplated retirement but rejoined the Ducks for the 2007-08 season. He made his first of back-to-back All-Star Game appearances. Niedermayer retired following the 2009-10 season.
Anaheim only won one playoff series in the final three seasons of his contract. However, he made a monumental impact in his first two seasons. The Ducks don’t win the 2007 Stanley Cup without Niedermayer.
In turn, we recognize this as one of the biggest free agent signings in NHL history. The Ducks had one of the greatest defenseman duos ever with Niedermayer and Chris Pronger.
Adam Graves was a Stanley Cup champion with the Edmonton Oilers, but he didn’t significantly impact their championship. That prompted him to sign a five-year, $2.44 million deal with the New York Rangers.
New York was a consistent playoff contender before Graves, but they couldn’t take the next step. Graves played a crucial role in New York becoming a Stanley Cup contender.
He recorded 55+ points in his first two seasons. The 1993-94 season marked the best of his career. Graves set career highs with 52 goals and 79 points. He led the Rangers to their first Stanley Cup title since 1940.
on this day in 1991, Adam Graves became a Ranger.
New York made the playoffs in the following three seasons but couldn’t make it back to the Stanley Cup Final.
Graves made his biggest impact in the early portion of his contract, but he produced a pair of 30+ goal seasons in the late 1990s. He remained with the Rangers through 2001 before spending the final two years of his career with the San Jose Sharks.
His impact went beyond the hockey rink. Graves won the King Clancy Memorial Trophy and Bill Masterton Memorial Trophy for his perseverance and leadership. It gives me shades of the top MLB free agent signings, which you take a look for yourself below.
MLB free agency gives teams a chance to land an impact player. Without a salary cap, bigger market teams can shoot for the stars with their signings. These free agents proved that no amount of money was enough to justify their success. They exceeded their…
The majority of the biggest NHL free agency moves came in the 1990s and early 2000s. Zdeno Chara signing with the Boston Bruins should be more relatable to the current generation.
Chara was an eight-year veteran when he signed a five-year, $37.5 million contract with the Bruins. The 6’9” defenseman changed the outlook of their franchise for the next decade.
If you don’t want a long explanation for Chara being one of the best NHL free agent signings, just know that he made the All-Star Game in four of his first five seasons with the Bruins. He recorded between 43 and 51 points in those five seasons.
16 years ago today, the #NHLBruins organization forever changed with the signing of free agent defenseman Zdeno Chara.
There hasn’t been a free agent signing in the NHL that has had the impact that Chara had on the Boston Bruins ever since that day in July 1st, 2006
It wouldn’t be a great free agent signing without a player winning the Stanley Cup. Boston came close a few times, but they closed the deal by defeating the Vancouver Canucks in the 2011 Stanley Cup Final.
That was the end of his contract, but he was far from done with Boston. Chara spent nine more seasons with the Bruins. They didn’t return to the Stanley Cup Final, but Chara continued to produce as a top defenseman.
His 14-year tenure with Boston included a Stanley Cup, Norris Trophy, and five All-Star Game appearances.
The best NHL free agent signing ever belongs to the New Jersey Devils acquiring Scott Stevens.
This was a unique scenario because the Devils didn’t sign Stevens outright. They acquired him as compensation for the St. Louis Blues acquiring Brendan Shanahan from the Devils.
Stevens was a three-time All-Star in his first nine seasons, but his game elevated to another level in New Jersey.
The 1994-95 season was the only time in the 1990s Stevens didn’t make the All-Star Game with New Jersey. He recorded 55+ points in 1992 and 1993, but 1994 marked his best NHL season.
Those are impressive numbers for anyone, nonetheless a defenseman. The following season, he helped the Devils win their first Stanley Cup.
After winning one playoff series from 1996 to 1999, New Jersey had an unprecedented run in the early 2000s. They made the Stanley Cup Final in 2000, 2001, and 2003. New Jersey won the title in 2000 and 2003, with Stevens winning the Conn Smythe Award in 2000.
He remained with the Devils for 13 seasons. Stevens retired in 2004, making the Hall of Fame three years later.
NHL free agency is a crucial time for teams. It’s a great chance to send your franchise in the right direction. We’ve seen how the best NHL free agent signings impacted their team.
This sets off a domino effect for the league. It helps that particular team’s Stanley Cup odds while decreasing others. It’s a friendly reminder that betting is about more than individual games.
Bettors have the opportunity to wager on players signing with a team in free agency. They can do so by visiting the best hockey betting websites.
Nicholas has been a Sports Writer with since May 2021. He has a rich sports background, writing about NASCAR, NFL, NBA, MLB, NHL, Golf, etc. Nick is always ready for a new challenge.
He enjoys rooting on D.C. sports teams, including the Commanders, Wizards, and Capitals.

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