Top 15 Worst NHL Players To Win Multiple Stanley Cups

The Stanley Cup has been a part of the NHL's existence for almost a century. Since 1917, some of the league's greatest or decent players have hoisted the iconic silver trophy more than once. Whenever a hockey fan thinks of a multiple Stanley Cup champion, legends such as Gordie Howe, Jean Beliveau, and Wayne Gretzky come to mind. But you might not believe how many NHL players who played in the 70s, 80s, 90s, the 2000s and 2010s that won more than one Stanley Cup in their careers.

But you might not believe how many NHL players who played in the 1970s, 80s, 90s, the 2000s and 2010s that have won more than one Stanley Cup in their careers. In the league's salary cap era, Chicago captain Jonathan Toews led the Blackhawks to three Stanley Cup titles in 2010, 2013 and 2015. This past June, Pittsburgh captain Sidney Crosby lifted the Cup for the second time in his career, just seven years to the day that he won his first against Detroit. A select group of NHL players that won the Cup at least once or twice had their share of ups and downs in the regular season or playoffs but would stay dedicated to reaching their ultimate goal in professional hockey. Here is a list of the 15 worst NHL players that won multiple Stanley Cups.

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15 Colin Fraser

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The Philadelphia Flyers selected Colin Fraser 69th overall in the 2003 draft. Fraser would be part of Team Canada's memorable 2005 World Junior team that won the gold medal. Before Fraser played his first NHL game, Philadelphia traded his rights to the Chicago Blackhawks in February 2004, then signed a three-year entry-level deal a year later with Chicago. Fraser played six games in his first two seasons with the Blackhawks, as he split time in the AHL.

Fraser recorded 17 points in 81 games during the 2008-09 season and picked up 19 points in 75 games played during 2009-10. Fraser played two playoff games with Chicago in the 2010 playoffs and would win the Stanley Cup. The 75 regular season games Fraser played in were enough to have his name on the trophy. Chicago traded Fraser to the Edmonton Oilers in 2010 but lasted one season there. In June 2011, the Oilers traded Fraser to the L.A. Kings, scoring two goals with six assists and dressed for 67 games in 2011-12. Fraser played 18 playoff games in L.A.'s run to the 2012 Cup Final vs. New Jersey, as his only career playoff goal came in Game 1 of the final. The Kings won the Cup in 2012 final and Fraser captured his second Cup.

14 Grant Marshall

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Grant Marshall started his OHL career with the Ottawa 67's in 1990-91. Marshall suffered a neck injury in Ottawa's game vs. Sudbury that very season but recorded 83 points in 1991-92. The Toronto Maple Leafs picked Marshall 23rd overall in the 1992 NHL Draft but traded his rights to the Dallas Stars in 1994. Marshall played seven seasons for Dallas, scoring a career-high 13 goals in 1998-99 and helped the Stars win the 1999 Stanley Cup vs. Buffalo. The 1999-00 season for Marshall was the worst of his career, recording eight points in 45 games due to injury. Although Marshall had 37 points in 2000-01, Dallas traded him to the Columbus Blue Jackets in August 2001.

After two productive seasons with the Jackets, they dealt Marshall in March 2003 to the New Jersey Devils. Marshall struggled to record a playoff goal for Dallas but scored his first six playoff goals in 24 playoff games for the 2002-03 Devils, including a series-clinching triple OT goal against Tampa Bay. Marshall's six-goal effort helped New Jersey win the '03 Stanley Cup. The two-time Cup winner retired from the NHL in 2008 and began working for the Devils' alumni.

13 Billy Carroll

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At the 1979 NHL Entry Draft, the New York Islanders picked centre Billy Carroll 38th overall while they built their eventual dynasty. Carroll joined the Islanders in 1980-81, playing 18 games with New York and 59 with the Indianapolis Checkers, then added 12 points in 18 playoff games for the Isles and won his first Stanley Cup in 1981. Carroll scored nine goals and 20 assists in his second season with the Isles and won his second Stanley Cup in 1982 despite scoring four points in 19 playoff games. During the Isles' 1982-83 season, Carroll scored one goal and 11 assists in 71 games and played 20 playoff games en route to his third Cup victory.

