Cubs' aversion to long-term, big-money contracts really isn't anything new

One measure has Chicago as a solidly middle-of-the-pack team when it comes to big contracts.

Chicago Cubs Introduce Dansby Swanson
Chicago Cubs Introduce Dansby Swanson | Michael Reaves/GettyImages

The Chicago Cubs know their comfort zone when it comes to free agents and rarely step outside it. This winter is no exception, with Jed Hoyer altogether sitting out the bidding for the winter's top two prizes in Juan Soto and Corbin Burnes.

We've made a lot of the Cubs' aversion to spending at the top of the market lately. It's hard not to, coming off another 83-win season that started with so much promise and excitement after luring Craig Counsell away from the NL Central rival Brewers last fall. But this tweet makes it clear: this approach is nothing new for the franchise.

The Cubs have five $100+ million contracts in their history. Fewer than the Texas Rangers, Washington Nationals, Colorado Rockies and Seattle Mariners. That doesn't feel great. Then you look at some of the other big-market teams here: Boston has 10, the Dodgers have 12, the Mets have 9, the Yankees have 11 - they're just dwarfing Chicago.

The five men to eclipse $100 million with the Cubs?

  • Jason Heyward: $184 million (eight years)
  • Dansby Swanson: $177 million (seven years)
  • Jon Lester: $155 million (six years)
  • Alfonso Soriano: $136 million (eight years)
  • Yu Darvish: $126 million (six years)

Four of the five have come since the Ricketts family purchased the team in 2009. The only one that came prior was the eight-year, $136 million deal Alfonso Soriano signed ahead of the 2007 campaign. That first year in Chicago was hands-down his best in a Cubs uniform. He was solid the rest of the way, averaging 2.1 fWAR annually from 2008-2012, but never came close to replicating that 6.7 fWAR season from 2007.

Cubs have signed four $100+ million contracts in the last decade

The Jon Lester signing, which came ahead of the 2015 season, was a bold proclamation to the rest of the league that the Cubs were ready to aim for a title. That year, Lester spearheaded the rotation alongside Jon Lester as the Joe Maddon-led group made a surprise run to the NLCS.

He was joined by Jason Heyward the following offseason, with the outfielder coming off a stellar walk year in St. Louis. The deal, even with the infamous rain delay speech in Game 7, is widely considered a major bust. Over the course of the contract, he was worth just 7.1 fWAR in a Cubs uniform - hardly what was expected from the recipient of the largest deal in Cubs history.

Yu Darvish got off to a rocky start, but closed his brief Cubs tenure with a flourish - with a second-place finish in NL Cy Young voting in the shortened 2020 season. The team shipped him to San Diego that winter as part of a series of cost-cutting moves brought on by the pandemic.

Most recently, Dansby Swanson inked a mega-deal with the Cubs: a seven-year, $177 million contract that runs through the 2029 season. Through the first two years of the deal, the Gold Glove shortstop has accumulated 9.2 fWAR - but Chicago is yet to taste postseason baseball with Swanson in tow.

This trip down memory lane just goes to show that, yes, the Cubs will open up the pocketbook (to an extent) for the right player. But blowing free agents out of the water with record-setting deals is something they've never done. Should they? Yes. Could they? Yes. But this has long been the norm in Wrigleyville - and I'm honestly not sure what it would take to change it at this point.

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