Unbreakable Dreams: 4 Best Players to Never Win the Stanley Cup

In the world of professional hockey, the Stanley Cup is the pinnacle, a symbol of supremacy and the gravity that pulls every player toward the same goal — to lift the silver chalice above their heads.

Despite the myriad talents that have graced the ice over the years, a select few legends stand as specters of what might have been. This piece is a tribute to the greatest players in history to have never hoisted the giant trophy.

1. Connor McDavid

Connor McDavid

While Connor McDavid is still very much at the peak of his powers, he can be considered one of the greatest players to have never won a championship, but the 27-year-old will certainly be harboring hopes that the moniker he currently has might disappear into thin air come the end of the season.

His Edmonton Oilers are currently sitting pretty in third place in the Pacific Division and with a mighty six games in hand on the table-topping Vancouver Canucks, his side could be catapulted to the division’s summit if they can carry their form into the latter stages of the season.

It’s not looking bad for them, either; many fans are staking their wagers on them taking home a win, and people are already eagerly waiting to bet on their success when the time comes. It isn’t just fans, either – the official bodies are giving them the nod of approval too.

The online Stanley Cup odds providers as Bodog currently make the Canadian outfit the +700 favorites for glory this season, and McDavid will be hoping he can help his side live up to the billing.

Since being selected as the number one overall pick in the 2015 draft at only 18 years old, McSaviour has established himself as the premier hockey player in the world.

He has accumulated numerous accolades throughout his nine years in the big leagues, clinching the Art Ross trophy a mighty five times, including three wins on the bounce heading into the current campaign. But despite his overflowing haul of personal achievements, he has not yet led the Alberta team to victory.

Before his selection, the Oilers had not made a postseason appearance in ten years. McDavid and his team ended that unwanted streak in 2017 and have made the playoffs in each of the past four seasons. In 2022, they made it all the way to the conference finals, but they were ultimately swept by the eventual champion Colorado Avalanche.

The second coming of Wayne Gretzky will be aiming to take his team all the way this term.

2. Marcel Dionne

An offensive juggernaut who graced the rosters of the Los Angeles Kings and Detroit Red Wings, Marcel Dionne had remarkable goalscoring abilities, but they have never translated into glory.

Throughout his career, he’s scored a record-setting 700+ goals and over 1,700 points – placing him fifth all-time – but he hasn’t been able to clinch the Stanley Cup. With nine All-Star appearances, two Art Ross Trophy wins, and an induction into the Hockey Hall of Fame in 1992, his legacy shines bright.

Despite playing for competitive teams, Dionne couldn’t ever see his name etched into the history books. He did come close in 1982 as he led the Cali outfit to the finals, but they were ultimately bested by the New York Islanders in a bittersweet reminder of how cruel elite-level sports can be.

3. Eric Lindros

Eric Lindros

A player who could do it all, Eric Lindros combined the agility of a wing and the physicality of a defenseman, transforming the traditional mold of a centerman. The first overall pick in the 1991 NHL entry draft, his storied career was marked by individual excellence and a quest for team championship that remained unfulfilled.

He won the Hart Trophy in 1995 and an Olympic gold medal with Canada in Salt Lake City in 2002, as well as being named an eight-time All-Star. However, the Stanley Cup remains the one that got away.

Throughout his storied career, it was the Philadelphia Flyers that brought him closest to that elusive championship. However, despite assembling a powerhouse team around him at the Wells Fargo Center, he wasn’t able to get his hands on the trophy.

The closest he came was in 1997 when the Philly outfit knocked off the Pittsburgh Penguins, Buffalo Sabres, and the New York Rangers to reach the finals. But on the grandest stage, his team flopped and was ultimately swept by the Detroit Red Wings. Lindros would never reach the finals again.

4. Phil Housley

Phil Housley

Throughout an illustrious career that saw him star for the likes of the Buffalo Sabres, Winnipeg Jets, and Calgary Flames, Phil Housley never belonged to a team truly capable of a serious Cup challenge.

Despite his reputation for defense, he accumulated over 1,200 points and earned All-Star accolades seven times, a sentiment shared by several other talented players, including members of the Maple Leafs Trio and four Canucks players who recently joined the All-Star roster.

Although he never claimed the Stanley Cup, he did compete for Team USA in the Olympics and World Cup of Hockey, winning the latter in 1996 and finishing with the silver medal in the former six years later.

The closest he came to winning it all was with the Washington Capitals back in 1998. He helped the DC side past the Phoenix Coyotes, St. Louis Blues, and Dallas Stars to punch their ticket to the finals.

But just like Lindors before him, his team came up against a Red Wings team that was in the midst of becoming a dynasty and was duly swept 4-0. Unfortunately for Housley, he has the unwanted record of being the man to make the most appearances in the NHL without ever lifting the Stanley Cup.

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