

After examining six long-term NHL contracts that aged wonderfully last week, we’re going to do the inverse today: signings that aged poorly.
Some of these are a byproduct of GMs engaging in egregious July 1 bidding wars. Others aged badly due to unforeseen rapid declines in player production, while some were disasters from the get-go due to GMs overvaluing past performances and ignoring players’ red flags and age. Nothing personal to the players, who got to cash in on big paydays.
Let’s dive right in.
Sept. 13, 2018: Eight years, $78,800,000 ($9.85M cap hit)
Make no mistake — Tyler Seguin was worth every penny of this contract when he signed it.
Back then, Seguin was a bona fide superstar with the Dallas Stars — recording the fifth-most points of any NHL player (464) throughout his first six years in Texas. But not long after securing the bag, Seguin’s game declined due to hip and knee injuries, which caused him to miss all but three games of the 2020-21 season.
He’s been a shell of his former self since. While Seguin’s game appeared to head in an upward trajectory last season with 50 points in 76 games, it’ll take an outright miracle for the 31-year-old to regain his stature as a franchise center. It’s a shame, and there’s nobody to blame.
July 1, 2017: Eight years, $56,000,000 ($7M cap hit)
Only the San Jose Sharks know why they gave Marc-Edouard Vlasic an eight-year deal that began when he was 31 years old. Vlasic may have been one of the NHL’s premier shutdown defenders leading up to his big payday, but banking on a player of his ilk maintaining their level of play throughout their 30s is just bonkers.
Sure enough, Vlasic’s game declined drastically once this contract kicked in. Since beginning to carry a $7-million cap hit, the 36-year-old has gone from a sturdy minute-munching top-pairing defender who drives play at all ends of the ice to a third-pairing defenseman whose biggest contribution comes on the penalty kill. Vlasic will occupy about eight percent of San Jose’s cap space for this season.
Dec. 31, 2013: Seven years, $49,000,000 ($7M cap hit)
Dion Phaneuf never lived up to his pedigree with the Toronto Maple Leafs. Following five impressive seasons with the Calgary Flames in his early 20s, Phaneuf’s output fizzled out at both ends of the ice. But alas, the Leafs still deployed him like a No. 1 — for too long — and proceeded to double down on it by making Phaneuf one of the highest-paid defensemen in the NHL.
Throwing a pile of money at Phaneuf didn’t make him miraculously improve. However, Toronto somehow offloaded Phaneuf's contract by trading him to the Ottawa Senators midway through Year 2 of the deal.
Phaneuf’s game improved slightly in Ottawa — albeit never to a point where his deal was anywhere close to digestible — and it earned him a look with the Los Angeles Kings. The Kings bought out the final two years of Phaneuf’s contract after the 2018-19 season.
July 5, 2013: Seven years, $36,750,000 ($5.25M cap hit)
Sorry to add salt to the wound here, Leafs fans. But how could we not talk about David Clarkson in an article like this?
This deal will go down in hockey history as the moment when NHL GMs realized overpaying 28-year-old gritty wingers with one 30-goal season to their name is quite risky.
To put things into perspective, Clarkson’s contract ate up 8.1 percent of Toronto’s cap space, which equates to $6.81M in today’s cap climate. Sure enough, Clarkson regressed to a bottom-six forward in Toronto, and he tallied just 15 goals and 26 points in 118 games with the Leafs before being shipped off to Columbus. Clarkson suited up for just one season in Ohio, during which he was a fourth-line forward. Unfortunately, injuries began to mount around that time, and he was placed on long-term injured reserve.
July 1, 2014: Five years, $27,500,000 ($5.5M cap hit)
Mark the Florida Panthers' signing of Dave Bolland as Exhibit A on why you shouldn’t issue ‘legacy’ contracts. At the time of the signing, Bolland — who scored the game-winning goal in the 2013 Stanley Cup final — was coming off a 12-point campaign in 23 games with the Toronto Maple Leafs.
But Bolland, a gritty second-line forward who thrived in the post-season early in his career, had clout despite his best days being in the rearview mirror. Florida’s GM at the time, Dave Tallon, was a member of the Blackhawks' front office when they drafted him, and he just needed to sign Bolland for five seasons.
A slew of injuries ultimately limited Bolland to just 78 games over two seasons with the Panthers before being shipped off to the Arizona Coyotes — though he never played in a game for the organization.
July 9, 2014: Seven years, $42,000,000 ($6M cap hit)
Nobody batted an eye when the New Jersey Devils made Cory Schneider the eighth-highest-paid goalie in the league.
Schneider had established himself as one of the NHL’s elite netminders in his early 20s. During his first five full NHL seasons, Schneider led all NHL goaltenders — who played at least 100 games — with a .927 save percentage.
While Schneider made his first NHL All-Star Game in Year 1 of the deal in 2015-16, things went south shortly thereafter. Schneider regressed from appearing on the cusp of being a perennial Vezina candidate to a league-average goaltender. Between the 2016-17 and 2019-20 seasons — his final seasons with New Jersey before being bought out — Schneider posted a 46-62-23 record and a .905 save percentage to boot.