Yu Darvish's San Diego Legacy: Remembering A Huge Trade Win for Padres

Much is made of A.J. Preller's penchant for trading prospects. In many instances, the San Diego Padres' team president has given a lot -- perhaps too much -- to get a lot in return. The list of "hits" collected by the other teams is long and growing.

But one of those trades didn't have the desired effect for the team collecting the kids. It's the deal that brought Yu Darvish to the Padres from the Chicago Cubs. With Darvish nearing retirement or a separation from the Padres, it's worth looking back at the trade and noting how big a win it was for San Diego.

For reference, this was the full trade, which was announced on Dec. 29, 2020: 

PADRES RECEIVE:
RHP Yu Darvish
C Victor Caratini

CUBS RECEIVE:
RHP Zach Davies
OF Owen Caissie
OF Ismael Mena
INF Reginald Preciado
INF Yeison Santana

The move was a part of Preller's ambitious plan to revamp the rotation. On the same day Darvish became a Padre, the club acquired Cy Young Award-winning left-hander Blake Snell from the Tampa Bay Rays for a package led by Luis Patino. Four months earlier, Preller obtained Mike Clevinger from Cleveland for a prospect haul (more on that later).

The Cubs were never going to match either return. In the 2020-21 offseason, they were facing a payroll crunch with their young core players -- in particular, Javier Baez, Kris Bryant and Anthony Rizzo -- and Darvish had three years and $59 million remaining on his contract. He dominated in the COVID-shortened 2020 season after years of solid but unspectacular results, tying for the MLB lead with eight wins and posting a 2.01 ERA in 76 innings over 12 starts, but durability was a question mark ahead of his age-34 season.

Given that context, it's little wonder the Cubs executed a salary dump. Davies was a rental, as he signed with the Diamondbacks in January 2022. (For the record, Caratini was a rental for the Padres). Mena, Preciado and Santana were international lottery tickets, while Caissie was a high school hitter whom the Padres selected in the second round of the five-round 2020 MLB Draft.

Two of those tickets have been torn up. Santana was released in June 2023, and Mena was released last August. Preciado is still active, but he hasn't advanced past High Single-A yet, and last year, in his fifth pro season, he compiled a .218/.292/.382 slash line (.594 OPS). He'll be in his age-23 season in 2026.

Caissie, 23, became the Cubs' best hope for salvaging the trade. He reached the majors last year, with the British Columbia native making his debut Aug. 14 in Toronto. But on Jan. 6, he and minor-leaguers Edgardo De Leon and Cristian Hernandez were traded to the Miami Marlins for right-hander Edward Cabrera. 

With the Cubs getting barely any production from Caissie -- and none from the other prospects -- the contrast between the return for Darvish and the young players Preller sent the budget-conscious Tribe for an arbitration-eligible Clevinger --- Josh Naylor, Cal Quantrill, Gabriel Arias, Joey Cantillo and Owen Miller -- could not be starker. 

Darvish had an uneven tenure with the Friars. The peak was his 2022 season, when he posted a 3.10 ERA (3.31 FIP) and the club went 18-12 in his starts. The performance earned him a six-year, $108 million contract extension in February 2023. Over time, he became a leader of the pitching staff and a resource for younger teammates. But the past two seasons were cut short by injuries and a personal matter. Last year, his ERA ballooned to 5.38 (4.82 FIP). Now, at 39 and facing a lengthy rehab from elbow surgery, he's poised to leave San Diego three years early,

The Padres didn't get great value from the extension, but overall, they got their money's worth from Darvish, mostly because they paid just pennies on the dollar to acquire him.