Following New York's loss to the Edmonton Oilers in the 1984 Final, they placed Carroll on waivers and Edmonton made a waiver claim for him. Carroll struggled with the Oilers in 1984-85, recording 17 points in 65 games but won another Cup that season. Carroll played two more seasons with the Detroit Red Wings until announcing his retirement as a four-time Cup champion in 1987.

12 Chris Dingman

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The Calgary Flames picked WHL prospect Chris Dingman as the 19th pick in the 1994 NHL Draft. Dingman played his rookie season with Calgary in 1997-98, recording six points and 149 penalty minutes in 70 games. As Dingman spent part of the 1998-99 season with Calgary's minor league affiliate, they traded him to Colorado in February 1999. He played 68 games in 1999-00 and just 41 games in 2000-01 for the Avalanche because of a knee injury. Dingman recorded four assists in 16 playoff games during Colorado's memorable run to the Stanley Cup in 2001. The Avalanche beat New Jersey to win their second NHL championship, and Dingman won his first Cup.

The Avs traded Dingman to the Carolina Hurricanes in June 2001, playing 30 games for Carolina during the 2001-02 season until they traded him to the Tampa Bay Lightning for goalie Kevin Weekes in early March. Dingman struggled to produce offensively, scoring three goals and eleven assists in four seasons with Tampa and won his second championship in 2004. Dingman retired in 2008 after two seasons in Europe.

11 Daniel Carcillo

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During the 2003 Entry Draft, the Pittsburgh Penguins drafted OHL forward Dan Carcillo 73rd overall. Carcillo made his pro debut for the AHL's Wilkes-Barre/Scranton Penguins in 2005-06, recording 311 penalty minutes. In February 2007, Pittsburgh traded the King City native to the Phoenix Coyotes. Carcillo made his NHL debut with Phoenix, recording seven points in 18 games as a rookie in 2006-07. Two seasons later, Phoenix traded Carcillo to the Philadelphia Flyers. The young enforcer recorded 32 points and 414 penalty minutes in three seasons with Philly until he signed as a free-agent with the Chicago Blackhawks in 2011.

Carcillo played 51 games over two seasons for Chicago but got his name engraved on the Stanley Cup for the 2012-13 Blackhawks that beat Boston in six games. Carcillo split the 2013-14 season with the L.A. Kings and N.Y. Rangers, then returned to the Blackhawks for his second stint in late 2014, recording eight points through an injury-shortened season.

Carcillo did not play in Chicago's 2015 playoff run to their third Stanley Cup in six years, but captured the second Stanley Cup of his career. Carcillo then announced his retirement in a heartfelt Players' Tribune article he wrote.

10 Craig Adams

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The Hartford Whalers drafted forward Craig Adams 223rd overall out of Harvard University in the 1996 draft. Adams played four years of college hockey at Harvard while the Whalers moved from Hartford to North Carolina and changed their name to the Hurricanes in 1997. Adams made his NHL debut with Carolina in 2000-01, scoring one goal and 20 penalty minutes taken in 44 games. Adams spent seven seasons with the Hurricanes but signed with the Anaheim Mighty Ducks in 2005. But the Ducks traded Adams back to Carolina before the 2005-06 season started, recording 21 points and won his Stanley Cup for the Canes in 2006.

He played all 82 games with Carolina in 2006-07, recording 14 points and a rating of -9. Carolina traded Adams to Chicago in January 2008. A year later, the Pittsburgh Penguins claimed Adams off waivers. Adams recorded five points with 16 PIMs during Pittsburgh's run to the Stanley Cup Final, as he won his second Cup against the defending champion Detroit Red Wings. Adams played five more seasons for Pittsburgh until he retired following the 2014-15 season, finishing his NHL career with 160 points in 951 games.

9 Grant Jennings 

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Defenseman Grant Jennings is another former Penguin that makes this list. Jennings made his NHL debut with the Washington Capitals in the 1988 Stanley Cup Playoffs. Washington traded Jennings to the Hartford Whalers before the 1988-89 season. Jennings collected 27 points in 163 games during his three seasons for Hartford until they traded him with Ron Francis and Ulf Samuelsson to the Pittsburgh Penguins on March 4, 1991.

