Inside The Cubs

Reason Why Cubs' Shohei Ohtani Free Agency Pursuit Failed Finally Revealed

The Chicago Cubs fell out of the Shohei Ohtani free agency sweepstakes because of one mistake.
Grant Young|
Oct 28, 2025; Los Angeles, California, USA; Los Angeles Dodgers two-way player Shohei Ohtani (17) throws to first for an out against Toronto Blue Jays third baseman Addison Barger (47)
Oct 28, 2025; Los Angeles, California, USA; Los Angeles Dodgers two-way player Shohei Ohtani (17) throws to first for an out against Toronto Blue Jays third baseman Addison Barger (47) | Kirby Lee-Imagn Images

In this story:

Chicago CubsLos Angeles Dodgers

The entire baseball community has been captivated by watching Shohei Ohtani compete for the Los Angeles Dodgers in the 2025 MLB World Series.

Then again, the baseball community has been captivated by Ohtani ever since he made his MLB debut in 2018. And since that point, he has gone on to win three MVP awards (with the fourth almost certainly arriving soon because of his success in 2025) while winning a World Series with the Dodgers in 2024.

This attention is owed to Ohtani being a two-way superstar, placing himself among the league's best as both a hitter and a starting pitcher.

There's a case to be made that Ohtani is already the best baseball player of all time. And if someone isn't comfortable making that claim quite yet, they would have to agree that he's at least on track to becoming baseball's GOAT. And given that he signed a 10-year, $700 million contract with the Dodgers in December 2023, there's a very good chance his career ends in Los Angeles.

Los Angeles Dodgers starting pitcher Shohei Ohtani (17) throws during an October 28, 2025 game
Los Angeles Dodgers starting pitcher Shohei Ohtani (17) | Kirby Lee-Imagn Images

Cubs Not Agreeing to Deferred Contract Ruined Shohei Ohtani Free Agency Pursuit

Ohtani's contract with the Dodgers is fascinating because for the first 10 years of his deal, he's only receiving $2 million of the $70 million per year his contract provides. The other $68 million per year is being deferred to be paid out from 2034 to 2043.

This was a revolutionary contract structure that turned the baseball world on its head, and is something the Dodgers have been using ever since with other elite players.

And according to an October 28 article from Jon Heyman of the New York Post, the Chicago Cubs' front office not being willing to do this type of deferred deal is what ended their chances of signing Ohtani when he was a free agent two offseasons ago.

Heyman added that the Cubs "Have no known excuse" for being unwilling to defer a portion of Ohtani's contract, and that this decision "made no sense." However, one would assume that Jed Hoyer and the rest of Chicago's brass probably balked at the idea when it was presented to them because this was unheard of at the time.

The Cubs might be kicking themselves over this mistake right now. That being said, their willingness to deter Ohtani's gigantic contract probably wouldn't have made them a favorite over the Dodgers in signing him. So it's not like Chicago's fan base should feel like this mistake is the reason why Ohtani won't be hitting and pitching at Wrigley Field for the rest of his career.

The Latest Chicago Cubs News

Bryce Harper’s Dog Could Be Cubs’ Secret Weapon Amid Trade Speculation

Luis-Martinez Gomez Emerging As Cubs’ Best Arizona Fall League Pitcher

Cubs Should Lock Down Critical Star This Offseason Before Contract Year Hits

Should Cubs Make Painful Move And Trade Fan Favorite All-Star While Value Is High?

Published
Grant Young
GRANT YOUNG

Grant Young is a Staff Writer for On SI’s Chicago Cubs, New York Mets, Boxing, Indiana Fever, and Women’s Fastbreak sites. Before joining SI in 2024, he wrote for various boxing and sports verticals such as FanBuzz and NY Fights. Young has a bachelor’s degree in marketing and a master’s degree in creative writing with an emphasis on sports nonfiction from the University of San Francisco, where he played five seasons of Division 1 baseball. He fought Muay Thai professionally in Thailand in 2023, loves a good essay, and is driven crazy trying to handle a pitpull puppy named Aura. Young lives in San Diego and was raised in the San Francisco Bay Area.

Home/News