What would a Stanley Cup and second Conn Smythe Trophy do for Connor McDavid’s legacy?

May 21, 2025, 09:00 EDT

Credit: May 14, 2025; Las Vegas, Nevada, USA; Edmonton Oilers center Connor McDavid (97) skates against the Vegas Golden Knights during the first period of game five of the second round of the 2025 Stanley Cup Playoffs at T-Mobile Arena. Mandatory Credit: Stephen R. Sylvanie-Imagn Images

They say time flies when you’re having fun.

Somehow, it’s been a full decade that Connor McDavid has wowed us with his peerless combination of speed, skill, and playmaking at the NHL level. For the third time in four seasons, his Edmonton Oilers are among the final four playoff teams. After a crushing Game 7 defeat in the Final last spring, McDavid continues to seek the ultimate, elusive jewel in his crown — the Stanley Cup.

Get DFO’s latest Conn Smythe odds here!

The Oilers’ captain could retire today and be among the greatest to ever play the sport. But at 28 years old and nearing the end of his physical prime, the next few weeks are critical to his story. We’re asking the question: How would a Stanley Cup (and second Smythe Trophy) change McDavid’s legacy?

🐐 The G.O.A.Ts

The short list of the NHL’s greatest of all-time typically starts with three names: Wayne Gretzky, Bobby Orr, and Mario Lemieux. Sidney Crosby and Gordie Howe often compete for the fourth spot on hockey’s Mount Rushmore. Curiously, goaltenders and non-Orr defensemen always take a back seat.

There are no wrong answers. Given the subjectivity and generational divides in these debates, it’s more fun to have the conversation than to solve it.

But as always in this space, bringing evidence and objectivity to the chat adds credibility to opinion. Having done exhaustive research for a half-decade on quantifying performance across generations and neutralizing scoring by era, I’m going to start with a few guidelines:

We’re going to consider McDavid among forwards only.
No projecting. We’re not looking beyond the next month.
McDavid is already among the seven best NHL forwards ever (listed alphabetically): Crosby, Gretzky, Howe, Jaromir Jagr, Lemieux, McDavid, Alex Ovechkin.
That means McDavid has already passed Jean Beliveau (10 Stanley Cups), Rocket Richard (14-time year-end all-star), Phil Esposito (five scoring titles), Howie Morenz (“hockey’s Babe Ruth”), and well, everyone else, including Joe Sakic, Steve Yzerman, Guy Lafleur, Mark Messier, and Mike Bossy.

While rational cases can be made for many superstar forwards, from a data-driven perspective, our top seven stand alone and will be our focus today.

🏅 Individual Honors

We’ll start with some straight facts about our seven forwards: Hart Trophies (league MVP); Hart finalists (top-three in voting); Art Ross Trophies (points leader); top-three finishes in points-per-game; Richard Trophies (or most goals prior to its creation); Lindsay Awards (most outstanding player as voted by the players); and Conn Smythe Trophies (playoff MVP).

The G.O.A.Ts: You’ll notice more dark blue on the left side of the chart. Howe played in a tiny, all-Canadian NHL, while Gretzky peaked before the mass explosion of European and American talent. To take nothing away from either, it helped to compete against a league with a narrow geographic footprint.

Both Lemieux and Crosby missed serious time during their award-collecting and stat-accumulating peaks. There’s major what-if energy there. But playing a high volume of games at your best is part of an individual’s overall value. Both join Gretzky as having won every honor listed at least twice.

McDavid Watch: McDavid’s been extremely healthy in his first decade. But he did lose the Hart, Ross, and Lindsay to teammate Leon Draisaitl in 2019-20 after a mid-season injury and shortened pandemic schedule. His last two seasons also featured nagging setbacks and enough missed time to hinder award chases.

Yet, only Gretzky (nine), Howe (six), and old-time blueliner Eddie Shore (four) top McDavid’s three Harts. His six finalist nods also stack up well — and he may not be done with MVP-caliber seasons. The same is true of his Ross (five) and Lindsay (four) counts and his nine top-three finishes in points per game. While he’s likely to retire with a solo Rocket, fellow playmaker Crosby surprised with his second at age 29.

McDavid’s individual trophy case and honors are among the greatest of any era. Should he scoop a Smythe in a winning cause (to go with 2024’s in a losing cause), he would start his own club. He’d also join Crosby (2016-17), Lemieux (1991-92), and goaltender Bernie Parent (1974-75) with playoff MVPs in consecutive seasons. A second Smythe would be a monumental addition to his résumé.

🏆 The Stanley Cup

As dominant as McDavid has been, there are some that won’t open the velvet rope to The G.O.A.T. Club until his name is etched on that famous silver mug. He’ll be grouped with Jarome Iginla and Joe Thornton as modern stars with a regrettable career gap. Barry Bonds, Dan Marino, and Charles Barkley know the feeling.

