New York Rangers’ worst free-agent signings in history: Wade Redden leads the pack
By John Kreiser,
2024-08-23
An albatross is more than just a bird. In hockey lingo, it’s the kind of free agent signing you don’t want your team to end up with.
The New York Rangers have never been reluctant to spend big money on free agents. But being willing to open your wallet is one thing; opening it for the right player at the right time is a whole different issue. While they’ve had some big hits over the years, the Rangers have also inked a sprinkling of albatross contracts that have set the organization back — sometimes immensely, especially in the salary cap era. Here’s a look at the 10 worst free-agent signings in Rangers history:
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10. Richards Got Rich
The Signing: Rangers signed center Brad Richards to a nine-year contract
Date: July 1, 2011
Why it mattered: The Rangers have never been open their wallet for free agents. Richards, the biggest fish in the 2011 free agent pool, had won the Conn Smythe Trophy as playoff MVP in 2004, when John Tortorella led the Tampa Bay Lightning to the Stanley Cup. With Tortorella now in charge of the Rangers, it was no surprise that the 31-year-old center wound up signing a front-loaded mega-deal that brought him to New York.
Richards was one of the NHL’s top playmakers and was coming off seasons of 91 and 77 points with the Dallas Stars. He had lost a step and didn’t come close to those numbers in New York, but his 66 points in 2011-12 helped the Rangers finish first in the Eastern Conference, and he was a 20-goal scorer two years later when the Rangers got to the Stanley Cup Final for the first time since winning it in 1994.
However, the collective bargaining agreement that ended the 2012 lockout turned Richards’ contract into a liability. The deal had been structured so that he wouldn’t play the last three seasons (but would earn $1 million per season). However, such contracts were considered cap circumvention under the new CBA, meaning that if he retired early, the Rangers would be on the hook for more than $5 million for each of those three seasons — for a player no longer on the roster. They wound up buying out the final six seasons of the contract, meaning that Richards ended up getting paid about $53 million for his three seasons in New York.
He signed with the Chicago Blackhawks and almost wound up facing his old team in the 2015 Final, but the Tampa Bay Lightning knocked off the Rangers in Game 7 to win the Eastern Conference Final before losing to the Hawks in six games.
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9. Cracked Glass
The Signing: Rangers sign forward Tanner Glass to a three-year contract
Date: July 1, 2014
Why it mattered: Every new coach wants to put his own stamp on his new team. Alain Vigneault was no exception.
Vigneault liked Glass, a forward who contributed grit but little else, from his days coaching the Vancouver Canucks. He reportedly pushed to sign Glass after being named coach of the Rangers in April 2014, and GM Glen Sather inked him to a three-year contract on the first day of free agency.
Glass would stand up for his teammates and was among the most popular players in the locker room. But he contributed almost nothing offensively, was a black hole when it came to puck possession and never came close to being worth the average of $1.45 million the Rangers were paying him.
He contributed one goal, six points and 98 penalty minutes in 66 regular-season games in 2014-15, and one assist while playing all 19 games in the Stanley Cup Playoffs — including the Game 7 loss to the Lightning that prevented them from returning to the Final.
But as the game became faster, Glass was increasingly a player out of his era. He was waived early in 2015-16 and spent most of the final two seasons of his contract in the NHL.
Glass gave it all he had on every shift. But with the NHL in a state of flux, that wasn’t enough.
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8. Not Keen on Keane
The Signing: Rangers sign forward Mike Keane to a four-year contract
Date: July 7, 1997
Why it mattered: The Rangers spent much of the late 1990s chasing another Stanley Cup to go along with the one they won in 1994. They got to the conference finals in 1996-97 before being eliminated by the Philadelphia Flyers, and management was confident there was still a championship nucleus on hand.
GM Neil Smith wanted some additional veteran presence as an insurance policy against the potential loss of captain Mark Messier (who ultimately left for the Vancouver Canucks as a free agent), so he brought in Keane, a free agent who had won championships with the Montreal Canadiens (where he’d been captain) and Colorado Avalanche. The 30-year-old didn’t come cheaply — the four-year contract carried an average annual value of $2 million, a huge outlay for someone who didn’t play top-six minutes and had never scored more than 16 goals in a season.
But as was often the case in the 1990s and 2000s, the signing turned into a disaster. Keane and another veteran forward, Brian Skrudland (who signed the same day), formed two-thirds of an incredibly expensive third line that contributed little, offensively or defensively. For many Rangers fans, the most memorable happening involving Keane came when he inadvertently crashed into linemate Pat LaFontaine during a late-season game; the resulting concussion ended LaFontaine’s career.
With his team’s playoff hopes dimming as the trade deadline neared, Smith sent both players to the Dallas Stars as part of a late March housecleaning that brought in veteran forward Bob Errey and youngster Todd Harvey. Keane became a three-time champion with the Stars in 1999, played in the NHL until 2003-04 and spent five more seasons in the AHL. His time with the Rangers turned out to be a blip in one of hockey’s longest careers.
