Today is the NHL’s trade deadline day.
Which NHL GM will win the 2026 NHL Trade Deadline Buffoon of Buffoons Award?
Every year at the NHL trade deadline, contenders convince themselves that one more piece will deliver the Stanley Cup. Sometimes they’re right.
But just as often, the pressure of the moment leads to overpayments, panic moves, or franchise-altering mistakes.
Looking back through NHL history, several deadline deals stand out not because they helped a playoff run—but because they became cautionary tales.
Here are ten of the worst.
- Washington trades Filip Forsberg to Nashville (2013)
Capitals receive: Martin Erat, Michael Latta
Predators receive: Filip Forsberg
This might be one of the worst deadline deals of the modern era.
Washington traded Forsberg before he even played an NHL game. The young Swede became a franchise cornerstone in Nashville, developing into a perennial 30-goal scorer and one of the league’s best wingers.
Meanwhile, Erat lasted barely a season in Washington.
- Penguins acquire Marian Hossa for a Cup run (2008)
Penguins receive: Marian Hossa, Pascal Dupuis
Thrashers receive: Colby Armstrong, Erik Christensen, Angelo Esposito, 2008 1st-round pick
Pittsburgh made one of the biggest deadline splashes in years when they acquired superstar winger Marian Hossa.
The Penguins reached the Stanley Cup Final — but lost to Detroit.
Then came the twist.
That summer Hossa signed with the Red Wings, the very team that had just beaten Pittsburgh in the Final.
- Buffalo trades a 1st-round pick for Steve Bernier (2008)
Sabres receive: Steve Bernier
Sharks receive: 2008 1st-round pick
Buffalo believed Bernier might become a power forward who could help push them into the playoffs.
Instead they traded a first-round pick for a player who produced just 1 goal and 4 points in 17 games after the deadline.
The Sabres missed the playoffs anyway.
San Jose used the pick to draft Charlie Coyle, who went on to carve out a long and productive NHL career.
In deadline terms, this one checked every box: panic trade, rental player, and a lost first-round pick.
- Sharks trade Josh Gorges and a 1st-round pick for Craig Rivet (2007)
Sharks receive: Craig Rivet
Canadiens receive: Josh Gorges, 2007 1st-round pick
San Jose wanted veteran defensive help for the playoffs.
Instead, they gave Montreal a first-round pick and a reliable long-term defenseman for a short-term rental who played only 30 games for them that season.
Classic rental overpayment.
- Flames trade Jarome Iginla to Pittsburgh (2013)
Flames receive: Kenny Agostino, Ben Hanowski, 1st-round pick
Penguins receive: Jarome Iginla
This deal looked reasonable at the time, but the return never delivered.
Neither prospect became a significant NHL player, and the first-round pick turned into Morgan Klimchuk, who played just one NHL game.
Calgary fans are still wondering what might have been if the team waited for a better offer.
- Toronto trades Tuukka Rask to Boston (2006)
Leafs receive: Andrew Raycroft
Bruins receive: Tuukka Rask
Toronto wanted immediate goaltending help.
Boston got a future Vezina Trophy winner.
Raycroft lasted two seasons in Toronto, while Rask became a franchise legend for the Bruins.
- Canadiens trade Ryan McDonagh to the Rangers (2009)
Canadiens receive: Scott Gomez
Rangers receive: Ryan McDonagh, Chris Higgins, Pavel Valentenko
Montreal thought they were acquiring a star center.
Instead they gave away a future No.1 defenseman while absorbing Gomez’s massive contract.
It haunted the Canadiens for years.
- Oilers trade the pick that became Mathew Barzal (2015)
Oilers receive: Griffin Reinhart
Islanders receive: 16th & 33rd picks (Barzal + Anthony Beauvillier)
Edmonton traded two premium draft picks for a struggling defenseman who played just 29 games for the organization.
Barzal went on to win the Calder Trophy.
- Sharks trade for Erik Karlsson (2018)
Sharks receive: Erik Karlsson
Senators receive: Chris Tierney, Dylan DeMelo, Josh Norris, Rudolfs Balcers, picks
Karlsson was spectacular—but the trade gutted San Jose’s future.
Josh Norris developed into a top scorer for Ottawa, and the Sharks eventually sank into a long rebuild.
- Vancouver trades Cam Neely to Boston (1986)
Canucks receive: Barry Pederson
Bruins receive: Cam Neely, 1st-round pick
Boston received a Hall-of-Fame power forward who became the face of the franchise.
Vancouver got two mediocre seasons from Pederson.
Former NHL GM Brian Burke is frequently quoted as saying that more mistakes are made by NHL general managers on trade deadline day than on any other day of the year.
Will a new addition to the list emerge sometime today before the 3 pm deadline?
Count on it.
