Biggest trades in NHL history

Vegas Golden Knights acquire	Date	Ottawa Senators acquire
Mark Stone	February 25, 2019	Erik Brannstrom Oscar Lindberg 2020 2nd round pick

Columbus Blue Jackets acquire	Date	Ottawa Senators acquire
Matt Duchene Julius Bergman	February 22, 2019	Vitaly Abramov Jonathan Davidsson 2019 1st round pick 2020 conditional 1st round pick
Comment: 2020 pick conditional on Duchene resigning with Colombus, lottery protected if it’s a top 3 pick.

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 conditional 1st round pick 2019 3rd round pick
Comment: 3-team trade between Senators, Avalanche and Predators. If Ottawa’s 2018 1st round pick ends up being a top 10 pick, the Sens have the option to give Colorado their 2019 1st round pick instead.

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