Biggest trades in NHL history

San Jose Sharks acquire Date Ottawa Senators acquire
Erik Karlsson
Francis Perron
September 13, 2018
Josh Norris
Chris Tierney
Rudolfs Balcers
Dylan DeMelo
2019 2nd round pick
2019 or 2020 conditional 1st round pick
2021 conditional 1st or 2nd round pick
2022 conditional 1st round pick
Comment: The 2019 2nd rounder is the better of San Jose's own or Florida's own, previously acquired. If the Sharks miss the playoffs in 2018-19, the 2019 or 2020 first-rounder will be in 2019; otherwise, it’s a 2020 first-round pick that will go to Ottawa. If the Sharks re-sign Karlsson the Senators receive a conditional second-round pick in 2021 which would become a first-round pick if the Sharks make it to the Stanley Cup Final in 2019. If Karlsson is on an Eastern Conference roster (reserve list during the 2018-19 season, the Sharks would have to send the Senators an additional first-round pick no later than 2022.
St. Louis Blues acquire Date Buffalo Sabres acquire
Ryan O`Reilly
July 1, 2018
Vladimir Sobotka
Patrik Berglund
Tage Thompson
2019 1st round pick
2021 2nd round pick
Tampa Bay Lightning acquire Date New York Rangers acquire
Ryan McDonagh
J.T. Miller
February 26, 2018
Vladislav Namestnikov
Libor Hajek
Brett Howden
2018 1st round pick
2019 conditional 2nd round pick
Comment: Conditional 2nd round pick becomes a first-rounder if the Lightning win the Stanley Cup in either 2018 or 2019.
Ottawa Senators acquire Date Colorado Avalanche acquire
Matt Duchene
November 5, 2017
Shane Bowers
Andrew Hammond
2018 1st round pick
2018 3rd round pick
Comment: 3-team trade between Senators, Avalanche and Predators
Nashville Predators acquire Date Colorado Avalanche acquire
Kyle Turris
November 5, 2017
Samuel Girard
Vladislav Kamenev
2018 2nd round pick
Comment: 3-team trade between Senators, Avalanche and Predators
Montreal Canadiens acquire Date Nashville Predators acquire
Shea Weber
June 29, 2016
PK Subban
New Jersey Devils acquire Date Edmonton Oilers acquire
Taylor Hall
June 29, 2016
Adam Larsson
Nashville Predators acquire Date Columbus Blue Jackets acquire
Ryan Johansen
January 6, 2016
Seth Jones
Pittsburgh Penguins acquire Date Toronto Maple Leafs acquire
Phil Kessel
Tim Erixon
Tyler Biggs
2016 conditional 2nd round pick
July 1, 2015
Kasperi Kapanen
Scott Harrington
Nick Spaling
2016 conditional 1st round pick
2016 3rd round pick
Los Angeles Kings acquire Date Boston Bruins acquire
Milan Lucic
June 26, 2015
Martin Jones
Colin Miller
2015 1st round pick
Calgary Flames acquire Date Boston Bruins acquire
Dougie Hamilton
June 26, 2015
2015 1st round pick
2015 2nd round pick
2015 2nd round pick
New York Rangers acquire Date Arizona Coyotes acquire
Keith Yandle
Chris Summers
2015 4th round pick
March 1, 2015
Anthony Duclair
John Moore
2015 2nd round pick
2016 1st round pick
Buffalo Sabres acquire Date Winnipeg Jets acquire
Jason Kasdorf
Zach Bogosian
Evander Kane
February 11, 2015
Brendan Lemieux
Joel Armia
Drew Stafford
Tyler Myers
2015 1st round pick
Dallas Stars acquire Date Ottawa Senators acquire
Jason Spezza
Ludwig Karlsson
July 1, 2014
Alex Chiasson
Alexander Guptill
Nicholas Paul
2015 2nd round pick
Anaheim Ducks acquire Date Vancouver Canucks acquire
2015 3rd round pick
Ryan Kesler
June 27, 2014
2014 1st round pick
Luca Sbisa
Nick Bonino
2014 3rd round pick
New York Rangers acquire Date Tampa Bay Lightning acquire
Martin St. Louis
March 5, 2014
2014 conditional 2nd round pick
2015 1st round pick
Ryan Callahan
Comment: Should the Rangers advance to the 2014 Eastern Conference Final, the 2014 second-rounder would become a first-round pick. In the event Callahan should re-sign with the Lightning, the Rangers would receive Tampa Bay`s second-round pick at the 2015 NHL Draft while the Lightning would receive the Rangers` seventh-round draft pick in 2015.
St. Louis Blues acquire Date Buffalo Sabres acquire
Ryan Miller
Steve Ott
February 28, 2014
Jaroslav Halak
Chris Stewart
William Carrier
2015 1st round pick
2016 3rd round pick
New York Islanders acquire Date Buffalo Sabres acquire
Thomas Vanek
October 27, 2013
2014 1st round pick
Matt Moulson
2015 2nd round pick
Boston Bruins acquire Date Dallas Stars acquire
Loui Eriksson
Joe Morrow
Reilly Smith
Matt Fraser
July 4, 2013
Tyler Seguin
Rich Peverley
Ryan Button
Vancouver Canucks acquire Date Florida Panthers acquire
Lukas Krajicek
Roberto Luongo
2006 6th round pick (#163-Sergei Shirokov)
June 23, 2006
Bryan Allen
Alex Auld
Todd Bertuzzi
2007 conditional 6th round pick (not exercised)