The Chicago Cubs signed Jason Heyward to an eight-year, $184 million deal during the 2015-16 offseason. Seven years later, Heyward's contract remains the largest in Cubs history.
During that same offseason, when Heyward signed with the Cubs, left-handed starter David Price received a $217 million deal from the Red Sox, while the Diamondbacks signed right-handed starter Zack Greinke to a $206.5 million deal.
Here are all of the largest contracts in MLB since the 2015-16 offseason, including extensions that are worth more than Heyward's $184 million deal.
2018-19 Largest Contracts
Mike Trout: 10-year, $360 million extension with Angels
Nolan Arenado: 7-year, $234 million extension with Rockies
Bryce Harper: 13-year, $330 million free agent contract with Phillies
Manny Machado: 10-year, $300 million free agent contract with Padres
2019-20 Largest Contracts
Mookie Betts: 12-year, $365 million extension with Dodgers
Christian Yelich: 7-year, $188 million extension with Brewers
Gerrit Cole: 9 year, $324 million free agent contract with Yankees
Stephen Strasburg: 7-year, $245 million free agent contract with Nationals
Anthony Rendon: 7-year, $245 million free agent contract with Angels
2020-21 Largest Contracts
Francisco Lindor: 10-year, $341 million extension with Mets
Fernando Tatis Jr.: 14-year, $340 million extension with Padres
2021-22 Largest Contracts
Austin Riley: 10-year, $212 million extension with Braves
Corey Seager: 10-year, $325 million free agent contract with Rangers
2022 Largest Free Agent Contracts (So Far)
Aaron Judge: 9-year, $360 million free agent contract with Yankees
Carlos Correa: 13-year, $350 million free agent contract with Giants
Trea Turner: 11-year, $300 million free agent contract with Phillies
Xander Bogaerts: 11-year, $280 million free agent contract with Padres
Jacob deGrom: 5-year, $185 million free agent contract with Rangers
So, not including the two bigger deals during the same offseason when Heyward signed, there have been 18 larger contracts than the Cubs have ever agreed to.
Adapt or die? The Cubs have the shovel and are digging their own grave.
But we know there have been bigger deals (one player the same) even before Heyward was signed and once again it shows the Cubs ineptitude when it comes to trying to go after or trying to keep the best players.
Largest Extensions Prior to 2015
Giancarlo Stanton: 13-year, $325 million extension with Marlins (2014)
Miguel Cabrera: 8-year, $248 million extension with Tigers (2014)
Joey Votto: 10-year, $225 million extension with Reds (2012)
Clayton Kershaw: 7-year, $215 million extension with Dodgers (2014)
Derek Jeter: 10-year, $189 million extension with Yankees (2001)
Joe Mauer: 8-year, $184 million extension with Twins (2010)
Largest Free Agent Contracts in MLB Prior to 2015
Alex Rodriguez: 10-year, $275 million free agent contract with Yankees (2008 after opting out)
Alex Rodriguez: 10-year, $252 million free agent contract with Rangers (2001)
Robinson Cano: 10-year, $240 million free agent contract with Mariners (2014)
Albert Pujols: 10-year, $240 million free agent contract with Angels (2012)
Prince Fielder: 10-year, $214 million free agent contract with Tigers (2012)
That is 11 more deals bigger than anything the Cubs have ever given a player. Overall, almost two-thirds of the teams in MLB have signed a player to a larger contract than the Cubs.
And yes, you're right. Some of these deals have been absolute disasters. But that doesn't mean you stop trying. You cannot tell me with a straight face that you wouldn't want Manny Machado or Bryce Harper on the Cubs right now. Or Aaron Judge. Or pick another star free agent that's gone somewhere else in recent years.
You want the best players? Pay them.
I wrote more about the current state of the Cubs after seemingly choosing to pass on Correa this offseason.
More on the Cubs on the Pinwheels And Ivy Podcast tonight at 8 p.m. CST.
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