Connor McDavid participates in practice with the Edmonton Oilers on July 4, 2015. Photo by Connor Mah.
Written by Derrik Maguire
On Monday night, Connor McDavid and the Edmonton Oilers defeated the New York Rangers 3-1 on home ice. McDavid opened the scoring in the first period after a Rangers turnover, extending his season-opening point streak to 19 games. After Edmonton built a 2-0 lead, New York cut the deficit in half five minutes into the second period.
The score remained 2-1 until late in the third period, when the Oilers killed off a penalty as the Rangers pulled their goaltender. During a 6-on-4 opportunity, McDavid challenged a loose puck in the defensive slot, forcing a weak pass toward the point. Leon Draisaitl intercepted it and scored an empty-net goal to secure the victory.
Through Edmonton's first 19 games, McDavid has recorded an astounding 48 points, including 11 goals and 37 assists. Although he failed to record an assist for the first time this season, his 18-game assist streak was tied for the second-longest in NHL history. McDavid also became the fourth player in league history to open a season with a point streak of at least 19 games, joining Dany Heatley, Mats Sundin, and Wayne Gretzky.
McDavid's numbers are extraordinary, yet the hockey world continues to place expectations on him that few players could ever live up to. Despite everything he has accomplished individually, conversations surrounding his greatness continue to return to one achievement he has yet to reach: winning the Stanley Cup.
Long before McDavid became an Edmonton Oiler, Gretzky recognized the potential of the young Canadian forward. When Edmonton won the 2015 NHL Draft Lottery, Gretzky was among those publicly praising the player who would soon become the face of the franchise.
"He's as good as I've seen in the last 30 years, the best player to come into the league in the last 30 years, the best to come along since Lemieux and Crosby. He can definitely change a franchise's fortunes," Gretzky said in 2015.
Gretzky went even further, expressing his hope that McDavid would bring a championship back to Edmonton.
"I hope he brings Edmonton a Stanley Cup and he breaks my records … he's got the talent and the makeup to do it. I hope he leaves a couple for me, though. I could use that."
McDavid wasted little time establishing himself as one of the league's best players. Within his first two seasons, he had already won an Art Ross Trophy and a Hart Memorial Trophy. His individual accomplishments continued to grow, but the expectation of a championship remained.
That expectation became even more personal in 2020, when McDavid sat down with Gretzky for a one-on-one conversation with GQ. During their discussion, McDavid asked what it felt like to win a Stanley Cup in Edmonton. Gretzky's response was more than a reflection on his own career. It was a prediction about McDavid's future.
"When you guys do win - and you will win a Stanley Cup - the feeling is just over the top," Gretzky said. He continued, "but when you actually lift the Cup, it's pretty special, and you will lift it one day because you're too good."
Having the greatest player in hockey history tell you that you are too good not to win a Stanley Cup speaks to the expectations surrounding McDavid. Gretzky has continued to express that belief, most recently praising the Oilers captain following his impressive start to the 2026-27 season at the Hockey Hall of Fame.
"What he's doing for his hockey team, and for the game, and for the city of Edmonton, it's unmatched right now. I think he's on a mission to win a Stanley Cup. He wants it desperately," Gretzky said.
However, the expectations surrounding McDavid extend beyond the Oilers. He has also inherited the responsibility of becoming the defining player of his generation.
Over the past four decades, hockey has seen several generational Canadian talents carry the game forward. Gretzky defined an era throughout the 1980s with Edmonton and continued his dominance into the 1990s. Along the way, he also represented Canada on the international stage, winning multiple tournaments, including the 1987 Canada Cup.
Mario Lemieux followed, becoming one of the defining players of his generation with the Pittsburgh Penguins throughout the late 1980s, 1990s, and early 2000s. Like Gretzky, Lemieux represented Canada at the 1987 Canada Cup before adding more international accomplishments to his career.
As Lemieux's career progressed, another generational talent emerged. After Pittsburgh selected Sidney Crosby first overall in the 2005 NHL Draft, Lemieux helped mentor the young forward during his first season with the Penguins. Crosby went on to become the defining player of his generation, leading Canada to several international victories, including the 2025 4 Nations Face-Off.
