A classic Brian Cashman mistake signs with perfect organization to revive his career

We're still waiting for Hot Stove season to really get cranking, but we finally got at least something to talk about on Monday afternoon. According to ESPN's Jeff Passan, the Milwaukee Brewers have signed right-handed pitcher Deivi Garcia to a Minor League deal, giving him a chance to compete for a spot at the back of the team's rotation or (more likely) in the bullpen.

Just looking at his recent numbers, those chances would seem to be pretty slim. Garcia spent this past season with the Chicago White Sox organization, where he put up a 6.18 ERA over 51 innings in Triple-A and an even uglier 7.07 mark in 14 innings at the Major League level. Chicago was desperate for any sort of pitching help, and even they refused to give Garcia extended run.

But not too long ago, Garcia appeared to be on a very different trajectory. Before he became just another in a long line of Yankees prospects squandered under Brian Cashman's watch, Garcia was the crown jewel of New York's farm system and one of the better pitching prospects in the game. He's a long way from that now, but if there's any of that old upside in there, the Brewers are the perfect team to unlock it — and maybe make the Yankees look awfully foolish in the process.

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Brian Cashman and the Yankees badly mismanaged Deivi Garcia's development

Signed out of the Dominican Republic as a teenager, Garcia tore through the Yankees system, getting all the way to Triple-A before his 21st birthday. He was a consensus top-100 prospect entering 2020, and New York was so high on him that they chose to throw him directly into the fire when injuries wrecked the team's rotation that same year. Garcia fired six shutout innings against the Toronto Blue Jays in his MLB debut, and while there were bumps in the road, he finished with a 4.98 ERA, a 4.15 FIP, three quality starts in six outings and 33 strikeouts in 34.1 innings — not too shabby for a guy who'd barely gotten his feet wet in the high Minors trying to adapt on the fly during a global pandemic.

Unfortunately, that was the high point of Garcia's Yankees career. New York surprised everyone by naming Garcia the starter for Game 2 of their ALDS against the Tampa Bay Rays, then pulling him after just one inning in an eventual loss. Then, that offseason, the team inexplicably decided to tweak his mechanics, changing his arm slot and completely ruining his command in the process. Garcia was dreadful in 2021, and despite reverting back to his old mechanics in 2022, his performance didn't improve. Less than three years after starting a playoff game, the Yankees cut ties with the righty, who was eventually claimed off waivers by Chicago.

"Young prospect flashes real potential that goes unrealized" has become something of a theme in New York in recent years. Whether it's Justus Sheffield or Clint Frazier or Miguel Andujar or Estevan Florial, Cashman has developed a nasty habit of choosing the worst of both worlds: never trusting his Minor Leaguers enough to give them real MLB experience, but also refusing to deal them while they still have real value on the trade market. If the Yankees were concerned about Garcia's mechanics, they could've traded him to any number of teams ahead of the 2021 season. Instead, they tanked his career, only moving on when no one else would take him off their hands.

Brewers are the perfect place for Deivi Garcia to get back on track

It bears repeating that Garcia's stuff was never the problem; he just could never put it in the strike zone consistently. But he's still just 25 years old, the arsenal remains Major League-caliber, and he's just gone from the worst organization in baseball to one that's established itself as a pitching development machine in recent years.

From the rotation to the bullpen, there's no end to the pitchers that Milwaukee has been able to rehabilitate. Tobias Myers went from afterthought to ace in 2024; Colin Rea was in Japan two years ago, and now looks like a perfectly cromulent fourth or fifth starter. Trevor Megill, Jared Koenig and Elvis Peguero were all anonymous before blossoming into stars in Milwaukee's bullpen of late.

Maybe Garcia won't join that list; his command problems are very real, and that's not to be taken lately. But if he does pan out in some way in 2025, it'll serve as a reminder of what a difference a good support system can make, and of how badly the Yankees dropped the ball here.