Breaking down the Cubs’ impending decision on Shota Imanaga’s unique contract

MILWAUKEE, WISCONSIN - OCTOBER 06: Shota Imanaga #18 of the Chicago Cubs pitches during the first inning against the Milwaukee Brewers in game two of the National League Division Series at American Family Field on October 06, 2025 in Milwaukee, Wisconsin.Michael Reaves/Getty

As soon as left-hander Shota Imanaga signed his four-year, $53 million contract with the Cubs before the 2024 season, it was clear his first two years in Major League Baseball were going to be pivotal.

The unique structure gave the Cubs the option after the second or third year to extend the pact to a total of five years and $80 million guaranteed. But if they didn’t, Imanaga could opt out either year and, unless he…