Because Henry defers to president/CEO Larry Lucchino and general manager Theo Epstein and his staff on baseball decisions, the owner wound up approving the second-most lucrative free-agent signing in club history.
"It was definitely a baseball signing," Henry told hosts Michael Felger and Tony Massarotti on CBS Radio's Boston affiliate. "In fact, anyone involved in the process, anyone involved in upper management of the Red Sox would tell you that I personally opposed that. They all know that."
"Why? Because we had plenty of left-handed hitting. I don't have to go into why," Henry said. "I'll just tell you that at the time, I opposed the deal. But I don't meddle to the point of making decisions for our baseball people. This was driven, and Theo will tell you, it was driven by our baseball people. It wasn't a PR move. Neither was the [Adrian] Gonzalez [trade and eventual] signing."
Crawford had a rough first season in Boston, hitting .255 with a .288 on-base percentage while also having his share of struggles in left field.
As for Epstein, he continues to go to his office at Fenway Park each day amid the reports that he's agreed with the Cubs on a five-year contract.
The Red Sox and Cubs both know that Epstein can only move to Chicago once the sides agree to a compensation package that satisfies both sides. Epstein is under contract to the Red Sox for one more year.
Though Henry made it clear his preference was for Epstein to return, the tone of his voice indicated the inevitability that Chicago is where his GM of the last nine seasons will end up.
"I'd love to have Theo back," Henry said. "I would have loved for Theo to have been our general manager for the next 20 years. That was my hope. That would have been my hope. But you don't always get what you want. I did everything I could personally and so did [chairman] Tom [Werner] and Larry to make that happen. The fact is, I think people don't understand this, the fact is, being general manager in Boston, being manager in Boston, is a terrifically tough job."
Henry also said that he suggested during the season that the organization pick up manager Terry Francona's options for the 2012 and '13 seasons.
"At one point during the season, I actually sent out an e-mail to the rest of the guys in upper management and said, 'Unless we think we're going to find a better manager, we should pick up the options.' Then I was reminded why we had the options, why we negotiated the options. There are a couple of people in our organization whose pet peeve is picking up options before their time. It doesn't matter who it is. You negotiate. He negotiated a certain amount of dollars and years; we got options. Tito was great about it. He never said a word about it. I was the only one who said a word about it."
Henry said he was convinced Francona shouldn't return only after the manager himself told the ownership group and Epstein two days after the season that a new voice was needed to lead the team.
The owner was remorseful about the Francona-Epstein era coming to an end.
"We've had great management," Henry said. "Tito and Theo have brought World Series -- two World Series here. Arguably the best general manager in my mind and the best manager. It's just really a sad day to see them both leaving."
But Henry assured fans that he has no plans of going anywhere soon, and neither does Lucchino.
While Lucchino's contract runs out at the end of this calendar year, Henry said that his president/CEO definitely plans on returning for several more years.
How long does Henry plan to stay on as owner of the Red Sox?
"As long as I can," he said. "I love this. It broke my heart to see this club fall apart at the end. If you look at any of the film after we lost that game in Baltimore, that's how all of us felt. We were devastated to lose that last game, the way that it happened."
The 7-20 September is something that will probably stick with Henry until the day pitchers and catchers report to Spring Training in February.
"It's devastating," Henry said. "You work, you invest ... I watch 162 games, or 159, 160 games. Every pitch, every inning. You put everything you can into trying to win a World Series, and then to have it fall apart at the end is frustrating. It's painful.
"I have to be as angry as upset as any fans are. If the fans hang in there, I'm going to hang in there. Larry is going to be back next year. We're going to be back as an organization. We're going to have a top class manager and general manager and we're going to have a great team next year.
"People forget now that this was a great team before September. They're concentrating solely on September. I love this team, and I'm going to do everything I can to get it back to where it needs to be."