Wayne Gretzky and Mark Messier, Mario Lemieux and Jaromir Jagr, Sidney Crosby and Evgeni Malkin. We’ve seen plenty of dynamic duos throughout the history of the NHL. The best of the best rack up regular-season points and trophies with ease, but what makes them truly special are Stanley Cups. Connor McDavid and Leon Draisaitl more than belong in this legendary group; however, the most important trophy of all continues to elude them in cruel fashion.
There’s nothing quite like having a two-headed monster in hockey. Not just one, but two all-world superstar talents on the same team, creating almost an unstoppable force for opponents to handle. There haven’t been many in the history of the game, certainly not to this level. Funny enough, the Edmonton Oilers and Pittsburgh Penguins have been spoiled with two lengthy eras of it.
From 1979-1980 until 1987-88, the Oilers iced the duo of Wayne Gretzky and Mark Messier. The greatest player of all time and another all-time great tormenting the NHL for nine years. The end result was a boatload of points and a full trophy case: 4 Stanley Cups, 3 Conn Smythe Trophies, 7 Art Ross Trophies, 8 Hart Trophies, and 5 Ted Lindsay Awards. Could there have been a better way for the Edmonton Oilers to debut and emerge as a mainstay NHL franchise?
Just as Gretzky’s days as an Oiler were ending, came the next dynamic duo that was arguably the best we’ve ever seen. Mario Lemieux and Jaromir Jagr were drafted six years apart by the Pittsburgh Penguins, a franchise in disarray before their arrival.
Lemieux exploded onto the scene immediately to begin his NHL career, but not until Jagr joined him did team success follow. Lemieux and Jagr led the Penguins to back-to-back Stanley Cups in their first two years together. On top of that, their tenure saw 2 Conn Smythe Trophies, 11 Art Ross Trophies, 3 Hart Trophies, and 4 Ted Lindsay Awards. The most unfortunate part of all was that Lemieux missed a large chunk of time in the late 90s for various reasons, including a battle with cancer and serious injuries, which then forced him to come in and out of retirement. It’s wild to imagine how much more individual and team hardware these two could have captured as a duo.
As Lemieux’s career dwindled down and Jagr was dealt out of town, the Penguins found themselves back where they were 20 years prior. Things were not looking good until another young Canadian and a young European showed up and took over. Evgeni Malkin in 2004, followed by Sidney Crosby in 2005. Just like Mario and Jagr, it didn’t take too long for Sid and Geno to put Pittsburgh back on the map in the hockey world.
They suffered heartbreak in the Stanley Cup Finals during just their third season as partners in crime, but that only fueled them moving forward. 3 Stanley Cups in the eight years to follow, including another back-to-back celebration in the Steel City in 2015-16 and 2016-17. Both dealt with injuries and highs and lows along the way, but that wasn’t even close to enough to keep them empty-handed. 3 Conn Smythe Trophies, 4 Art Ross Trophies, 3 Hart Trophies, and 4 Ted Lindsay Awards, all in a time when scoring was down across the league.
As Crosby and Malkin were in the midst of winning their back-to-back Stanley Cups, Connor McDavid was introducing himself to the NHL as a teenager, looking like the next all-time great in the making. He idolized Sidney Crosby growing up, and oh boy, does he possess many of the same great characteristics as Sid the Kid.
The hockey world knew McDavid was special before he even stepped foot in the pros. For Leon Draisaitl, it wasn’t as sure a thing, and he took several years to develop. But once he reached his potential, it was over for the rest of the league.
Connor McDavid and Leon Draisaitl’s brilliance
It’s hard to express just how good Connor McDavid and Leon Draisaitl have been as teammates over the last 10 years. The best player in the world by far, and arguably the second-best player in the world, wreaking havoc on the NHL just like those three other duos.
Let’s start with the numbers. A combined 14 100+-point seasons, 6 Art Ross Trophies, 4 Hart Trophies, and 5 Ted Lindsay Awards. There is quite honestly nothing you can do to stop them.
Former NHLer, now ESPN analyst Ray Ferraro has often referred to McDavid as the most technically advanced/evolved hockey player we’ve ever seen, and I 100% agree with him. He does things on the ice that nobody else can do or has done and somehow continues to get better every year. The combination of speed, skill, smarts, and competitiveness results in a guy who may go down as one of the best players of all time, if not the best.
On the other hand, Leon Draisaitl is just a machine. A 6’2″, 209-pound power forward with skill, hockey IQ, and an absolute rocket of a shot. He’s got some Jaromir Jagr and Evgeni Malkin to him, with his own unique touch added on top. Not to mention his ability in the faceoff circle and often unspoken-about defensive play to shut down his opponents.
McDavid and Draisaitl are unbelievable on their own, but what makes them even greater is the chemistry they’ve built through all of these years. How many times has McDavid set up Draisaitl for a one-timer goal? It feels like every other game, 97 finds 29, who then finds the back of the net. They have the sick sense to know where each other is on the ice at all times.
This one from Game 2 of the 2025 finals was just unfair. Another one to add to a laundry list of highlight reel plays from Connor McDavid’s career.
