Top 5 Longest NHL Contracts In History

In the NHL, long-term contracts have always been a gamble. Trying to balance financial commitment with the brutal physical toll of the game.

While the league’s salary cap structure discourages lengthy deals today.

There was a time when teams pushed the limits to lock down franchise players for over a decade.

Some gambles paid off. Others became cautionary tales.

In the NHL, long-term contracts are more of a rarity than a norm.

Unlike MLB, where 10+ year deals are almost expected for top-tier talent, hockey’s salary cap structure mixed with the sport’s brutal physical demands makes it difficult to lock in players for the long haul.

But over the years, a few franchises have gone all-in with monster contracts that reshaped not just their rosters, but also how the league regulates long-term financial commitments.

These deals pushed the boundaries of guaranteed money, proration, and even forced the NHL itself to intervene.

1. Ilya Kovalchuk: 17 Years, $102 Million (2010)

When Ilya Kovalchuk signed a 17-year, $102 million deal with the New Jersey Devils, it sent shockwaves across the NHL.

Not just for the number, but for how blatantly the team tried to backload the contract in order to dodge cap penalties.

The league stepped in and voided the contract for salary cap circumvention, marking one of the first times the NHL enforced a cap-related veto.

The Devils later restructured the deal to 15 years and $100M. Still massive, but technically legal under the CBA at the time.

Despite the fireworks, Kovalchuk would later retire early and return to the KHL before making a brief NHL comeback.

This deal sparked stricter CBA language around long-term proration and essentially ended the era of 10+ year mega-deals.

However, players and teams have now been working towards a balance of short terms and higher money, but with the ability to restructure and collect incentives or argue for extensions mid contracts.

2. Rick DiPietro: 15 Years, $67.5 Million (2006)

In what might go down as the boldest (or most reckless) goaltending gamble in modern NHL history.

The New York Islanders handed Rick DiPietro a 15-year deal worth $67.5 million at just 25 years old.

At the time, it was seen as a pioneering move. Locking up a franchise goalie with a flat, predictable base salary.

Unfortunately, DiPietro’s body couldn’t keep up. His career was marred by injuries and surgeries, and he only played 318 games total before the Islanders bought out the remaining years in 2013.

A buyout they’re still paying $1.5 million annually until 2029.

This deal became a cautionary tale about offering lengthy contracts to players in high-risk injury positions and helped normalize front-loaded structures with earlier team outs.

3. Shea Weber: 14 Years, $110 Million (2012)

Originally an offer sheet from the Flyers, Shea Weber’s deal was matched by the Nashville Predators, making it one of the largest defenseman contracts ever signed.

The $110M was heavily front-loaded. Weber earned over $80 million in the first six years via massive signing bonuses, a tactic designed to pressure the Predators into declining to match.

This deal reflected a key change in NHL front office strategy: paying elite players early to reduce long-term risk while still offering them high guaranteed compensation.

Weber never quite finished the contract with Nashville and eventually ended his career on the Arizona Coyotes’ books as a LTIR stash, a common cap loophole in today’s NHL.

4. Alex Ovechkin: 13 Years, $124 Million (2008)

Ovechkin’s deal is the gold standard of high-risk, high-reward long-term contracts. Signed at just 22 years old, Ovi locked in a whopping $124 million over 13 years with no performance incentives, no opt-outs, and no lockout protection.

Just pure base salary dominance. He lived up to every dollar.

Ovechkin has been a franchise cornerstone for the Washington Capitals, bringing them their first Stanley Cup and chasing Wayne Gretzky’s all-time goals record in the process.

This is one of the only supermax-style contracts in NHL history that worked out for both sides.

High-dollar, long-term commitments can work. However most of the time they are reserved for generational talent with bulletproof durability.

Mahomes, Lebron, Messi and any of the other top talent not just in their respective leagues, but active legends of their sports.

5. Zach Parise & Ryan Suter: 13 Years, $98 Million Each (2012)

In 2012, the Minnesota Wild swung for the fences, signing both Parise and Suter to matching 13-year, $98 million contracts.

It was an attempt to fast-track the team into championship relevance, building a dual-core of veteran leadership.

While the Wild became playoff regulars, they never broke through, and the contracts eventually became an anchor.

Both players were bought out in 2021, with the Wild eating nearly $15 million in dead cap space combined per season in 2023 and 2024.

These twin deals represent the dark side of guaranteed longevity. Contracts that keep hurting you even when the players are long gone.

Long-Term Contracts Are Now Dead in the NHL

Since 2013, the NHL’s CBA has capped contracts at 8 years for players re-signing with their team. (7 if signing elsewhere).

The proration rules were tightened, and signing bonus front-loading now triggers stricter scrutiny.

Simply put: the days of 12-to-17 year deals in the National Hockey League (NHL) are done.

Teams now focus on shorter, more flexible extensions that limit cap exposure and allow for earlier roster refreshes.

In today’s league, the structure matters more than the total value.

It’s about cap management, not splash headlines.

The Next NHL Frontier

Long-term deals in the NHL were once seen as the next frontier.

Locking in stars forever, making headlines, and building dynasties. In reality, most of them flamed out due to injuries, cap bloat, or both.

Now, teams play it much smarter: It’s about flexibility, structure, and timing. Not just betting on a player, but making sure the bet won’t haunt you a decade later financially wise.

These contracts didn’t just reshape rosters. They shifted how front offices approach long-term value, risk, and salary cap management.

As the NHL tightened rules around deal length and cap compliance, these mega-contracts became relics of a bolder era.

Still, their legacy lives on in every cautious negotiation and cap-friendly structure we see today.

The NHL learned their lesson and has never looked back.

Next Reads

Credits

Written by: Aidan Anderson
Research and Analysis: Apostle Sports Media LLC
Sources: NHL.com, ESPN, CapFriendly, The Athletic, Sportsnet, TSN, Bleacher Report, The Hockey News, APSM Proprietary Analysis.
Featured Image: Public Domain / Instagram
Disclaimer: This article contains general financial information for educational purposes and does not constitute as professional advice.