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7. Local Boy Doesn’t Make Good
The Signing: Rangers signed defenseman Kevin Shattenkirk to a four-year contract
Date: July 1, 2017
Why it mattered: The Rangers didn’t have to look far when seeking an offensive defenseman in the summer of 2017. Shattenkirk was a Rangers fan who grew up in New Rochelle, New York, about a half-hour from Madison Square Garden, and reportedly passed up bigger offers to sign a four-year deal worth an average of $6.65 million.
The contract didn’t seem to be out of line — in fact, he said he might have left money on the table but that this was his chance “to fulfill a lifetime dream.” Shattenkirk was the highest scorer of any free agent available in 2017 (56 points, a career-high) and had finished with at least 42 points in each of the five previous non-lockout seasons.
But things quickly went south. Shattenkirk’s offensive numbers tanked during an injury-filled first season, and the Rangers’ objectives changed as they fell out of the playoff race; they dealt away veterans like Ryan McDonagh and J.T. Miller while opting to rebuild. Management decided in the summer of 2019 that Shattenkirk didn’t fit into their future plans and opted to buy out the final two seasons.
The Tampa Bay Lightning quickly snapped up Shattenkirk, who helped them win the Stanley Cup in 2020. He then played three seasons with the Anaheim Ducks before joining the Boston Bruins in 2023-24.
Shattenkirk’s time with his hometown team can be filed under the heading of “be careful what you ask for.” In this case, neither side got what it was hoping for.
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6. Kaspar the Unfriendly Ghost
The Signing: Rangers sign defenseman Darius Kasparaitis to a six-year contract
Date: July 2, 2002
Why it mattered: The Rangers, who had missed the playoffs for five consecutive seasons, wanted a more physical presence on the blue line and outbid the Toronto Maple Leafs for Kasparaitis, who got a six-year deal worth an average of $4.25 million despite having never scoring more than four goals or 21 points in a season and having been hampered by a couple of major injuries.
Ironically, one of the callers in the recruiting drive for “Kaspar” was Rangers center Eric Lindros, who had missed a month after being knocked unconscious by a Kasparaitis check four years earlier while playing for the Philadelphia Flyers.
The Rangers paid Kasparaitis to be what he was at his best — a human wrecking ball who had no compunctions about leveling the NHL’s top players (he was famous for flattening both Wayne Gretzky and Mario Lemieux) with the kind of hip check that was rarely seen anymore. And he did just that in his first season with a rebuilding team, banging bodies and forcing opponents to keep an eye out for them.
But his hitting ability was often negated by his lack of speed and offensive skills. His playing style also led to more injuries, which slowed him even more. The Rangers waived Kasparaitis prior to 2006-07, making him a very expensive AHL defenseman for the final two seasons of his contract after he went unclaimed.
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5. Drury Disappoints
The Signing: Rangers signed center Chris Drury to a five-year contract
Date: July 1, 2007
Why it mattered: Drury won the Calder Trophy as the NHL’s top rookie in 1998-99, helped the Colorado Avalanche win the Stanley Cup two years later and was coming off back-to-back 30-goal seasons with the Buffalo Sabres in the summer of 2007 when Sather lured the 31-year-old center to the team he grew up watching as a boy in Connecticut with a five-year contract worth more than $7 million a year.
No. 1 center Michael Nylander had left for Washington, so coach Tom Renney installed Drury on the first line with Jaromir Jagr and Martin Straka on his wings. But while Drury was getting paid top-line money, he’d never been a first-line talent. That didn’t change with his new team: Drury’s offensive totals dropped off — and so did Jagr’s, who had put up 123 and 96 points in the previous two seasons but managed just 71 while largely playing with Drury and left for the KHL the following season.
Drury’s offensive numbers continued to drop. By 2010-11, injuries limited him to 24 games and one goal; the Rangers bought out the remaining year of his contract in July 2011. He was among the host of free-agent disappointments that riddled the Rangers in the first few years after the lockout that wiped out the 2004-05 season.
But unlike the others on this list, Drury’s time with the Rangers had a second act. He rejoined the team as director of player development in 2015 and was named president and general manager in 2021. He’s now trying to do as an executive what he couldn’t as a player — lead the Rangers to a championship.
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4. One Devil Disaster
The Signing: Rangers signed center Scott Gomez to a seven-year contract
Date: July 1, 2007
Why it mattered: The Rangers thought they had accomplished two things when they landed Gomez, a 28-year-old two-time Stanley Cup winner with the New Jersey Devils, center in the summer of 2007. Not only did they feel they were getting one of the NHL’s best centers, but they were weakening a division rival at the same time.
That was the theory. The reality was a lot different.
Part of the problem was the expectations that went along with a contract worth $7.5 million per season — one that was signed the same day they inked Drury. Gomez had broken the 20-goal mark just once in eight seasons with the Devils, but he was expected to put the puck in the net more in his new home. But it didn’t happen. He matched his career high with 70 points in his first season at the Garden but scored just 16 goals. He equaled that goal total in 2008-09 but saw his assists (42) and points (58) fall off despite seeing his ice time bumped up to more than 21 minutes a game.