In a 32-team NHL with a salary cap, I’ve never subscribed to this theory — teams win team trophies. But a Stanley Cup ring will inevitably hammer the point home on his reputation as a legend.

The graphic below splits the playoff careers of all-time forwards before and after their age-30 seasons. The visual is eye-opening on how short-lived team success can be for generational talents.

The G.O.A.Ts:

Won 15 rings before turning 30 and just one after turning 30. It seems impossible. These are six of the most enduring talents in pro sports that defied any rational aging curve. Yet, only Ovechkin (age-32 season) won a Cup beyond his 20s.
Most stopped making deep runs after turning 30. Look at those rounds won. Howe’s split? 11-4. Gretzky? 23-7! Jagr won more rounds as a teenager than in his final 13 seasons. Crosby’s 19-1 split is most stunning — his Penguins won a single round after his third Cup at 29.

McDavid Watch: As Yogi Berra once said “It gets late early out there.” History suggests McDavid’s Oilers are on borrowed time. The sport’s best rarely carry teams to Cups once they blow out their 30th birthday candles. In McDavid’s case, he’ll be 30 in January 2027. Draisaitl turns 30 in six months.

Now, nothing prevents McDavid from winning a Cup in his 30s. Ovechkin did it — his only meaningful team success came at 32. Yzerman won his first of three titles at 31 but it took an army of Hall of Famers not possible in a cap world. Messier snared a sixth Cup at 33. But the best Cup-chasing years fade faster than we realize. Just ask Crosby and Evgeni Malkin, or Chicago‘s Patrick Kane and Jonathan Toews.

📈 McDavid’s Place in History

McDavid is still 28 years old. He could play another 12 years, become the second-highest point scorer of all-time, compete for a half-dozen more MVPs and scoring titles, win multiple Cups and win multiple Olympic golds. Look at the incredible impact Crosby and Ovechkin have had through their 30s, elevating their statuses.

Here are the responses to today’s headline question in a poll on X last week:

⚡️ POLL: Always curious & often write about legacies… What would a Stanley Cup + 2nd Smythe do for McDavid's G.O.A.T. 🐐 status?

— Paul Pidutti (@AdjustedHockey) May 15, 2025

Whoa. It’s clear how much a McDavid Cup/Smythe combo means to the public. But it’s easy to get caught up in the moment. After all, it’s early in his career (712 games) for that kind of declaration. Should there be a parade in McDavid’s hometown of Newmarket, Ontario, reaching Crosby/Howe territory overnight may be generous. Leaping two-decade superstars in half the time requires major projecting.

So, let’s take a systematic approach. With PPS — my comprehensive career ranking methodology — we can get a sense of where McDavid stands today without the hype getting in the way. Here’s #97’s ranking in the system currently — and with a Cup/Smythe added (+10 in PPS).

This feels right. In 2023-24, McDavid went from #15 to #9, passing Richard, Beliveau, Brett Hull, Yzerman, and Sakic. This season, he passed Esposito and Morenz, now firmly the #7 forward all-time. A Cup and second Smythe adds +10, so he’d move to 368 — just 15 back of Ovechkin. Another playoff disappointment leaves McDavid taking a slower route to catch Ovie at #6.

But you can see why everyone wants to pontify (hey, the Pope is red-hot these days) McDavid. His Peak score (97) — a player’s seven best seasons — has edged Crosby (96), Howe (92), and Ovechkin (91). It suggests McDavid’s very best is a tick above. But 2024-25 was also just his seventh-best season, so we’ve potentially now seen his full prime, and his Peak score shouldn’t move notably upward.

The methodology was designed so that player needs to continue to build up Career score (i.e., productivity) without completely tanking their Pace score (i.e., efficiency). It’s why McDavid — with only 10 seasons and 361 career goals — remains behind the greatest goal scorer of all-time (Ovechkin) and the second-highest point-scorer in history (Jagr). There’s still work to do to hang with the G.O.A.Ts.

💭 Closing Thoughts

Connor McDavid’s first NHL decade has put him on a path to being a top-three forward. A perfect next few weeks will accelerate that trajectory. But we need to pump the brakes. Even after crossing best-on-best international title and potentially Stanley Cup off his bucket list, there are five other forwards that endured at a comparably high level for much longer. And in Lemieux’s case, a much higher level for slightly longer.

McDavid’s reputation would soar with a Cup and Playoff MVP. But even with a title, it will take another half-decade of good health and elite play before we can make any plans to legitimately carve him onto Mount Rushmore. In the mean time, his pursuit of a ring will continue to thrill.

Ready to bet? Get DFO’s latest Conn Smythe odds here!

Visit adjustedhockey.com; data from Hockey-Reference.com