Joba Chamberlain is one of the more honest former athletes. He’ll often weigh in on topics surrounding the New York Yankees, from in-game moves to potential free agent signings. That honesty doesn’t just stop at what the organization should do this winter. It also extends to the personal relationships he had in the game.

Chamberlain vs. Youkilis

When asked about which teammate he disliked from his playing days, Chamberlain gave a sincere answer. He said it was Kevin Youkilis. Even as teammates, Chamberlain said they had a frigid relationship from his years with the Boston Red Sox.

“I just didn’t like him when he was with the Red Sox or whatever, but he never came and got me, and then he was my teammate,” Chamberlain expressed on the Eddie Mata Show, on YouTube. “And I was like, Dude, this is baseball, like, between the lines, it is what it is, but outside, like, you’re my teammate … and then I called him right when he signed, and ignored me, ignored me, ignored me. And then he gets a spring training and wants to be all buddy-buddy, and then he breaks his back and doesn’t do anything for us. So that guy can go fly a kite.”

There aren’t many fans who will be jumping out of their seats to support Youkilis either. Chamberlain, the former World Series champion who had one of the more exciting rookie seasons a young pitcher can have, may not have liked his former teammate on an individual level, but he was also one of the many failed bargain bin moves the Yankees tried to make work after that 2009 season.

The Failed Red Sox Experiments

If there’s an antonym for the phrase “bursting on to the scene”, that would describe Youkilis’ 2013 season. That year, he played in 28 games. He hit .219 with a .648 OPS. His career ended in pinstripes.

Of course, the Yankees’ acquiring former Red Sox from that era didn’t stop there. A year after Youkilis’ failed deal, they signed Jacoby Ellsbury to a significant multi-year contract. If Youkilis went out with a whimper, Ellsbury became the gift that kept on giving, as he became progressively worse and worse as each year wore on.

The modern version of the former Red Sox player who failed in New York is Alex Verdugo, who had an excruciatingly long single season in pinstripes. Verdugo provided good outfield defense, but the Yankees won despite him, just as they did in 2017 with Ellsbury. Verdugo sported a .647 OPS in 2024. He did catch a few fly balls, and his barking was fun in April, but that’s as far as his contributions went.

If the Yankees want to keep the failed Red Sox experiments rolling, Lucas Giolito could be a name to look for. His peripheral stats, according to Baseball Savant, make him an obvious regression candidate.