Sometimes, they're game-changers.

When a team makes a bid for an unrestricted free agent and it works out, everyone's happy.

Jerseys start selling. Wins start coming. And Stanley Cup parades seem possible.

But when those free-agency gambles don't pay off…ouch.

Losses pile up. Coaches get fired. And general managers start cleaning out desks, too.

Each of the NHL's 31 veteran franchises has hit a home run in free agency since the salary cap was installed, and they've each made a faulty bet when it comes to a contract offer, too. In fact, even the soon-to-debut Seattle Kraken wound up with a head-scratcher or two when they dipped into the UFA pool this summer.

This year's highest-profile UFA deal went to defenseman Dougie Hamilton, who took $63 million over seven seasons to ditch the Carolina Hurricanes for the New Jersey Devils.

The B/R hockey writing types looked all the way back to 2005-06 to recall the biggest missteps each organization has made in the cap era—be it a player, a contract term or a total dollar value. Or in many cases, a combination of all three.

Take a look at what we came up with and share a thought or two of your own in the comments.


Anaheim Ducks: Todd Bertuzzi (2007)

The burly winger was a force over several seasons with the Vancouver Canucks, but the Ducks got the post-Steve Moore suspension version. Two years and $8 million wasn't a fortune, but he played just 68 games and scored 14 goals in 2007-08 before Anaheim bought out the deal halfway through. 


Arizona Coyotes: Mike Ribeiro (2013)

Given his status as a point-per-game player with the Washington Capitals, it's not surprising the Coyotes shelled out $22 million over four years for Ribeiro. But to say it didn't work out is an understatement. He slumped to 47 points in 80 games and was bought out after one season, with former general manager Don Maloney saying Ribeiro had "real behavioral issues" during his time with the franchise.


Boston Bruins: David Backes (2016)

Let the record show that Backes reached 30 goals twice and 20 goals four times during his time with the St. Louis Blues, which prompted the Bruins to lavish him with $30 million over five seasons. The production fizzled, however, and the Bruins dealt him to Anaheim after 39 goals in three-plus seasons.


Buffalo Sabres: Ville Leino (2011)

The summer of 2011 was a challenging one in Buffalo. Just a day after the Sabres dumped $40 million on Christian Ehrhoff, they doled out six years and $27 million to Leino, a 27-year-old winger with 30 NHL goals. Three years later, he'd added just 10 more to that total and was bought out of the deal's back half.


Calgary Flames: Dennis Wideman (2012)

Wideman was a serviceable enough defenseman who'd played parts of seven seasons with four NHL teams, but probably not worth the five years and $26.25 million he was offered by the Flames. He surpassed 22 points just once in the life of the contract and retired after the 2016-17 season.


Carolina Hurricanes: Joni Pitkanen (2008, 2011)

Pitkanen was one of the league's top young defensemen with the Philadelphia Flyers, and the Hurricanes looked to reinvigorate him after a lost season with the Edmonton Oilers. But the three-year, $12 million deal and three-year, $13.5 million extension look bad in retrospect after he reached 40 points just once.


Chicago Blackhawks: Brent Seabrook (2016)

It's good to win Stanley Cups. First, because they're fun. Second, because they help players get paid. Seabrook was one of those players, at age 30, who got an eight-year, $55 million contract in the afterglow of three titles. His performance—go figure—has fallen off, and Chicago shipped him out after the 2020-21 season.