Xander Bogaerts' Joke on Roman Anthony Will Hit Red Sox Fans in the Feels

Some contracts happen, some don't

Mar 26, 2026; San Diego, California, USA; San Diego Padres shortstop Xander Bogaerts (2) walks off the field during the second inning against the Detroit Tigers at Petco Park. Mandatory Credit: David Frerker-Imagn Images | David Frerker-Imagn Images

Roman Anthony is the new early-20s phenom of the Boston Red Sox, but before him, there was once Xander Bogaerts.

Bogaerts, now the 33-year-old five-time All-Star shortstop for the San Diego Padres, played the first 10 seasons of his excellent career in Boston. As he prepared to face the Red Sox this weekend, one might have thought he would know exactly what it would be like to be in Anthony's shoes.

However, there's one major difference between their two experiences, which Bogaerts quite humorously pointed out.

Xander Bogaerts on Anthony's extension, talent

Sep 2, 2025; Boston, Massachusetts, USA; Boston Red Sox right fielder Roman Anthony (19) hits a one run hits an RBI single against the Cleveland Guardians during the second inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

“He came up and got an extension right away. I can’t relate to that,” Bogaerts said, via Rob Bradford on X.

Red Sox fans won't soon forget the feeling of the night in the dead of winter before the 2023 season in which they learned that Bogaerts had agreed to an 11-year, $270 million contract with the Padres. Even if it would have been totally irresponsible to match those years and dollars, it felt as if he was supposed to stay in Boston for life.

Of course, Bogaerts had signed one extension with the Red Sox, a deal that was supposed to be six years, $120 million, but only lasted three after the shortstop opted out.

With veterans from the last Red Sox championship all gone, namely Bogaerts, Rafael Devers, and Mookie Betts, a burden has fallen on Anthony's shoulders that even Bogaerts can see plainly.

“That (extension) probably comes with a little bit more on his shoulders. He might be the face of the team right now,” Bogaerts said, via Bradford. “When you think of all that happened last year, he’s probably the guy.

"He’s a really good player. I’ve never met him, never played with him in the minors or anything like that. I don’t know the kid. All I know is he’s very good at baseball and is a nice kid, also, from what I’ve heard.”

As Boston attempts to dig itself out of the 1-5 hole in which it finds itself, it faces a Padres team this weekend with two reminders of past transactions gone amiss: Bogaerts' free agency departure, and Walker Buehler, who signed a minor-league deal with the Padres after the Red Sox released him from his $21 million deal last August.

Some wins this weekend would go a long way toward restoring the good vibes, to put it mildly.