Recalling mistakes from past free agency periods after big salary cap increase

General managers across the NHL are closing in on what could be one of the bigger free agency shopping sprees in recent memory.

With little to no increase in the salary cap, it has been challenging for teams to sign some of the top free agents in recent years. This shouldn’t be surprising, given that the total cap increase has been just $4 million over the past six seasons.

The upper limit of the salary cap is now set to increase to $88 million for the upcoming 2024-25 season, which is a nice $4.5 million bump (5.4 percent increase). The last time we saw an increase like that was back in the 2018-19 season when the salary cap went up from $75 million to $79.5 million ($4.5 million or 6.0 per cent increase).

While this increase should excite hockey fans, who want to see movement around the league, a cautionary tale must be told. Having more cap dollars to spend doesn’t necessarily mean teams will do so wisely.

Granted, no general manager will hit the mark on every free agent signed or trade pulled off, but there are deals they come to regret.

History from past free agency periods where the salary cap experienced a significant increase shows how easy it is to make those mistakes.

Here is a look back at some of the notable ones.

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2018 Free Agency

Salary cap increase: $75 million to $79.5 million (6.0%)

James Neal, Calgary Flames: Five years, $5.75 million AAV

If there was a chance to hit the redo button, the Flames definitely would take a mulligan on singing Neal. Granted, the forward was a consistent 20-goal scorer, but it was also clear that he wasn’t in his prime anymore.

It went so bad in the first year of the deal, where he scored just seven goals in 63 games, that the Flames shipped Neal out of town to the Edmonton Oilers for Milan Lucic. Neal would eventually get bought out, and the Flames had Lucic around for the remainder of his deal, even if he only provided a marginal improvement in production.

Jay Beagle and Antoine Roussel, Vancouver Canucks: Four years, $3 million AAV

If there is a cautionary tale to be told about overpaying for role/depth players, the Canucks signing Beagle and Roussel to identical four-year, $12 million deals tells that story pretty well.

The thought with the deals was to capitalize on the experience both players could provide to a young roster. Unfortunately, it was also a lot of money to pay players who were nothing more than fourth-liners, and while the Canucks had the cap space at the time, those contracts proved to be anchors as the team tried to make improvements.

The duo were part of a big trade with the Arizona Coyotes in an attempt to rid themselves of Loui Eriksson’s contract with Oliver Ekman-Larsson and Conor Garland joining Vancouver. Eventually, Ekman-Larsson had the final four years of his deal bought out by the Canucks and would go on to win a Stanley Cup with the Florida Panthers this season.

Leo Komarov, New York Islanders: Four years, $3 million AAV

A beloved member of the Leafs, Komarov had some interest from a few teams in free agency and decided to join the Islanders. Unfortunately, Komarov saw a diminished role on Long Island and it showed in his production as he scored a total of 11 goals and 48 points in 164 games.

Eventually, the Islanders placed the Russian forward on unconditional waivers to terminate his contract, and Komarov would sign in the KHL with St. Petersburg.

Jack Johnson, Pittsburgh Penguins: Five years, $3.25 million AAV

There were a lot of eyebrows raised when the Penguins offered Johnson a long-term deal, considering he was coming off a season where he scored 11 points in 77 games. He was also looking to get a trade out of Columbus in hopes of getting in a better position ahead of free agency.

There were many warning signs about his play through analytics, but general manager Jim Rutherford was insistent that Johnson was worth the long-term deal. However, head coach Mike Sullivan wasn’t convinced and even made the defender a healthy scratch in the playoffs.

After just two seasons, the Penguins decided to cut their losses and bought out the final three years of Johnson’s contract. Even then, Rutherford would come to defend the defenceman.

“He has never been given a chance here right from the start,” Rutherford said back in 2019. “I don’t understand it. It’s been extremely unfair to him. Extremely. He’s a good player. I think he’s doing fine. I think he’s doing perfectly fine.”

How bad did this deal end up for Pittsburgh? Johnson’s buyout is still on the books for two more seasons at a $916,667 cap hit.

2014 Free Agency 

Salary cap increase: $64.3 million to $69 million (7.31%)

Dave Bolland, Chicago Blackhawks: Five years, $5.5 million AAV

Bolland will always be remembered for his Stanley Cup-clinching goal in 2013 against the Boston Bruins. However, the former Chicago Blackhawks forward didn’t live up to the hype that moment created for him afterwards.

