How the Darvish trade came together between Cubs and Padres

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On the phone with Victor Caratini Tuesday night, Cubs president of baseball operations Jed Hoyer told the outgoing catcher that he still remembered making the trade for him in 2014.

That, of course, wasn’t the focus of the call. The Cubs and Padres finalized a deal to send Caratini and ace Yu Darvish to San Diego for right-hander Zach Davies and four prospects. But it was a full-circle moment for Hoyer.

“That was the last deal we made before this six-year run,” Hoyer said in a Zoom press conference Wednesday. “That was the last trade in the other direction that we made. And we got a really good young player for a left-handed reliever and utility guy. When people question the value of getting young players and acquiring depth and doing those things, that's a good example of a trade that really benefited us, and he developed wonderfully.”

Hoyer wasn’t saying the parallels were exact. The 2014 trade included three players; this week’s trade included seven. James Russell was a bullpen workhorse; Darvish was the Cubs’ best player last season. And so on, and so forth.

The two trades involving Caratini did, however, bookend an era in Cubs baseball.

“Do we need to make some moves with the future in mind, after six years of every single move being directed on the present?” Hoyer said Wednesday. “Yes. I think that's the prudent thing to do.”

That’s how Hoyer found himself evaluating a young prospect-heavy return as “by far the most appealing deal” discussed with the Padres.

All four of the prospects the Cubs acquired from San Diego this week – infielders Reginald Preciado and Yeison Santana, and outfielders Owen Caissie and Ismael Mena – the Cubs scouted at instructional league this fall.

They had also scouted Caissie, who the Padres selected No. 45 overall in the 2020 MLB Draft, leading into this past summer. The other three, the Padres acquired during the international signing periods of the past few years. But the cancelled 2020 minor league season created an information gap.

“It's a challenge,” Hoyer said. “Not only with these players we acquired, but for all players. It probably leads to more information asymmetry than usual, which isn't necessarily a bad thing in these in these processes.”

With a staff shrunken by this year’s layoffs, the Cubs had to pick and choose the teams that they would focus their scouting efforts on. They eliminated teams that weren’t likely to compete this season or trade prospects. The Padres were one of the clubs remaining.

Both Hoyer and Padres general manager A.J. Preller said they discussed different ways to structure a potential trade. At the same time, San Diego was negotiating with Tampa Bay for left-handed pitcher Blake Snell, which added a “fluidity” to the weeks-long talks, Hoyer said.

The Padres were “insistent upon” including Caratini in the trade, according to Hoyer. As Darvish’s personal catcher for the past year and a half, Caratini could help smooth the transition for Darvish and strengthen the team at his own position.

For the Cubs, an avenue to bolster their pipeline looked enticing.

“They’re getting four really good young players to kind of kickstart that farm system,” Preller told reporters Tuesday night.

MLB Pipeline ranked all four of them just outside of the Padre’s top 10 prospects. All but Santana, 20, are teenagers, giving them high ceilings. But it will also be years before they are ready to contribute to a big-league team, even if their development goes to plan.

Asked where the Cubs’ Gleyber Torres or Eloy Jimenez was in this trade, Hoyer paused. Both former Cubs prospects were known commodities when the Cubs traded them in 2016 and 2017 as parts of the packages for closer Aroldis Chapman and southpaw José Quintana, respectively.  

“Every single year there's a higher value of prospects,” Hoyer said, “As the industry lost $3 billion and as things contract, I do feel like, by definition, people are going to hold on tighter to those close-to-the-big leagues prospects.”

Even after leveraging their strong farm system to acquire catcher Austin Nola and pitchers Mike Clevinger, Snell and Darvish in the past four months, the Padres have managed to hold onto three of their preseason top-5 prospects, as ranked by MLB.com.

“There's no question when you look at this return,” Hoyer said, “you're going say it's young and there's risk involved. And I think that's a fair thing to say. But you also could say, these are four really talented young players. Given where they were drafted, given the amount of money that they signed for, where they rank in their (home) countries, these are four really talented kids that I can't wait to turn over to high performance, I can't wait to turn over to our player development guys.”

Maybe years down the line, Hoyer will call one of those four players to tell him he’s been traded, after establishing himself with the Cubs. And just like with Caratini, Hoyer will reminisce about the trade that brought him to Chicago. A trade that marked a new chapter of Cubs baseball.

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