Yankees follow up Aaron Judge deal by taking a massive L to Red Sox

The New York Yankees may have gotten a win by re-signing Aaron Judge, but they watched a free agent target agree to terms with the rival Boston Red Sox.

The New York Yankees did not sound like a team that was confident in their ability to re-sign Aaron Judge, their star outfielder and 2022 AL MVP. There was the false alarm that claimed Aaron Judge (or Arson Judge) was likely heading to the San Francisco Giants on Tuesday night. But on early Wednesday morning, the Yankees were able to agree to terms with Judge on a nine-year, $360 million deal, ensuring he wouldn’t sign with the Giants or the San Diego Padres.

Even though the feeling in Yankee land was one of exuberance and relief, they received some bad news, and it’s related to the rival Boston Red Sox.

ESPN MLB insider Jeff Passan reported that the Red Sox have agreed to terms with Japanese outfielder Masataka Yoshida to a five-year, $90 million contract.

This is bad news for the Yankees since they were linked to him to fill their left field void.

Yankees watch as Mastaka Yoshida joins Red Sox

With this, the Yankees need to act fast to fill that void.

The obvious move would be for the Yankees to re-sign Andrew Benintendi, their trade deadline acquisition this past season. He showed promise in his 33 games played before his season ended due to a broken hook of his hamate bone.

Bringing Benintendi back won’t be easy, as he has reported interest from the Houston Astros and the Mets. But they do have some options in free agency.

New York could make a run at Brandon Nimmo, but only if they’re willing to go above and beyond to sign him, since he’s the top outfield free agent remaining. They could take a flier on Michael Conforto, who hasn’t played since 2021.

In terms of the trade market, the Yankees could try and get the Pittsburgh Pirates to acquire Bryan Reynolds. However, he will likely come at a cost of multiple top prospects, given his play and the fact that he’s under team control until after the 2025 season.

Yes, re-signing Judge was a massive win, but the job’s not done. They still need to make additions across the roster to ensure that they have a shot at defeating the Astros come postseason time.