When McDavid entered the NHL in 2015, it was clear that another generational Canadian talent had arrived. Yet, despite his individual accomplishments, there had not been a defining moment that connected him to Crosby in the same way Crosby had once been connected to Lemieux.
That changed at the 2025 4 Nations Face-Off.
By that point, McDavid had established himself with five Art Ross Trophies and three Hart Memorial Trophies. He had also won the 2016 IIHF World Championship with Canada as a 19-year-old. However, the 4 Nations Face-Off marked his first opportunity to compete in a best-on-best senior international tournament and share the ice with Crosby as a teammate.
In the championship game against the United States, McDavid delivered the overtime-winning goal in a 3-2 victory. The moment drew an immediate comparison to Crosby's golden goal at the 2010 Winter Olympics. Although both players downplayed the idea of a passing of the torch, the moment felt significant to hockey fans across the country.
Just as Crosby had done 15 years earlier, McDavid delivered a defining international moment for Canada. He had established himself as the next generation's leader, carrying forward a legacy that had passed from Gretzky to Lemieux to Crosby.
But there is one accomplishment those three players share that McDavid has yet to experience: winning a Stanley Cup.
Gretzky won four championships with Edmonton in the 1980s. Lemieux captured two with Pittsburgh in the 1990s, while Crosby won three with the Penguins across the 2000s and 2010s.
McDavid has already reached extraordinary heights in his own career, collecting six Art Ross Trophies, three Hart Memorial Trophies, and five Ted Lindsay Awards. He has also brought Edmonton to the Stanley Cup Final in consecutive seasons, 2024 and 2025.
During both playoff runs, McDavid led the league in points. His 42-point performance in the 2024 playoffs ranks among the greatest postseason performances in NHL history, behind only Wayne Gretzky's 1984-85 and 1987-88 campaigns and Mario Lemieux's 1990-91 run. His 34 assists that postseason also established a new NHL record for assists in a single playoff year.
Despite Edmonton falling short against Florida in the 2024 Stanley Cup Final, McDavid was awarded the Conn Smythe Trophy as playoff MVP. It marked just the sixth time in NHL history that the award went to a player on the losing team in the Final and only the second time it was awarded to a skater.
It was another remarkable individual achievement, but it was not the accomplishment McDavid wanted. The goal was never to win the Conn Smythe Trophy. It was to lift the Stanley Cup.
After falling short against the Florida Panthers in consecutive Finals, McDavid remains without the championship that has defined the careers of the players he is so often compared to.
Gretzky helped establish a championship standard in Edmonton, and he has repeatedly told McDavid that he believes he can achieve that same level of success. McDavid has already delivered a defining moment for Canadian hockey. Now, he is still searching for the moment that will define his legacy in Edmonton.
The pressure also extends beyond the Oilers. McDavid is not only the captain of one of Canada's most successful NHL franchises but also the face of a generation of Canadian hockey. With the Montreal Canadiens' 1993 championship remaining the last time a Canadian team won the Stanley Cup, the possibility of ending that drought adds another layer to the expectations surrounding Edmonton.
It is not a responsibility McDavid has publicly claimed, nor is it something he can accomplish alone. However, when considering which Canadian franchise has the best opportunity to end the drought, Edmonton is inevitably part of the conversation. Much of that belief comes from the player wearing its captain's letter.
McDavid has also taken on a larger leadership role with Canada's national team, wearing the captain's "C" in the Olympic semifinal that Crosby missed. His responsibilities now extend across both the professional and international stages, further cementing his place as the leading Canadian player of his generation.
Through the opening 19 games of the 2026-27 season, McDavid's 48 points have him on pace to reach the 200-point mark, a milestone achieved only by Gretzky and Lemieux. Whether he reaches that number is almost secondary to the larger goal he continues to chase.
Winning a Stanley Cup is not necessary to validate what McDavid has already accomplished. His greatness is undeniable, and his individual résumé is already among the most impressive in NHL history. But the more he achieves, the greater the expectation becomes that he will eventually deliver a championship to Edmonton.
Six years ago, Gretzky told McDavid that he would win a Stanley Cup one day. Today, that prediction remains unfulfilled. For a player who has accomplished nearly everything else, the championship that could further define his legacy is still waiting.