By now, Garden fans were bemoaning spending top dollar on a playmaking center who was over 30 and likely entering the back nine of his career — with a commitment of $35 million still on the books.
The only thing that saved Sather was that he was able to foist Gomez off on another team. The Canadiens needed a middle-six center and took Gomez off his hands in what looked like a salary dump. But part of the return was a college defenseman named Ryan McDonagh – who turned into a stud.
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3. Another Devil Disaster
The Signing: Rangers signed center Bobby Holik to a five-year contract
Date: July 1, 2002
Why it mattered: The center on the “Crash Line” that helped the Devils win the Stanley Cup in 1995 and 2000 crashed and burned when he took his game across the Hudson River.
Holik was a big, physical center who put up very good offensive numbers for someone who spent most of his time on a checking line. He had averaged 23 goals and 57 points from 1996-97 through 2001-02 and was a plus player in all six of those seasons. With the Rangers’ non-playoff streak at five seasons and counting, Sather threw money at Holik, signing him to a five-year deal worth $45 million. That’s $9 million per season for a 31-year-old who wasn’t a first-line player.
But with a big contract came big expectations — ones that Holik couldn’t meet. His offensive numbers dropped off sharply in 2002-03; though they rebounded in his second season, 25 goals and 56 points weren’t nearly enough to prevent the Rangers from missing the playoffs for a seventh straight season.
When play resumed after the lockout that wiped out 2004-05, the Rangers wasted little time buying out the final two seasons of his contract. Holik spent the next three seasons with the Atlanta Thrashers before a final season with New Jersey. He finished his career with 326 goals and 747 points in 1,314 games as well as two Stanley Cup rings — and a ton of money from a contract that still generates grumbles from Rangers fans of that era.
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2. Fleury Flames Out
The Signing: Rangers signed forward Theo Fleury to a three-year contract (plus team option for a fourth season)
Date: July 8, 1999
Why it mattered: Fleury and the Rangers were a match made in hockey hell.
With the Rangers having missed the Stanley Cup Playoffs in consecutive seasons for the first time in two decades, ownership gave Smith access to the checkbook and told him to go shopping.
Fleury, all 5-foot-6 of him, had helped the Calgary Flames win the Stanley Cup as a rookie in 1989, then spent the next 10 seasons piling up goals and points. He was coming off his fourth 40-goal season in the summer of 1999; the last 10 tallies came with the Avalanche after a late-season trade. That was more than enough for Smith and Garden president Dave Checketts to pursue Fleury and get his signature on the dotted line of a contract worth $7 million annually.
But the personal issues that Fleury, who described himself as “a prairie kid from a town of 1,500,” had handled successfully in Calgary weren’t as easily dealt with under the bright lights of the Big Apple. He struggled on the ice in his first season but found his game in year two and was among the league leaders in goals and points until his season ended when he checked into a substance abuse program.
His third season saw him produce 24 goals and 63 points but pile up 216 penalty minutes amid incidents that included a fight with the San Jose Sharks mascot and leaving the arena instead of going to the penalty box. The Rangers didn’t exercise their option and gave him away that summer to San Jose; he wound up signing with the Chicago Blackhawks but another substance abuse suspension ended his NHL career.
Fleury’s autobiography, released in 2009, explained a lot. He recounted how he grew up poor in Manitoba, was sexually abused by junior hockey coach Graham James, drank and gambled excessively, and used cocaine during his career, including his time with the Rangers (he got sober in 2005).
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1. Creating the AHL’s Richest Player
The Signing: Rangers signed defenseman Wade Redden to a six-year contract
Date: July 1, 2008
Why it mattered: Sather wasted no time signing Redden, a solid top-four defenseman with the Ottawa Senators for more than a decade, when he became a free agent in the summer of 2008. The No. 2 pick in the 1995 NHL Draft had never been spectacular, but he’d reached double figures in goals five times and was a plus player in each of his last seven seasons with the Sens, who had opted to keep him instead of Zdeno Chara in 2006.
Many thought the six years and $6.5 million average annual were a bit on the high side, though not necessarily outrageous, for a 31-year-old. Given the way things turned out, “outrageous” would have been a major improvement.
Redden had a poor season in 2008-09 and was even worse the following season, managing just two goals and 14 points in 75 games. The skills that had attracted the Rangers were nowhere to be found; instead, he looked washed up.
With cap space tight and Redden not producing, the decision was made to bite the bullet and demote Redden and his huge contract to the AHL. For the next two seasons, he was (by far) the AHL’s highest-paid player. He might have stayed there for the remainder of his contract, but the collective bargaining agreement that ended the 2012-13 lockout eliminated most of the benefits of burying a contract in the minors. Instead, the Rangers bought out the final two seasons of his deal.
The St. Louis Blues quickly signed Redden, though they ended up flipping him to the Bruins at the trade deadline. He retired after playing five games during Boston’s run to the 2013 Stanley Cup Final.
Redden’s signing might not be the worst deal in NHL history, but it’s right up there.
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