Don Orsillo and Xander Bogaerts just dealt Red Sox fans a painful reminder

Two former Red Sox icons gave Red Sox fans a reminder of what they're missing.
Boston Red Sox v San Diego Padres
Boston Red Sox v San Diego Padres | Orlando Ramirez/GettyImages

The Boston Red Sox moved on from Xander Bogaerts after the 2022 season, and announcer Don Orsillo after the 2015 campaign. Ironically enough, the pair reunited when Bogaerts signed with the San Diego Padres in free agency. At the time, both symbolized failures by the Red Sox organization to hold onto their homegrown stars. Orsillo was the voice of a generation of Red Sox fans, while Bogaerts was the kind of infielder Chaim Bloom could have built around, but didn't.

Boston has since been vindicated for losing Bogaerts, as he struggled to live up to his 11-year, $280 million contract in San Diego. However, the script has flipped in August for Xander, who entered the Padres series against the Red Sox red-hot. While losing Bogaerts hasn't exactly come back to haunt the Red Sox – and Boston replaced Orsillo long ago – Boston fans can't help but wish both were around for the 2025 season and a hopeful postseason push.

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Xander Bogaerts hit a home run against his old team, the Boston Red Sox

Bogaerts hit a home run on Saturday against Red Sox starting pitcher Lucas Giolito, prompting some postgame questions regarding the extra motivation of playing against his former team. Xander avoided taking shots at Boston – he's happy to be playing in San Diego – but he did make sure to shout out the Red Sox-turned-Padres broadcaster Orsillo in his postgame interview.

"I have a lot of memories..and with Don, my first couple years in the big leagues Don was there. It's a new team, but it's still the Red Sox..a place always close to your heart..," Bogaerts admitted.

Orsillo responded to Bogaerts comment, as the two are close off the field.

"I love you Bogey! So glad we are together for both of our 2nd chapters and can’t wait to win another ring together," Orsillo said.

Red Sox fans are still heartbroken about losing Bogaerts and Orsillo

Since mid-June, Bogaerts ranks first among MLB shortstops in fWAR, wRC+ and wOBA. He's been scorching hot, once against prompting the discussion of whether the Red Sox should have given up on him in the first place. Hindsight is 20-20, though, and the Red Sox are doing just fine without the former face of their franchise. The same can be said about Rafael Devers, who has struggled to acclimate to San Francisco while the Red Sox thrive.

"I swear to god the sun shined brighter when you were both in Boston," one Red Sox fan wrote on X.

"Don Orsillo, we still love you! Signed, Red Sox Nation," another Sox fan said.

Two things can be true. Yes, the Red Sox made the right call not giving Bogaerts $280 million. However, that doesn't erase the pain of watching a homegrown fan favorite thrive elsewhere.