Yankees' Brian Cashman Wins Deadline War Against Rival GM

The MLB trade deadline has come and gone, and once again, New York Yankees general manager Brian Cashman proved why he's among the best in the business. The same cannot be said for Boston Red Sox chief baseball officer Craig Breslow.

Cashman made five trades. Among his haul were relievers David Bednar, Jake Bird and Camilo Doval. He also picked up shortstop José Caballero and outfielder Wilberson De Pena.

Don't forget that before the deadline, Cashman also added outfielder Austin Slater and infielders Ryan McMahon and Amed Rosario.

Breslow made two trades, landing starter Dustin May and reliever Steven Matz. His only other pre-deadline deal of note was shipping All-Star slugger Rafael Devers to the San Francisco Giants in June.

In fact, Breslow took a prospect from the Devers trade, outfielder James Tibbs III, and sent him to the Dodgers for May. Tibbs was the No. 5 prospect overall for the Red Sox. And keep in mind, May is a short-term rental who will be a free agent after the World Series.

Cashman, in completing all those deals Thursday, held on to his top five prospects, including No. 1 George Lombard Jr. and red-hot slugger Spencer Jones. And when Cashman used his No. 8 prospect, catcher Rafael Flores, he received an All-Star closer who is under team control for the 2026 season.

ESPN's David Schoenfield called the Yankees one of the trade deadline winners, noting they didn't get a starting pitcher but "dramatically improved their depth and versatility."

On the flip side, Schoenfield called the Red Sox one of the trade deadline losers.

"The Red Sox could have traded for a first baseman or gotten creative and dealt from their logjam of outfielders," Schoenfield wrotte Friday. "It's understandable they didn't want to do that now, given they've gone 17-7 in July. Why mess with that momentum? Still, a better starting pitcher than May or an impact reliever would have helped."

And that's just the tip of the iceberg. The Athletic's Ken Rosenthal slammed Breslow and the Red Sox following the deadline.

“Epic fail. Comes off am an epic fail at last year’s deadline with Craig Breslow, and this was an epic fail, as well," Rosenthal said. "Joe Ryan was another starting pitcher who wasn’t traded, but my understanding is any talks that they had with the Twins were feeble at best. They didn’t come at them hard.

“The Red Sox are one of many teams that uses modeling and tries to figure out what the best values are," Rosenthal continued. "And it’s all about efficiency and getting the best deal and this and that and the other thing.  At some point, you’ve got to fire. …

“And they did not even address first base, which I know they’ve gotten decent work out of Romy González and Abraham Toro, but my goodness, that was a position where they had to act," Rosenthal noted. "They tried for Eugenio Suárez, and they tried with the idea of playing him at first base. Didn’t get him. Didn’t get a starter other than Dustin May, who has not been a very successful starter for the Dodgers. And their bullpen with Steven Matz, he’s a swing guy, he can be effective. But my goodness, they needed more.

“This is a team that is on the rise. And again, they may say, ‘We’re gonna be better next year. Our young guys will be that much better.’ Yeah, that’s what the Orioles were saying a year ago. There is no guarantee in this sport, or any other.

“So the Red Sox, I don’t get it. I don’t understand it. And there’s gonna be some people in Boston, a lot of people in Boston, questioning what the heck they did," Rosenthal concluded.

The Red Sox (59-51) take the field Friday in third place in the American League East, five games behind the first-place Toronto Blue Jays. Boston is 1 1/2 games behind the Yankees in the American League Wild Card standings.

According to FanGraphs, New York has a 93.7% chance of making the playoffs. The Red Sox's odds are much lower: 61.2%.

If Boston should miss the postseason, Breslow and the Red Sox could regret their lack of activity ahead of the trade deadline.

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