Jennings recorded a minus-13 rating in 44 games for the Whalers but posted a plus-2 rating in 13 games for the Pens in 1990-91. Jennings scored one goal and an assist to help Pittsburgh win the Stanley Cup against the Minnesota North Stars in 1991. Jennings had four goals and five assists in 53 games for the 1991-92 Pens. Despite recording zero playoff points in the 1992 playoffs, Jennings won his second Stanley Cup in his career. Jennings began to decline after the '92 Cup win, scoring two goals and nine assists in his last three years with Pittsburgh. He played his final two NHL seasons with the Toronto Maple Leafs and Buffalo Sabres.

8 Joey Kocur

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Joe Kocur began his junior hockey career with the WHL's Saskatoon Blades in 1982-83, scoring 63 goals in two seasons with Saskatoon. In the 1983 draft, Kocur was picked 91st overall by the Detroit Red Wings and spent his first seven seasons with the organization. A member of the Red Wings "Bruise Brothers" with Bob Probert, Kocur scored a career-high 16 goals and 20 assists in the 1989-90 season. Detroit traded away Kocur to the New York Rangers in March 1991 and won his first Stanley Cup title in 1994. Kocur collected just two points and 17 penalty minutes in 20 playoff games, as the Rangers won in seven games against the Vancouver Canucks. Two years later, the Rangers traded Kocur to the Canucks for Kay Whitmore and played seven career games there.

In December 1996, Kocur signed with the Red Wings as a free agent and helped them win back-to-back Stanley Cups in 1997 and '98. Kocur retired from the NHL in October 2000 with three Stanley Cups, 162 career points and 2,519 penalty minutes in 820 games.

7 Jay Caufield

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Jay Caufield did not play hockey for the University of North Dakota but played five years of college football at linebacker. Caufield graduated from UND with a bachelor's degree in management, then signed as a free agent with the New York Rangers in October 1985. They sent Caufield to the minors in 1985-85 but made his debut with the team in '86-'87, recording three points and 45 penalty minutes in 13 games.

New York traded him to the Minnesota North Stars in October 1987, playing 65 games for their IHL affiliate in Kalamazoo. The Pittsburgh Penguins acquired Caufield through a waiver draft the next season, playing 58 games and recorded 285 penalty minutes. Caufield recorded four penalty minutes per game and scored just three goals in five seasons with Pittsburgh. But he would win two Stanley Cups with the Penguins in 1991 and '92. Caufield retired after the 1993-94 IHL season, made an appearance in the 1995 film Sudden Death and found work as a TV analyst for Penguins games.

6 Tim Taylor

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Originally a 1988 draft pick of the Washington Capitals, Tim Taylor began his pro career with their AHL's Baltimore Skipjacks with 67 points in back-to-back years, then recorded a 100-point season for the Adirondack Red Wings in 1993-94. Nicknamed "Tool Time" for the character on TV's Home Improvement, Taylor made his NHL debut for the Detroit Red Wings in 1994-95, recording 36 points over three seasons combined with Detroit. Taylor captured his first Stanley Cup after 44 games played in 1996-97. Taylor played his next four seasons with the Boston Bruins and the N.Y. Rangers until they traded him to the Tampa Bay Lightning in 2001.

Taylor recorded eight points in 48 games throughout 2001-02 but played 82 games with Tampa for three straight seasons, recording 22 points in 2003-04 along with five playoff points as the Bolts won their first Stanley Cup. The Lightning named Taylor team captain two years after winning the Cup, but a hip surgery caused the two-time Cup champion to retire in 2008. Taylor currently serves as Director of Player Development for the St. Louis Blues.

5 Tomas Kopecky

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The Detroit Red Wings picked Slovakian-born forward Tomas Kopecky in the second round of the 2000 draft. Kopecky made his NHL debut with Detroit in 2005-06 and scored his first career goal in 2006-07. Kopecky scored five goals and seven assists in 77 games for the 2007-08 Red Wings but won his first Stanley Cup, despite not playing a game in the 2008 playoffs. He recorded 19 points in 79 games during the Detroit's 2008-09 season but notched one assist in eight playoff games.

