The Best (and Worst) Trade Deadline Deals of All Time in the NHL

Phil Kessel

Hockey fans love trades. When the star player changes the team, everybody raises their eyebrows. We can see bombshell trades every year, and the NHL Trade Deadline is one of the most entertaining parts of the season. 

Trade Deadline, by its definition, it's the last day when teams can exchange and trade players between them. Some blockbuster trades usually happen just before the deadline, making it very interesting to follow, and nerve - wrecking for not only the players, but also coaches and general managers. 

Find out the most interesting and important trades in the history of the National Hockey League, that were unexpected blockbusters and, very often, led the team to Stanley Cup glory. 

The Best Trade Deadline Deals in the National Hockey League: 2023-24 Season

One of the biggest moves of 2024 was the trade of Tomáš Hertl. The Czech forward went from the San Jose Sharks to the Vegas Golden Knights. His desire was clear: he wants to play for the Stanley Cup regularly. Similar thoughts were held by Vladimir Tarasenko, who boarded a plane to Florida. And what about Evgeny Kuznetsov? He needed a fresh start, and that's exactly what he got. In the chart below, you can find the best trade deadline deals that happened in the 2023–24 season.

 Name From To
Tomáš Hertl San Jose Sharks Vegas Golden Knights
Matt Dumba Arizona Coyotes Tampa Bay Lightning
Jake Allen Montreal Canadiens New Jersey Devils
Noah Hanifin Calgary Flames Vegas Golden Knights
Vladimir Tarasenko Ottawa Senators Florida Panthers
Erik Johnson Buffalo Sabres Philadelphia Flyers
Jason Zucker Arizona Coyotes Nashville Predators
Pat Maroon Minnesota Wild Boston Bruins
Jake Guentzel Pittsburgh Penguins Carolina Hurricanes
Anthony Duclair San Jose Sharks Tampa Bay Lightning
Evgeny Kuznetsov Washington Capitals Carolina Hurricanes
Evgeny Kuznetsov

The Best and Worst Trade Deadline Deals

It's difficult to create a ranking of the best and worst trade deadline deals in NHL history. However, there are some aspects that can show if a specific trade was successful or if it was a total bust. For example, Kevin Shattenkirk's move from the Blues to the Capitals was simply horrible. One of the best defensemen in the league should have taken Washington's defense to a new level. It didn't go according to plan, and both sides would like to forget, that something like that even happened.

Do you remember how the New York Rangers got stars Vladimir Tarasenko and Patrick Kane before the 2023 NHL playoffs? Well, everybody will remember it, probably forever. One of the favorites to win a Stanley Cup added two superstar players, but to no effect. It was a gamble, though, an unsuccessful one. Tarasenko then left for the Senators and Kane took a break and joined the Red Wings. 

Justin Schulz

We should also mention Mattias Ekholm's move from the Nashville Predators to the Edmonton Oilers for Tyson Barrie and two draft picks, including their first-rounder. Was it worth it? Absolutely not. Often, the worst deals for one team are the best for the other.

For example, when the Kings got Marián Gáborík in 2014, it was a huge step in the hunt for the Stanley Cup. What about Justin Schulz's trade from the Edmonton Oilers to the Pittsburgh Penguins? The forward won two cups with the Pens putting up 17 points in 36 playoff games. You can also get a captain, who could eventually lead you to the Stanley Cup. As the Vegas Golden Knights will tell you when they got Mark Stone from the Ottawa Senators along with Tobias Lindberg for a package that included Erik Brannstrom, Oscar Lindberg, and a 2020 draft pick. 

The Best Trade Deadline Deals: Last Decade in the NHL 

Sometimes a fresh start is what some players need. For example, Mark Stone was a great player during his time at Ottawa, but when he got traded to Las Vegas, he became a superstar (and also the first captain in the history of the Golden Knights). Brandon Montour for the Buffalo Sabres was good, but for the Florida Panthers? He is terrific. We can also chat about Phil Kessel, a three-time Stanley Cup champion, whose move from the Toronto Maple Leafs fueled his playoff hopes.

 Name From To Year
Eric Staal Carolina Hurricanes New York Rangers 2016
Kimmo Timonen Philadelphia Flyers Chicago Blackhawks 2015
Jaromír Jágr New Jersey Devils New York Rangers 2015
Brandon Montour Buffalo Sabres Florida Panthers 2019
Jeff Petry Edmonton Oilers Montreal Canadiens 2015
Mark Stone Ottawa Senators Vegas Golden Knights 2019
Ryan McDonagh New York Rangers Tampa Bay Lightning 2018
Phil Kessel Toronto Maple Leafs Pittsburgh Penguins 2015
Mark Stone

The Best Trade Deadline Deals: All Time in the NHL 

Legends cannot be traded? It's not the way it works. Everybody can be traded, and superstar players like Dominik Hašek, Rob Blake, Patrick Roy, Jerome Iginla, Ron Francis, or Roberto Luongo will agree. These are the some of the most mind-blowing NHL trade deadline moves of all time:

 Name From To Year
Rob Blake Los Angeles Kings Colorado Avalanche 2001
Jeff Carter Columbus Blue Jackets Los Angeles Kings 2012
Dominik Hašek Buffalo Sabres Detroit Red Wings 2001
Marián Hossa Atlanta Trashers Pittsburgh Penguins 2008
Brendan Shanahan Hartford Whalers Detroit Red Wings 1996
Jerome Iginla Calgary Flames Pittsburgh Penguins 2013
Butch Goring Los Angeles Kings New York Islanders 1980
Marián Gáborík Columbus Blue Jackets Los Angeles Kings 2014
Chris Pronger Edmonton Oilers Anaheim Ducks 2006
Patrick Roy Montreal Canadiens Colorado Avalanche 1992
Roberto Luongo Vancouver Canucks Florida Panthers 2014
Ron Francis Harford Whalers Pittsburgh Penguins 1991
Marián Gáborík

Trades are an essential part of the NHL. Sometimes they can change the whole perspective of the team's season and bring success. However, there are times when teams find out that they just traded away a future star. In many ways, it's a big gamble. General managers can show their abilities and strategic thinking. But don't forget one of the most important mantras of trades at the deadline: timing is everything.

 Photo Source: RMNB, Bleacher Report, NBC Sports 
Jakub Vaverka

Jakub Vaverka

I create content for social media for a living and I live hockey. Going to NHL games and writing blogs about my most favorite game is a dream come true.


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