Once the New York Yankees reached an agreement with Aaron Judge on a blockbuster nine-year, $360 million deal, they turned their attention to addressing notable team needs. Judge does not have a final say in any free agency matters, but according to the New York Post's Jon Heyman, he “made two suggestions” to the team.

Heyman noted that Judge aspired to see the Yankees bring in a “strong” starting pitcher and re-sign Andrew Benintendi.

Yankees general manager Brian Cashman did manage to haul in a highly coveted starter, coming to terms with Carlos Rodon on a six-year, $162 million contract deal in late December. However, he failed to keep Benintendi with the reigning American League East champions, as the left fielder ended up taking his talents to the Chicago White Sox on a five-year, $75 million deal.

Heyman added that the Yankees did at the least make a push to come to terms with Benintendi on a multiyear contract. The Yankees “made an offer” to the one-time All-Star and were “willing” to sign him to a four-year deal. In the end, he sided with Chicago’s five-year offer.

Benintendi recently told Heyman that at the end of the day, Chicago’s free agent offer was one that he simply could not turn down.

“It was an offer I couldn’t refuse,” Benintendi said. “This is where I wanted to be and where I should be. It’s not something specifically where I wanted to stay in the Midwest. But as far as the teams that were interested, I think this was the best fit.”

Benintendi’s half-season run with the Yankees was ultimately cut short after he suffered a right wrist injury in early September, and he went on to miss the entirety of the AL East side's postseason run.

“It was definitely frustrating I wasn’t able to play in the playoffs,” Benintendi said. “I think if we won the championship series maybe I would have been ready for the World Series, maybe. It would have been a push. But I would have probably tried.”

Benintendi posted a .304 batting average in a combined 126 regular season contests played with the Kansas City Royals and the Yankees in the 2022 campaign.