Six notable NHLers traded right before their teams won the Stanley Cup

We often hear about the moves teams make that help them win the Stanley Cup.
But what about the players that get shipped away, only to lose their chance at spending a night with the 34-pound silver beast?
The adage goes that the Stanley Cup is the hardest trophy to win in sports. Hockey is as random as it gets – and being a superstar alone won’t guarantee you anything. Jarome Iginla, Henrik Lundqvist, Roberto Luongo, Adam Oates, Mats Sundin and Dale Hawerchuk are just a handful of Hockey Hall of Famers who never got to reach the summit, despite a few of them coming within a victory of doing so.
Today, we’re looking at six notable players – a starting lineup, basically – who were moved away in a big trade by a team prior to winning the Stanley Cup. The kicker? None of these six ever got to win hockey’s ultimate prize:
Jocelyn Thibault, G (Dec. 6, 1995)
Trade: Montreal Canadiens acquired Andrei Kovalenko, Martin Rucinsky and Jocelyn Thibault from Colorado Avalanche for Mike Keane and Patrick Roy
It was the trade that shocked the hockey landscape: one of the greatest goaltenders ever, Roy, was headed to Colorado after a colossal, mid-game breakup just days earlier. Suddenly, the Avalanche had their first superstar goaltender. Roy would go on to win two Stanley Cups and a Conn Smythe with Colorado and finished as a Vezina Trophy finalist twice and was a Hart Trophy runner-up once. He was outstanding during the 1996 Cup run, helping further cement himself as a future Hockey Hall of Famer.
But what about Thibault? The Montreal, Quebec native was back in his home province after spending parts of two seasons with the Nordiques. He’d actually go on to play some solid hockey in his 40 games with the Habs in 1995-96 and played what was a career-high at the time of 61 games the following year. But his numbers started to deteriorate over time in Montreal, and with Jose Theodore coming up the ranks, the Canadiens traded Thibault to Chicago in a deal that sent, among others, Jeff Hackett the other way. Thibault would spend five seasons with the Hawks and even made it into the 2003 NHL All-Star Game.
Thibault would get traded to Pittsburgh ahead of the 2005-06 season and would spend the final three years of his career in a backup role before retiring in 2008. He never once made it out of the first round of the Stanley Cup playoffs in his career and only won four postseason games overall – including two in Montreal back in 1996.
Ryan Whitney, D (Feb. 26, 2009)
Trade: Anaheim Ducks acquired Ryan Whitney from Pittsburgh Penguins for Chris Kunitz and Eric Tangradi
Whitney was a key piece of Pittsburgh’s blueline during the team’s Stanley Cup final appearance in 2008, giving the team a nice mix of skill and physicality. The 2008-09 season was a bit more difficult, though, with injuries limiting him to just 27 games. The Penguins needed some scoring help and traded Whitney to Anaheim to get Sidney Crosby his long-time scoring winger in Chris Kunitz. The Penguins went on to get revenge against Detroit and won the Cup, with Kunitz putting up 14 points in 24 playoff games. He’d eventually crack the 60-point club twice and even made it on Canada’s 2014 Olympic-winning roster. Kunitz would win two more Stanley Cups with the Penguins in 2016 and 2017 before eventually finishing with stints in Tampa Bay and Chicago.
Whitney went on to win a silver medal at the 2010 Olympics. But after just 82 games over parts of two seasons, Whitney was traded to Edmonton and never played more than 51 games in a season again. Whitney actually never made the playoffs again after his 13-game run in 2009, meaning he never got the chance to do what he came so close to achieving in 2008. Nowadays, Whitney is one of the NHL’s most prominent media voices.
Zarley Zalapski, D (March 4, 1991)
Trade: Hartford Whalers acquired Zarley Zalapski, John Cullen and Jeff Parker from Pittsburgh Penguins for Ron Francis, Grant Jennings and Ulf Samuelsson
Blessed with one of the greatest names in hockey history, Zalapski made a name for himself quite quickly in the hockey world. He represented Canada at the 1988 Olympics before making the Penguins on a full-time basis the following year. He’d registering two 40-plus point seasons with Pittsburgh and was one of the more physical players on the team’s blueline.
The deal made sense for both teams – Hartford needed an offensive defenseman, and the Penguins wanted a mix of skill (Francis) and toughness (Samuelsson). Zalapski proceeded to put up the two most productive seasons of his career in Hartford, with points totals of 57 and 65. he also cracked the 100-PIM barrier for the first time, too. But by the time he ended up in Calgary in 1994, Zalapski’s game had already fallen off a bit. He’d go on to finish with stints in Montreal and Philadelphia before bouncing around Europe and various North American minor league teams for the final decade of his career.
