
The Connor McDavid Era in Edmonton Reaches a Turning Point
Connor McDavid is still chasing his first Stanley Cup Championship. With free agency looming in 2028, do the Edmonton Oilers or another team give McDavid the best chance of capturing that ultimate prize.

Connor McDavid, the veteran Edmonton Oilers center, is a generational talent who has yet to win a Stanley Cup.
Looking at the NHL records for career points, McDavid’s 1,220 points rank 47th among the all-time greats. It's only taken 749 games to achieve this, and he doesn't turn 30 until January. However, during his 11 seasons in an Edmonton uniform. McDavid has only played in two Stanley Cup Finals, losing both times to the Florida Panthers. After getting so close during the previous two seasons, the Oilers were eliminated in the first round by the Anaheim Ducks.
Does individual greatness outweigh winning championships? McDavid, who can become an unrestricted free agent in 2028, is still in the prime of his career.
If McDavid were to maximize his chances of winning a championship by 2028, does Edmonton give him his best opportunity, or is it time for a change of scenery?
We take a closer look at both scenarios

Connor McDavid is among the NHL all-time greats
McDavid has registered 1,220 career points (409 goals, 811 assists) in 749 games. Wayne Gretzky is still No. 1 all-time with 2,857 career points.
Gretzky spent the first nine years of his career with the Oilers and remains Edmonton’s all-time points leader with 1,669. McDavid ranks No. 2. Like Gretzky, McDavid’s career résumé includes several individual accolades.
Connor McDavid Accolades
| What McDavid Won | Year |
|---|---|
| Conn Smythe Trophy | 2024 |
| Art Ross Trophy | 2016-17, 2017-18, 2020-21, 2021-22, 2022-23, and 2025-26 |
| Hart Memorial Trophy | 2016-17, 2017-18, 2020-21, and 2022-23 |
| Ted Lindsey Award | 2016-17, 2017-18, 2020-21, and 2022-23 |
| Maurice “Rocket” Richard Trophy | 2022-23 |
McDavid is also one of three NHL award finalists for the 2025-26 Ted Lindsey Award, which goes to the league’s most outstanding player.
Why winning a Stanley Cup by 2028 matters
In October, McDavid signed a two-year extension with Edmonton that pays him $12.5 million per season. That gives the Oilers two more seasons to bring home the franchise's first Stanley Cup since the 1989-90 season.
If Edmonton wins a championship before McDavid’s contract is up, he would likely be willing to stay put. At the same time, McDavid needs that Stanley Cup win so his name isn't added to the list of great NHL players who never won a championship.
This season might get a mulligan as McDavid was playing through a fracture in the foot and ankle area. The team captain admitted during the team's final media session that he didn't have that speed burst against the Ducks. After the season-ending loss to Anaheim, McDavid said the Oilers were “an average team with high expectations.”

Evaluating best fits for Connor McDavid
Let's be clear, the top NHL betting sites don't have a Connor McDavid next team market. With 2028 only being two years away, we are proposing five teams that could be the best fits for McDavid should the player and team decide to part ways.
We considered the following criteria when putting together this list:
- Stanley Cup contender
- Cap flexibility
- Supporting roster
- Organizational stability
- Team needs
- Market size

Top 5 NHL Teams that should consider adding McDavid
New York Rangers
Projected 2026-27 cap space: $26.97 million:
2025-26 results: Missed the postseason
Madison Square Garden is an arena built for superstar players. The New York Rangers are in desperate need of players willing to put the team on their back and lead them to the postseason - a place the Blueshirts haven’t been since the 2023-24 season. NHL markets don’t get much bigger than the Big Apple, and there's a good chance that McDavid (like Gretzky before him) would shine on Broadway.
Colorado Avalanche
Projected 2026-27 cap space: $2.98 million
2025-26 results: Still alive
If you’re wondering why we would include Colorado being that the team only has $2.98 projected salary cap space for next season. It’s because of the following season that the number becomes $37.78 million. Plus, the Avalanche earned the President’s Trophy for best regular-season record. The roster already includes two of the NHL’s regular-season points leaders in Nathan MacKinnon (127) and Martin Necas (100). Scott Wedgewood led all NHL goalies in save percentage (9.21). This is a team that’s built to win now.
Toronto Maple Leafs
Projected 2026-27 cap space: $22.24 Million
2025-26 results: Missed the playoffs
Yes, Toronto has won the Stanley Cup 13 times, but the current championship drought is at 59 years and counting. We’re talking about the same Toronto Maple Leafs that have the highest valuation out of 32 NHL Clubs at $4.3 billion. Plus, we’re talking about a large market team that isn’t producing the championship results, which happens in every major pro sport. Maybe it’s time to start thinking about the possibility of luring McDavid over to Ontario as the centerpiece to those future championship plans.
Florida Panthers
Projected 2026-27 cap space: $15.38 million
2025-26 results: Missed postseason
Sure, it sounds like a crazy idea that McDavid departs Edmonton and wins the Stanley Cup with the franchise that shattered his championship dreams twice. The Panthers front office would need to free up some additional cap space as the $15.38 million wouldn’t be enough to sign McDavid and make additional moves to fill out the roster. This was one of those off years in South Florida as several key players, including Matthew Tkachuk and Aleksander Barkov, missed significant time due to injuries.
Philadelphia Flyers
Projected 2026-27 cap space: $39.45 million
2025-26 results: Eliminated in second round
McDavid and the Flyers share something in common - they’re starving to win a Stanley Cup as the current drought dates back all the way back to 1975. The Flyers weren’t even expected to make the postseason this year, but they made it to the second round before being eliminated by the Carolina Hurricanes. Philadelphia is showing signs of being a young club on the rise, which includes breakout star Porter Martone. One thing the Flyers could desperately use is a player like McDavid as Travis Konecny finished the regular season with just 68 points to lead the team.

Staying in Edmonton still makes perfect sense
It's not like McDavid is saying he wants out of Edmonton. Sure, the Oilers took a big step backward from the previous four seasons highlighted by two trips to the Stanley Cup Finals and three Western Conference championship series appearances.
The combination of McDavid and Leon Draisaitl on Edmonton’s top line is a potent combination as both players finished the regular season ranked among the NHL’s top-10 points leaders. McDavid ranked first with 138 points and Draisaitl was ninth with 97. With Edmonton, the bigger issue is finding the right supporting players to help the franchise complete the championship puzzle.
With McDavid playing his entire career in Edmonton, winning there would certainly carry more weight than joining another contender. Plus, it would cement his legacy as another one of the Oilers all-time greats who won a Stanley Cup.

Stanley Cup Championship is the missing piece
The biggest unknown regarding McDavid’s career is if and when he’ll win a Stanley Cup before he retires. It’s really the only thing he has yet to achieve as a pro.
At some point, NHL fans are going to stop asking “How good is McDavid?” as his career achievements make it crystal clear that he is one of the all-time best players. If the Oilers don't win a Stanley Cup soon, those same fans might very soon start asking a different question: “Where can Connor McDavid win a Stanley Cup?”

Bill is an experienced iGaming journalist who has covered the launch of legal sports betting in New Jersey and Pennsylvania, including ribbon-cutting ceremonies and first-bet events. His reporting has featured interviews with executives from BetMGM, Hard Rock, and DraftKings, with work appearing on Covers, Mass Live, Legal Sports Report, TheLines, Deadspin, PlayNJ, and more.
A lifelong Eagles fan, Bill counts covering the 2018 Philadelphia Eagles Super Bowl Parade among his career highlights.
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