Ranking the 10 best Chicago Cubs moves during the Theo Epstein era

8. Signing Yu Darvish

The Cubs inked Japanese-born starting pitcher Yu Darvish to a six-year deal heading into the 2018 season. It was a big move that was needed to fill Jake Arrieta's rotation spot, which was left vacant when the bearded right-hander left for Philadelphia.

Darvish's time in Chicago did not start well. He only made eight starts before tricep and elbow injuries prematurely ended his 2018 campaign. But things improved in 2019 when Darvish made 31 starts and struck out 229 batters. In the pandemic-shortened 2020 season, Darvish finished 2nd in the National League Cy Young voting and he finally began to look like the frontline starter the Cubs hoped he would be.

Just when Darvish began to find his groove, the Cubs front office turned over from Epstein to his assistant Jed Hoyer. Amidst financial losses from the pandemic and several members of the World Series core reaching the end of their contracts, Hoyer decided to begin a rebuild. The first move in the teardown was trading Darvish, who still had three years of team control left, to the San Diego Padres for a package of prospects that included now top prospect Owen Caissie.

Darvish wasn't able to fully realize his abilities in Chicago, but the trade was a business decision for the team's future. Darvish still speaks glowingly about the franchise and his time with the Cubs resulted in a fascinating domino effect. When the Cubs were courting outfielder Seiya Suzuki, he reportedly spoke with Darvish before making his decision and the pitcher gave a ringing endorsement of the organization. It was a similar story last offseason when Shota Imanaga eventually chose to sign with the Cubs

In many ways, Darvish was the first of a new wave of Japanese stars to come to the United States, and his word carries a lot of weight to players making the jump to MLB. His time with the Cubs has had a lasting impact on the team's ability to attract these potentially game-changing free agents. Suzuki and Imanaga were two of the team's most productive players in 2024 and more free agents are coming. The Cubs are one of the few teams to have a shot at signing Roki Sasaki, a flame-throwing 22-year-old who helped the Japanese team win the World Baseball Classic in 2023. Landing Sasaki is a long shot, but the fact that the Cubs are even involved is more than many other teams can say and you can trace that all the way back to Darvish.