June 23, 2025 by Ryan Lotsberg

No team had lost consecutive Stanley Cup Finals since the Boston Bruins did so in 1978 and 1979 until the Edmonton Oilers did just that by losing Game 6 of the 2025 Stanley Cup Final.

Many people felt that the Oilers would get the job done this time around because they had been there before. That’s how it usually goes, right? The experience of losing in Game 7 of the 2024 Stanley Cup Final made them stronger, and they learned the lessons offered by such a heartbreaking defeat. The consensus was that the best player in the world, Connor McDavid, wasn’t going to let his team lose twice in a row.

All professional athletes deal with pressure, but there’s an extra level of pressure heaped upon players like McDavid because of how talented they are.

“That’s a pretty heavy question” replied McDavid when asked about the extra pressure of being the greatest player in the world prior to Game 6. “I don’t think about it that way. If you think about it that way, you’d be probably pretty crippled in terms of how you prepare and how you play.” He might not think about it that way, but I’m sure he’s aware that’s how the media and the fans think.

McDavid went as far as to guarantee a win in Game 6 on a TNT interview, but that wasn’t the outcome. McDavid was one of the most dangerous Oilers in Game 6, but he didn’t register a point. He got seven points in the six game series, but that’s below his career playoff points per game rate of 1.56. McDavid only scored one goal in the Stanley Cup Final, which matched his output from last year’s series. He didn’t get a point in Game 7 of last year’s series either. He led last year’s series in points (11), but didn’t even lead his own team in points in this year’s series. The bottom line is that McDavid hasn’t found a way to lead his team to a championship in two Stanley Cup Final appearances over his ten year career.

There’s a lot of talk about legacies when we’re evaluating great players like McDavid. Individual accolades are important; but championships are the be all, end all in any conversation about legacies. Being the captain and the face of the first franchise to lose in back to back Stanley Cup Finals since the late 1970’s isn’t a positive start to McDavid’s story, but we have to realize that there’s a lot of time left for McDavid’s story to be written.

Take LeBron James for example. He was a prodigy when he was drafted into the NBA in 2003. He lost in his first two NBA Finals appearances in 2007 and 2011 before finally winning one in 2012. James has gone on to break the NBA’s all-time scoring record and win four NBA championships.

Steph Curry, the NBA’s all-time three-point field goal leader, has also won four NBA championships. He has lost two NBA Finals in his career as well.

Tom Brady won seven Superbowls, which is more than anyone else has ever won. He won his first three Superbowl appearances, but he lost his next two. Both of those losses were to the New York Giants. He won four more Superbowls after losing those two to the Giants.

We know that Wayne Gretzky lost his first Stanley Cup Final in 1983 and then won his first Stanley Cup in 1984. He won four Stanley Cups with the Oilers, but he also lost a second Stanley Cup Final with the Los Angeles Kings in 1993. Overall, Gretzky was 4-2 in Stanley Cup Finals.

None of the players in these examples lost in back to back years like McDavid just did, but his story is different from anyone else’s story. We like to connect the greatest players to each other for the sake of comparison, but each person on this planet has their own story.

McDavid will obviously not end up with a legacy matching the incomparable legacy of Michael Jordan (6-0 record in NBA Finals). These two losses in the Stanley Cup Final will be held against him in any conversation about the greatest legacies in hockey history, just like James’s six NBA Finals losses will always be held against him in basketball’s “greatest player of all-time” debate. There’s absolutely no reason that McDavid can’t finish his career with similar resumes to the other great athletes that I’ve mentioned here though. Jordan won his first NBA Championship at the age of 27. McDavid is currently 28. There’s still a lot of time left for McDavid to do his winning. I wouldn’t be surprised if he was to win as many or more Stanley Cups than the Panthers have by the time it’s all said and done.

The question is whether or not those Stanley Cup wins will be won with the Oilers. McDavid is about to enter the final year of his current contract. He will be eligible to sign an extension with the Oilers as of July 1. McDavid was obviously asked about his contract situation during his season ending media availability. He gave some standard answers about needing to talk to his agent and his family first before making any decisions on his future, and he said that he needs to take care of himself and his family first. Those words might concern some Oilers fans, but they’re exactly what any player entering a negotiation would say.

When McDavid was asked if he has unfinished business here, he said “Absolutely, absolutely yeah. This core has been together for a long time and we’ve been building to this moment all along. The work that’s gone on behind the scenes, the conversations, the endless disappointments, and you know some good times along the way obviously as well… We’re all in this together trying to get it over that finish line… of course there’s unfinished business here.”

In response to a follow up question, he said that “I get up here every year and tell you that it’s all about winning, and it’s only about winning, and we won’t be satisfied until that’s done.” Ultimately, winning is the most important thing to McDavid. “If I feel there’s a good window to win here over and over again, then signing is no problem.”

Some teams might have the cap space to sign McDavid should he decide to hit the open market next summer, but I highly doubt those teams would be in a better position to win than the Oilers. It’s so rare that players of McDavid’s stature leave the instant they hit UFA status. Such players moving on to contending teams near the ends of their careers happens far more often, but McDavid isn’t there yet. There’s something to be said for the emotional connection to a franchise and a city when a team is built around you and you’ve been building towards something great for so many years. The desire to finish what he started here will likely factor into his decision. I’m honestly not concerned about McDavid leaving at this time.

When a player like McDavid wants to win as badly as he wants to win, it’s just a matter of time until he does it. I’m confident that it will be in an Oilers uniform.

Before the Stanley Cup Final started, I wrote a piece about McDavid having the chance to answer the questions that hang over him about his ability to win. I wrote about how coming so close to achieving a goal like winning a Stanley Cup makes you ask yourself some hard questions that elicit meaningful changes that yield the desired results. Clearly, there are still some questions that McDavid and the Oilers need to ask and answer about what it takes to win.

Related: McDavid and the Oilers have a chance to put the questions to rest

They will obviously take some time to decompress and process the disappointment of having fallen short of their ultimate goal once again, but McDavid and the Oilers will spend the summer ruminating about what it takes to win so that they will be able to get the job done when their next opportunity comes around.

When those questions get answered, we’ll truly begin to see McDavid write his legacy.