Ek’s TOP 12 Early-Season Trades in the 21st Century

The Rumer Mill is rather quiet right now, which is normal for this part of the early season in the NHL.  Teams are still evaluating… there’s a ton of parity…etc  

But keep the faith Hockey Buzzards! We’re about a week away from when things really start picking up right around here..Thanksgiving in America.. (You Canadians, I know you guys thanked everybody a month ago….always have to be more polite, don’t you??)

Anyway, I have kept crazy amounts of notes over the years about my discussions with everybody, as well as trends and what’s happening, and I thought it would be interesting to go through everything  and organize my notes by month…I’ve come up with some really interesting tidbits about early season trades and their history over the last 25 years…. The trends, what kind of trades happen, what teams are likely to pull the trigger earlier than later….etc…

Today, I thought it would be interesting to look at the 12 most impactful trades that have happened in the early trade season….You all know me and my rankings… so I decided to come up with  a ranking system that would rate the 12 Biggest trades that have happened in November, December, and January since I’ve been doing this…

My Ranking was based on these parameters.

Player QualityImpactShock ValueTiming:Historical significance

First a quick overview of the three months and how things have changed since the salary cap era….

November is the quietest month, averaging just 3-6 trades per seasonDecember shows moderate activity with 8-12 trades per seasonJanuary is the most active early-season month with 10-15 trades per seasonCombined, these three months account for 21-33 trades annually (25-30% of yearly total)The salary cap era (2005-present) fundamentally changed early-season trading patternsRecent years (2020-2025) show increasing willingness to make early-season blockbusters

Let’s get into this….

The Top 12 Early Season Trades  In the 21st Century

12. Mackenzie Blackwood (SJS → COL) – December 9, 2024

Avalanche receive: Mackenzie Blackwood, Givani Smith, draft pickSharks receive: Alexandar Georgiev, Nikolai Kovalenko, two picks

Impact Score: 8/10 Shock Value: 5/10

Ek: this was the beginning of Colorado fixing their goaltending. Blackwood has been solid and has been considered now for the Olympic team.

11. Erik Karlsson (OTT → SJS) – September 13, 2018

Senators receive: Chris Tierney, Dylan DeMelo, Rudolfs Balcers, Josh Norris, 1st round pick, 2nd round pickSharks receive: Erik Karlsson, Francis Perron

Impact Score: 8/10 Shock Value: 7/10

Ek: I know it’s September but I wanted to include this trade because it was such a major deal at the time. Also, that first round draft pick became.Tim Stutzle for Ottawa….

10. Cam Fowler (ANA → STL) – December 14, 2024

Blues receive: Cam Fowler, 2027 4th round pickDucks receive: Jeremie Biakabutuka, 2027 2nd round pick

Impact Score: 5/10 Shock Value: 6/10

Ek: December 2024 was a BIG trade month. 

9. Ilya Kovalchuk (ATL → NJD) – February 4, 2010

Thrashers receive: Johnny Oduya, Niclas Bergfors, Patrice Cormier, 1st round pick, 2nd round pickDevils receive: Ilya Kovalchuk, Anssi Salmela, 2nd round pick

Impact Score: 7/10 Shock Value: 5/10

Ek: technically, February, but very early February so I’m gonna count it because it was such an important trade at the time and the terms of Kovalchek’s  contract in New Jersey had a major impact on the way contracts could be….

8. Kaapo Kakko (NYR → SEA) – December 18, 2024

Rangers receive: Will Borgen, 2025 3rd round pick, 2025 6th round pickKraken receive: Kaapo Kakko, 4th round pick

Impact Score: 5/10 Shock Value: 8/10

Ek: Less than 24 hours after Kakko complained about being a healthy scratch, the Rangers traded the 2019 No. 2 overall.  I found people outside of New York saying this was a shocking move, but Ranger fan seemed to feel like it was coming all along

7. Jacob Trouba (NYR → ANA) – December 6, 2024

Rangers receive: Urho Vaakanainen, 2025 4th round pickDucks receive: Jacob Trouba (captain)

Impact Score: 6/10 Shock Value: 9/10

Ek: team captains are not traded during the season. Very very rare. And the fact that Anaheim took on the entire $8 million cap hit was also rare. The Rangers made this trade and the Kakko trade just 12 days apart.

6. Taylor Hall (NJD → ARI) – December 16, 2019

Devils receive: Nick Merkley, Nate Schnarr, Kevin Bahl, conditional picksCoyotes receive: Taylor Hall

Impact Score: 7/10 Shock Value: 8/10

Ek: A former MVP traded in mid-December.

5. Jack Eichel (BUF → VGK) – November 4, 2021

Sabres receive: Alex Tuch, Peyton Krebs, 1st round pick, 2nd round pickGolden Knights receive: Jack Eichel, 3rd round pick

Impact Score: 8/10 Shock Value: 7/10

Ek: we will never know what would’ve happened if the Sabres had let him have the operation he wanted to.. this might be called the biggest blockbuster earliest in the actual season ever….

4. Jaromir Jagr (WSH → NYR) – January 23, 2004

Capitals receive: Anson CarterRangers receive: Jaromir Jagr 

Impact Score: 8/10 Shock Value: 7/10

Ek: the interesting thing about this…and I had forgotten this….Jagr was the highest paid player in the NHL at the time.  The Capitals just couldn’t afford him.

3. Mikko Rantanen (COL → CAR) – January 24, 2025

Avalanche receive: Martin Necas, Jack Drury, draft picksHurricanes receive: Mikko Rantanen, Taylor Hall (via Chicago)Blackhawks receive: draft picks, retained salary

Impact Score: 9/10 Shock Value: 8/10

Ek: last year’s very shocking trade. this turned into an absolute mess for Carolina…. Still baffled how Colorado didn’t manage to keep him.

2 . Matthew Tkachuk (CGY → FLA) – July 23, 2022

Flames receive: Jonathan Huberdeau, MacKenzie Weegar, Cole Schwindt, 1st round pickPanthers receive: Matthew Tkachuk, 4th round pick

Impact Score: 10/10 Shock Value: 10/10

Ek: OK, yes this was July. But still technically an early season trade and a trade that happened out of nowhere for many people.   One of those trades that you remember where you were when it happened…and has led to two Stanley Cups.

1. Joe Thornton (BOS → SJS) – November 30, 2005

Bruins receive: Wayne Primeau, Marco Sturm, Brad StuartSharks receive: Joe Thornton

Impact Score: 10/10 Shock Value: 10/10

Ek:  I know people who consider this the first blockbuster deal of the modern era.  And with good reason.  This trade stands alone in NHL history as the only time a player was traded in the middle of an MVP season. Thornton was leading the league in scoring when Boston dealt him.  He didn’t play physical enough for the BOSTON fan base and team elders… Thornton was a big player who played on the perimeter, but was one of the best playmaker of all time.  The Bruins wanted them to go to the net and use hissize….The move redefined the San Jose Sharks for 15 years.  

So that’s my list.  Let me know what you think and I’m off to the phones to try to find the next great early season trade!