A Look Back at Yu Darvish's Cubs Career As He Contemplates His Future

News came out late last week that former Chicago Cubs ace and current San Diego Padres starter Yu Darvish was considering retirement as he rehabilitates an elbow injury, despite three years remaining on his deal.

Darvish spent three seasons with the Cubs before eventually being traded to the Padres prior to the 2021 season. Over three seasons, Darvish appeared in only 51 games for Chicago, as his playing time was cut short by injuries and the shortened 2020 season.

After appearing in only eight games for Chicago in 2018, Darvish posted a solid campaign in 2019, finishing the year with a 6-8 record, a 3.98 ERA and a league-leading 33 home runs allowed. Despite allowing so many home runs, Darvish still recorded 178 innings and an impressive tally of 229 strikeouts.

The Japanese international followed it up with a strong 2020 season where he finished second in Cy Young Award voting after posting an 8-3 record (led the league in wins) to go along with a 2.01 ERA and 93 strikeouts.

A trade to San Diego followed in the offseason of 2020, where Darvish spent his last five years. Three of which were remaining on his free agent contract signed with Chicago and the other two were added on via an extension.

Chicago was able to net quite a return for Darvish, but how has the trade panned out today?

How the trade has panned out for San Diego

Originally, it felt like Chicago could’ve gotten a steal for Darvish. However, it hasn’t really turned out that way. The Cubs sent Darvish and catcher Victor Caratini to San Diego in exchange for Zach Davies and four other prospects. As of right now, the Padres have gotten the better of that trade.

Of Darvish’s three remaining years on his contract in San Diego, he posted 6.9 WAR, most of which (4.6) came from a stellar 2022 season where he went 16-8 with a 3.01 ERA. As for Caratini, he only spent one season with the Padres. In that campaign, he posted zero WAR in 116 games.

Grading Chicago’s haul for Darvish

Although Darvish and Caratini only combined for 6.9 WAR in four seasons, the Cubs haul has done far worse. For starters, Zach Davies pitched one season for Chicago and accumulated -1.0 WAR after leading the league in walks and posting a 5.78 ERA in 2021. One of the prospects in the deal, Owen Caissie, made his big league debut last season at age 22 and posted -0.1 WAR in 12 games.

As for the other three prospects involved in the trade, two of them have already been released from the Cubs’ organization, and the other (22-year-old Reginald Preciano) has yet to reach Double-A.

Given Chicago's crowded outfield, Caissie was traded to the Miami Marlins this offseason for right-handed starter Edward Cabrera. As for Preciano, he struggled mightily in 2025, but time is still on his side.

Former Cub Owen Caissie | Patrick Gorski-Imagn Images

So, with all this in mind, how did Chicago do on the deal? Their grade should be a C+ at best. -1.1 WAR to 6.9 WAR isn’t exactly close. That said, Caissie provided value in a different way, being used as a major trade chip. Also, given the large salary remaining on his deal ($63 million over three years), they did well to dump Darvish’s contract, especially considering he had one strong season with the Padres and given the free agent value of WAR).

All in all, though Darvish had a solid tenure with the Cubs, moving on from him wasn’t a bad choice. Given the current state of the franchise and the nature of signing a 31-year-old to a six-year, $120+ million deal, things could’ve ended worse.

Chicago moved on from Darvish at the right time, freed up some money, and still has some potential prospects in the aftermath that can contribute to winning in 2026 and beyond.

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