In July 2009, Kopecky left Detroit as a free agent and signed a two-year deal with the Chicago Blackhawks on the day his former Red Wings teammate Marian Hossa signed a 12-year deal with Chicago. Kopecky did not much of an impact offensively for the 2009-10 Blackhawks, recording 21 points in 74 games. However, Kopecky scored six points in 17 playoff games and claimed his second Cup in three seasons. Even though Kopecky had 42 points the next season, Chicago traded the two-time Cup winner to the Florida Panthers in June 2011. Kopecky recorded 79 points in four seasons with the Panthers.

4 Jean Potvin 

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Jean Potvin, the older brother of Hockey Hall of Fame inductee Denis Potvin, played three seasons of junior hockey with the Hull Volants and Ottawa 67s from 1966-69. Potvin signed as an undrafted free agent with the Los Angeles Kings in November 1969. Potvin spent two seasons in L.A., recording a career-low minus-39 rating in his rookie year. The Kings traded him to the Philadelphia Flyers on January 28, 1972.

Potvin played 64 games for Philly until they shipped him to the New York Islanders in March 1973. Jean's younger brother Denis did not join the Isles until 1973-74 but broke out in 1975-76 with an impressive 72 points in 78 games, including a hat-trick performance vs. Detroit. The Islanders traded Jean Potvin to the Cleveland Barons in 1978, then transferred to the North Stars, but he returned to Long Island as a free agent before 1979-80. Potvin won two Stanley Cups in 1980 and '81, then called it a career.

3 Wendell Young

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The Vancouver Canucks drafted goaltender Wendell Young out of the Kitchener Rangers in 1981. Young would make his Canucks debut in the 1985-86 season win four wins, nine losses, and three ties in 22 games along with a 3.58 GAA. Young did not play in the NHL full-time until the 1989-90 season for the Pittsburgh Penguins, appearing in 43 games as their no.1 goalie. Young lost the starting goalie job with the Penguins but stayed on their roster as a backup, earning two Stanley Cup rings in 1991 and 1992.

The Tampa Bay Lightning claimed him in their 1992 Expansion Draft and played 40 games in two years with the young franchise, and played his last NHL season for Pittsburgh in 1994-95. Even though Young sported a mediocre record of 59-86-12, he remains the only player in hockey history to win four North American championships: The Memorial Cup in 1982, the Calder Cup in 1988, the Stanley Cup in 1991 & '92 and the Turner Cup twice.

2 Stephane Yelle

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Stephane Yelle came to the NHL as a draft pick of the New Jersey Devils in 1992. Before Yelle could play his first NHL game, the Devils traded him to the Quebec Nordiques two years later but didn't play a single game there because they relocated to Denver in 1995. The Bourget, Ontario native made his debut for the Colorado Avalanche in 1995-96, recording 27 points in 71 games. The Avs went to the 1996 Stanley Cup Final against the Florida Panthers and won it in four games. Yelle won his first career Stanley Cup with the 1995-96 Avalanche, recording one goal and four assists in 23 playoff games.

Yelle continued to work on his checking and penalty killing abilities for Colorado but failed to reach the 25-point mark from 1996-97 to 2001-02. However, Yelle won another Stanley Cup in 2001 despite playing 50 regular season games. The Avs traded Yelle to the Calgary Flames in October 2002 and led them to the 2004 Cup Final vs. Tampa Bay, but lost in seven games. After stops in Boston and Carolina, Yelle returned to the Avalanche and retired after the 2009-10 season.

1 Dustin Penner 

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The list ends with another former L.A. King forward Dustin Penner, who played one year of college hockey for Minot State-Bottineau then transferred to the University of Maine. The Anaheim Mighty Ducks signed the 6'4" forward as a free agent in May 2004 and made his NHL debut with Anaheim in 2005-06. Penner scored seven points in 19 games, then had a productive 2006-07 season with 29 goals and 16 points in 82 games. Penner won the first Stanley Cup of his career with eight points in 21 playoff contests. In 2007, Penner left the Ducks as a restricted free agent and signed a five-year, $21.25 million deal with the Edmonton Oilers on August 2nd.

Penner struggled in his first two years with Edmonton, scoring 47 points in 2007-08, and recording 37 points during the 2008-09 season. But Penner collected a career-high 63 points in 2009-10. Edmonton traded Penner to the LA Kings in February 2011. Despite hurting his back while eating pancakes, he won another Cup in 2012 scoring three goals and eight assists for the underdog Kings.

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