After Leon Draisaitl signed his massive eight-year extension earlier in the summer, I started thinking about the biggest contracts the Oilers have ever handed out. Over the years, the team has gone from one that couldn’t afford to keep its star players to one that has now handed out a pair of deals worth $100+ million. That’s a sizeable shift for anyone who has been following this team for a long time.
Here’s a list of the five biggest contracts in Oilers’ history, ranked by total value. These deals brought some serious dough to Edmonton, and it’s hard not to think about how each one shaped the team in the salary cap era.
1. Leon Draisaitl – 8 years, $112 million (2025-2033)
Remember when people thought the Oilers paid Draisaitl too much with the $68 million contract they gave him coming out of his ELC? As it turns out, that baby now looks like one of the best contracts in the league, and I’d be willing to bet Gregor’s money that this new contract will look good too. Draisaitl has become an absolute beast for Edmonton, winning a Hart Trophy and lighting up the scoreboard alongside McDavid. At $8.5 million per year for one more season, Leon Draisaitl is a steal for what he brings to the ice—power, skill, and the ability to make goalies sweat on the regular.
2. Connor McDavid – 8 years, $100 million (2018-2026)
Before Leon Draisaitl took over the team lead for total value, Connor McDavid’s $100 million contract was the largest in Oilers history, and let’s be real—he’s worth every penny and more. At $12.5 million per year, Edmonton is getting the best player in the world at a number that seems like a bargain even though he was the highest paid NHLer for years. McDavid is a generational talent who consistently makes defenders look like they’re stuck in quicksand, and I cannot wait to see what he does next. Whether it’s leading the league in points or breaking ankles with ridiculous dangles, Connor McDavid is a stud in every possible way and by this time next year, he’ll be taking over the #1 spot on this list once again.
3. Darnell Nurse – 8 years, $74 million (2021-2029)
After his breakout season in the strange 2020-21 campaign, the Oilers locked up Nurse with a massive $74 million deal after some of his peers locked in around the same value. Without question, this $9.25 million AAV makes some fans more than a little nervous, but the flip side is that we’d all take a 300% increase if our bosses handed it to us too. Either way, when he’s at his best, Nurse is a physical presence on the back end and provides reasonable secondary scoring from the defence. That said, I doubt anyone believes Nurse will ever live up to this contract value, and that’s a shame because there’s no changing it now and the Oilers still need him to perform if they’re going to be successful.
4, 5, and 6. Taylor Hall (2012-2019), Ryan Nugent-Hopkins (2013-2020), and Milan Lucic (2016-2023) – 7 years, $42 million
In a tie for fourth place on the list is a trio of contracts handed out to three very different players. As you know, two of those deals didn’t work out so well for the Oilers while the third player is still here and likely will be forever.
Taylor Hall was supposed to be the cornerstone of Edmonton’s rebuild, and in 2012, the Oilers rewarded him with a seven-year, $42 million contract. At $6 million per year, Hall produced consistently for the Oilers and even went on to win a Hart Trophy—just not in Edmonton. While his contract might not have lived up to the sky-high expectations in the long run, it’s still one of the biggest the Oilers have handed out, and for a few years, Hall was the driving force behind the team.
Nuge might not have the flashiest contract on this list, but the $42 million extension he signed coming out of his ELC was a carbon copy of the Taylor Hall extension signed a year before him. At $6 million per year, the Oilers got a Swiss Army knife who can play centre or wing, kill penalties, work the power play, and generally just do whatever the team needs him to do. He’s a fan favourite for a reason, and it’s interesting to see that the next deal he signed for eight years at $41.5 million was pretty damned close to the last one. Either way, the Oilers are keeping Nuge forever and I couldn’t be happier about it.
Milan Lucic’s $42 million contract might not have aged well, but at the time, the Oilers were looking for a bruising winger to protect McDavid and bring some grit. Unfortunately, Lucic’s production didn’t live up to the price tag, and it led to one of the more infamous buyouts in recent memory. That said, this deal still cracks the list purely because of the size and the expectations that came with it.
There you have it — the six biggest contracts in Oilers history since the salary cap era began. Some paid off in a big way, while others… well, they’re a reminder that not every bet works out.
