Speaking to reporters on Monday, he explained the team's position while acknowledging the pain of losing a beloved player in the prime of their career.
"I grew up a fan of the St. Louis Cardinals," Henry said. "My favorite player was Stan Musial. My heart would have broken if 'Stan the Man' had ever been traded - for any reason. Your parents or your grandparents surely felt the same way about Ted Williams and Yaz (Carl Yastrzemski).
"So, on one level, when I say I understand how many of you feel about this trade with the Dodgers, I know many of you - particularly our youngest fans - are disbelieving or angry or sad about it. I know it's difficult and disappointing."
Henry went on to compare the Betts trade - which also included left-hander David Price - to the time Boston dealt shortstop Nomar Garciaparra to the Chicago Cubs in 2004.
He added that Betts' impending departure via free agency played a significant role in the difficult decision. Ownership ultimately felt that trading the 2018 AL MVP for Alex Verdugo, Jeter Downs, and Connor Wong was better than receiving a compensation pick next offseason if Betts' signed elsewhere after rejecting a qualifying offer.
Henry said he personally told Betts that he wanted him to spend his entire career with the Red Sox and that Boston made overtures to the four-time All-Star regarding a new contract over three different offseasons, according to MLB.com's Ian Browne.
"I understand there is probably little I can say today that will change how you feel about this," Henry said, "but it is my responsibility to try."