Zalapski never played more than seven games in a playoff run after leaving Pittsburgh. Meanwhile, Francis and Samuelsson would play key roles in Pittsburgh’s Cups in 1991 and 1992 – with Francis scoring the clinching goal in 1992.
Mike Gartner, F (March 21, 1994)
Trade: Toronto Maple Leafs acquired Mike Gartner from New York Rangers for Glenn Anderson, 1994 fourth-round pick (Alexander Korobolin) and rights to Scott Malone
Gartner was one of the greatest snipers of his generation, tallying 708 goals over 19 seasons. His best years were with the Washington Capitals, where he nabbed his first, and only, 50-goal campaign in 1984-85. Gartner was still a good player with the Rangers, and he had at least 40 goals in each of his three full-time campaigns there. The Rangers were seeking some physicality and playoff experience, and given he won five Stanley Cups with the Edmonton Oilers, Anderson was an excellent choice for the Rangers. He didn’t do anything too special in the Big Apple and had just six points in 23 playoff games, though he had two game-winning goals. He never played a full season in the NHL again, but he at least took home his sixth Cup championship alongside former Oilers teammate Mark Messier.
Gartner never managed to get to the Cup Final. Toronto would make it to the conference final that year but lost in five games to Vancouver. Gartner would struggle the following year before putting up 35 goals with Toronto in his final season with the club in 1995-96. Gartner then a solid year with Phoenix in 1996-97 before retiring after a difficult season the following year. He was inducted into the Hockey Hall of Fame in 2001 and is now known as one of the best players to never win the Stanley Cup.
Tony Amonte, F (March 21, 1994)
Trade: Chicago Blackhawks acquired Tony Amonte and rights to Matt Oates from New York Rangers for Stephane Matteau and Brian Noonan
Amonte had been a big part of the Rangers right out of college, putting up 69 and 75 points in his first two years, consecutively. Of those totals, 68 were goals – and he quickly established himself as a legit NHL star. But the two-time Olympian had a rough 1993-94 season and needed a change of scenery. The Rangers moved him out that spring before breaking the team’s 54-year streak without a championship that June.
Amonte had an excellent run with the Blackhawks, highlighted by seven seasons with at least 60 points. By all accounts, he was a huge part of the team through some of their more uncompetitive seasons and even served as captain for two seasons. He left for the Phoenix Coyotes in 2002-03 and spent some time with Philadelphia and Calgary before retiring in 2007. And while he did end up having the best career of any of the players in the deal, he didn’t get what he craved the most – a Stanley Cup ring.
Blake Wheeler, C (Feb. 18, 2011)
Trade: Boston Bruins acquired Rich Peverley and Boris Valábik from Atlanta Thrashers for Mark Stuart and Blake Wheeler
Wheeler finished his NHL career after a one-year stint with the Rangers last year, mostly playing a depth role. He had a solid run, registering 943 points in 1,172 games over 16 seasons. He is easily one of the most important players in Winnipeg Jets 2.0 history, with one of the highlights being his 68-assist campaign back in 2017-18.
But before he ever set foot in Canada, he was a young middle-six threat for the Bruins. His production fell in each of his three seasons with the team, which made trading him to Atlanta much easier in 2010-11. He’d play some great hockey with the Thrashers in his 23 games there before the team moved to Winnipeg. From there, he posted nine seasons with at least 60 points, including a pair of 91-point campaigns in 2017-18 and 2018-19.
Unfortunately for Wheeler, he never got to do what Peverley did back in 2011 – win hockey’s most coveted prize. The Jets had a good chance in 2018, with Wheeler putting up an impressive 21 points in 17 games. But after that, Wheeler only managed to win one more playoff series with the Jets and was ultimately bought out after the 2022-23 season.

Get ready, hockey fans! The Daily Faceoff Deadline is happening on March 7th from 11 AM to 4 PM Eastern, and you won’t want to miss it. We’ll be LIVE, breaking down every trade and big move as it happens, with instant reactions and expert analysis from the Daily Faceoff crew. Plus, we’ve got special guests lined up throughout the show, offering exclusive insights from some of the biggest names in the game. From blockbuster trades to surprise moves, we’re covering it all. Tune in to the Daily Faceoff YouTube channel and follow Daily Faceoff socials on March 7th to catch all the action!