That's three more times than the previous 86 years under various ownerships before the Red Sox won it again in 2004.
"For us to win a fourth championship would be the cornerstone of the careers of everyone involved here, who've been involved in these three," Henry told a group of reporters at a media conference. "Already there's a sense here that 2013 was 2013. There are a lot of pictures up, that were put up last week, about what happened in 2013. I think most of us are trying to look forward. We have already turned the page. But winning a fourth one, in our eyes, is going to be just as difficult as the first one was."
Still, with all that success the Red Sox have not been able to repeat.
"We've done a lot of studying," Henry said. "It's certainly not all data or metrics. When you look at the difference between the 2012 and 2013 teams, I recently talked at length about that in a speech that I gave to the Boston Chamber of Commerce about how hard it is to predict anything going into any season. No one picked either the Red Sox or Cardinals to get to the World Series last year.
"You'd think someone by accident would pick one of the participants in the World Series. I would say more than anything else, it's what happens out there between the lines. You can do everything right and sometimes you can do things quite a bit wrong and get a good result."
During the 16-minute interview session, Henry touched on a number of topics, including the lifespan of Fenway Park, the economics of the team and a replacement for Commissioner Bud Selig, who is set to retire early next year, among other things.
About Fenway, he said that with the improvements that current ownership has made, the ballpark can stand for another 30 years. Thus, replacing it will be the decision of another ownership group.
"Structurally there is an expiration date," Henry said. "Someone in the decades ahead will have to address the possibility of a new ballpark. As far as more changes, we need to deal with the press box. It's just not great. Is there anybody here who likes the press box? We've taken care of the fans. At some point, we need to deal with that. So we'll be doing smaller things at the top, perhaps, but you won't see major changes. Those have been explored, thought about and accomplished."
About the long-term contracts that have been paid out this offseason by other clubs, Henry said, referring to the contracts, now shed, given to Adrian Gonzalez, Carl Crawford and Josh Beckett: "I think we did that for a period of time, a short period, but we learned from it and a few other clubs have learned from it. All you have to do is take a look at the results over, say, the last 10 years, of what kind of an approach that has meant. It's a very, very risky thing to do. I don't see us necessarily changing."
Asked if the $189 million competitive balance tax threshold would be the ceiling for Boston's player payroll moving forward, Henry said:
"It has been. There's some reason to believe that it may not be as important as we thought a couple of years ago. We feel that at that level you're either at the top or near the top of the payroll structure. There were certain incentives that were built in that at the time I doubted would really carry the day. And that appears to be the case. It probably won't."
About a replacement for Selig, Henry was asked if he had any thoughts.
"I do," he said.
Can you share them?
"Oh, no, no no. But this much I can say: He will be extraordinarily difficult to replace, extraordinarily difficult. That process is underway, but it'll be extraordinarily difficult."
About Ryan Dempster's unexpected announcement that he wouldn't pitch in 2014, Henry said: "I think I was a rookie when he was a rookie. Maybe his first year was my second year with the Marlins. So I know what a big loss Ryan is in the clubhouse. But that's part of the challenge. Every year you're going to be faced with challenges. Losing Ryan is a tough loss. It affects our depth as well."
Asked about the success of the franchise under his ownership, Henry said: "I feel extremely fortunate to be part of this. We've had 12 seasons here now that have been just incredible. I was thinking yesterday, I'm just thankful to be part of it in whatever role I've played in it. I'm so thankful that we were able to come here in the first place. We have a certain philosophy that is a valid philosophy. It doesn't matter what resources we can bring to the table, we still have to have 25 guys and another 25 behind them, plus coaching, a manager and a general manager. You have to be fortunate to have the right team in place."