After getting traded to the Toronto Maple Leafs, his hometown team, a lacerated ankle tendon shortened his 2013-14 season to just 23 games. When Toronto decided to let him walk to free agency, Bolland would reunite with former Blackhawks GM Dale Tallon in Florida, but like his tenure in Toronto, he was unable to live up to expectations.

After just 78 games across two seasons with the Panthers, where he contributed just 28 points, Bolland was sent to the AHL. His contract would then get traded to the Arizona Coyotes, and he never played again in the NHL because of a back injury.

Stephane Robidas, Toronto Maple Leafs: Three years, $3 million AAV

Looking to add a stable veteran presence on the blue line, the Leafs went out and signed Robidas. That deal, however, came with some risk as the 37-year-old was coming off a season where he suffered multiple leg fractures.

He would appear in 52 games in his first season with the Leafs, but would never suit up with the team again. The Leafs would quietly place Robidas, Nathan Horton (more on him later) and Joffrey Lupul on long-term injury reserve in order to free up cap space. This would eventually bring up the infamous “Robidas Island” term for teams looking to rid themselves of a deal with a convenient career-ending injury.

This would be something the Leafs would see happen often with other players like Jared Cowen, Jake Muzzin, and now Matt Murray. Other teams would catch on and use LTIR to help navigate the hard salary cap in creative ways.

2013 Free Agency

Salary cap increase: $60 million to $64.3 million (7.17%)

David Clarkson, Toronto Maple Leafs: Seven years, $5.25 million AAV

Coming off their first playoff appearance in nearly a decade that ended in a Game 7 collapse against the Boston Bruins, the Leafs were looking to bolster their lineup. At the start of free agency, they went out and made a splash, signing Clarkson to a seven-year, $36.75-million contract with some dubbing the former New Jersey Devil forward the second coming of Wendel Clark because of his grit and leadership. Plus, he was two seasons removed from scoring 30 goals.

Clarkson’s time with the Leafs couldn’t have started worse. He was suspended for 10 games for leaving the bench to take part in a fight, and it was like the forward had been playing catchup ever since. He was never really able to redeem himself, and it was becoming clear that he would not be able to live up to the expectations placed on him.

The Leafs decided to cut bait with the struggling forward by trading him to the Blue Jackets for Nathan Horton, who was on the shelf with a degenerative back injury and never played another NHL game.

Stephen Weiss, Detroit Red Wings: Five years, $4.9 million AAV

Ken Holland surprised many when he decided to roll the dice on Weiss on a five-year deal after he played just 17 games the year before because of a wrist injury. Clearly, the Red Wings were banking on Weiss bouncing back and producing like he did in the seasons prior.

Unfortunately, Weiss only lasted two seasons in Detroit with injuries and limited production, which forced Holland to buy out the final three years of his deal. That buyout would sit on the Red Wings’ cap for six seasons, but it was seen as a necessary move with the team needing the space for other moves.

Ryane Clowe, New Jersey Devils: Five years, $4.86 million AAV

This contract came with significant risk for the Devils as Clowe had a history of concussions and was coming off a season where he scored just three goals and 19 points in 40 games. It was clear Lou Lamoriello was banking on Clowe bringing his production during his time with the San Jose Sharks, where he had 271 points in 423 games.

Those injury concerns would follow Clowe to New Jersey. After suiting up for 43 games in his first season, he only played 13 games in the second, and doctors advised him not to play again after suffering another concussion, his fourth head injury in about 19 months.

Mike Ribeiro, Arizona Coyotes: Four years, $5.5 million AAV

Ribeiro joined the Coyotes after he produced as a point-per-game player with the Washington Capitals, but that production didn’t follow him. He scored a respectable 47 points in 80 games, although he was a healthy scratch twice.

His tenure in Arizona was shortlived as the Coyotes decided to buy out the final three years of his deal with the team, citing behavioural issues as the reason behind their decision.

Nathan Horton, Columbus Blue Jackets: Seven years, $5.3 million

Horton made it known he had interest in joining the Blue Jackets, and they made a big push for him with a seven-year commitment, but it wasn’t without concerns.

Horton had a tough injury history, including a shoulder injury that required surgery in the off-season, and a history of concussions. Unfortunately, Horton’s tenure only lasted 36 games, and the team was in a tough spot because Columbus didn’t insure his contract.

“With Nathan, there was the possibility we would have been paying him $26 million the next five years to sit in the stands,” general manager Jarmo Kekalainen said at the time. “This is a very important financial decision for us.”

The Blue Jackets would find a way out of that ordeal by trading Horton’s contract to the Leafs for Clarkson although Clarkson’s tenure in Columbus was also plagued by injuries.

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