Playoff Journey So Far
When the checking gets tighter, the space is taken away, and the goals are harder to come by, most players’ production goes down. That’s the norm in the Stanley Cup Playoffs; nothing comes easy. But Connor McDavid and Leon Draisaitl are not normal. These two have elevated their play to a different level come the postseason, racking up points at ridiculous rates. They currently stand as the third and fifth all-time points-per-game leaders in Stanley Cup Playoff history.
Despite their individual brilliance, it’s taken some time for team success to follow at the most important time of the year. McDavid and the Oilers made the playoffs just once in his first four seasons, and the two years to follow ended with Edmonton getting bounced in Round 1. This was no fault of McDavid’s or Draisaitl’s, but they knew there was more to give, and from that point forward, they’ve been on a mission.
Trips to the Western Conference Finals, the second round, and then the Stanley Cup Finals were all courtesy of their two-headed monster dragging them as far as humanly possible. Growth was being made, but Edmonton had yet to finish a season as the last team standing. The 2023-24 run felt like the one, McDavid and Draisaitl’s first appearance in the Stanley Cup Finals. But the Florida Panthers came out firing, and the Oilers couldn’t overcome a 3-0 series deficit. They clawed all the way back to force a seventh game just to lose in the most devastating fashion.
There were now two ways it could go after such a crushing loss: did this dynamic duo just miss their best chance to win a cup? Or will this even further motivate two of the all-time greats to reach the summit? One year later, we received our answer loud and clear: the latter.
However… those pesky Florida Panthers once again got in their way. Last year’s loss felt so winnable. The first three games were extremely close affairs that Sergei Bobrovsky helped his team escape victorious. The three Oilers wins to follow were dominant, but we know anything could happen in a Game 7, and it broke the Panthers’ way.
The unfortunate part is that it now feels like a wasted opportunity, because this year, Florida took it to Edmonton. They were in control for most of the series, apart from some big comebacks and overtime heroics. Was Florida even better this year? Or did the Oilers take a step back? McDavid and Draisaitl certainly didn’t.
Edmonton was once again led by its two superstars, bullying their way through the 2025 postseason with the goal of bringing the Stanley Cup back to Canada for the first time in 32 years. They didn’t just win the Western Conference; they dismantled the competition. A 12-4 record saw the Oilers in control from Game 3 of the first round onwards, with the chance to cap it off by getting revenge on the Florida Panthers. But yet again, the Cats were just too much to overcome, and they’ll have the sour taste of a second consecutive year of the ultimate heartbreak in their mouths all summer long.
The Oilers would not have come remotely close to getting this far without the play of the top two leading playoff point scorers. 33 points apiece from McDavid and Draisaitl absolutely lapped the field in another lengthy postseason. Finishing the job would have been the stuff of legends; instead, it feels like another wasted opportunity. It was an impressive run from an Oilers team that looked cooked heading into Round 1, but let’s be honest, this was about 97 and 29. They deserved better.
What the Future Holds
These two have come so close to reaching the top of the mountain. They have to be questioning what it’s going to take to get the job done. You know that back-to-back years of heartbreak will only fuel the two superstars to push through again in the years to come. But that’s easier said than done. The wear and tear of playoff hockey every season is grueling. But with McDavid turning 29 in January and Draisaitl 30 in October, this dynamic duo has at least another 5 years of dominating the sport left in them.
Edmonton should be considered one of the favorites to make it out of the West once again next season. Nobody is more capable of dragging their team to a third consecutive Stanley Cup Finals than McDavid and Draisaitl, especially if Stan Bowman can do some work to provide more help around them.
McDavid and Draisaitl are just like Gretzky-Messier, Lemieux-Jagr, and Crosby-Malkin. All that they’re missing is the ultimate prize, and once they get one, it could be the opening of the floodgates, which could see them creep up to the very top of the all-time duo ranks in hockey history.
While their ceiling in terms of team success remains untapped, the sky is the limit when it comes to individual production. Connor McDavid notably surpassed the 1,000-point milestone early in 2024-25, becoming the fourth-fastest player in NHL history to reach the mark behind only Wayne Gretzky, Mario Lemieux, and Mike Bossy. We see Sidney Crosby continuing to perform as one of the best in the world and racking up numbers at 37 years old. What is stopping McDavid from following in his footsteps?
Wayne Gretzky (2,857 points) is the only player to have reached 2,000 career points in the NHL. Nobody is ever going to come close to passing that record, but if anyone is going to touch up on 2,000, it’s Connor McDavid. 1,082 points in his first 712 games—what makes 918 in his next 712 unreasonable? Nothing. He’s going to do it. Leon knows it, too.
And let’s not forget about Leon Draisaitl, who will hit the 1,000-point mark himself at some point next season. Despite a slow first four NHL seasons (for his standards), the German superstar is already up to 956 points in 790 career games. While Draisaitl is unlikely to reach McDavid levels in terms of points, he’s quietly been working his way up the all-time goal-scoring list.
With 399 tucks to his name, if Leon were to average 40 goals (which might even be low to presume) over the next 8 years, that’s another 320 tallies and 719 overall. That would put Draisaitl among the top 10 all-time in goals, and if my average projection was a little shy, then a leap into the top 4 has the potential to become reality when it’s all said and done.
Long story short, Connor McDavid and Leon Draisaitl are two of the best hockey players that most of us fans will ever watch play, and there truly aren’t two players who are more deserving of winning the Stanley Cup.
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