Sure there were similar moments in 2004, and to a less dramatic degree, '07. But after going through some lumps as an organization the previous couple of years, this taste was sweeter to Henry than the champagne that sprayed around the clubhouse.
"It was a long time ago," Henry said of the previous trips to the World Series. "But I just don't remember anything more exciting than that ball [by Victorino] going over the wall. I'm sure we've had some moments as exciting, but that's up there."
Before Victorino's homer gave the Red Sox the game-breaking hit they needed to finally silence the Tigers in a highly stressful American League Championship Series, Henry sought out some members of baseball operations.
"I was in baseball ops in the bottom of the seventh inning," Henry said. "I figured they were suffering more than I was because this was a tough, tough series. Before the first pitch, they said he was looking curveball. He was waiting for the curveball. He threw a curveball for a strike and we all went, 'Ohhhhhh.' Third pitch was a curveball and that was it. So, it's a tremendous organization."
General manager Ben Cherington -- the man Henry instantly entrusted to run his baseball operations department when Theo Epstein left for the Cubs two years ago -- was holed up in his office at the moment Victorino made contact. He was doing anything he could do to reduce his stress, be it reading emails or other administrative duties.
"I was trying to make sure my anxiety wouldn't affect others," Cherington said. "We've just been moving around. When you're watching every pitch in games like this, what happens is you know how much it mean to our players an the people in our clubhouse and we know how much passion they have for winning these games and we want it for them.
"Those of us in the front office, we're kind of just along for the ride at this point. When the games start, we're rooting so hard, we're fans, and every pitch is like an event. So some parts of the games are hard to watch. We enjoy grand slams and the last three outs when Koji [Uehara] is on the mound. That's about it."
In the next couple of days, leading up to the first pitch of the 2013 World Series, it will be hard for ownership and front office not to appreciate how rewarding this season's product has been.
It started with the entire organization trying to erase the bitter taste of the worst baseball summer Boston had seen in over 40 years.
Early on, it became clear these Red Sox would be different. And as the weeks turned into months, it was evident that something quite special was in full motion.
"Those of us in the front office, we know that not everything we do is going to work out," said Cherington. "Obviously there are mistakes -- my mistakes. Mistakes happen. When things are going well, you just sit back and try to enjoy it. We have a remarkable group of people in this clubhouse, [manager] John [Farrell] and his staff, and the medical staff, the players. They just set out to accomplish something and do it together -- do it the right way. We're just enjoying it. We're along for the ride and we're enjoying it."
It is reminiscent of the joy that took place early in the administration led by Henry, club president/CEO Larry Lucchino and Tom Werner, which took over the club in 2002.
"It's a different flavor of ice cream, but it tastes just as good," said Lucchino. "We know that '04 will always be special because of the 86 years that preceded it. But John Henry and I were joking just a few days ago about how good it feels this year as a result of the length that we've come, and the skepticism we faced."
The first step in the climb back to baseball's elite started late in the summer of 2012, when the blockbuster trade was made with the Dodgers that sent Adrian Gonzalez, Carl Crawford, Josh Beckett and Nick Punto (not to mention over $250 million in salary) to the West Coast.
"The decision to reboot," said Lucchino. "That gave us the capacity to do so. But it still required us to find the right players and deploy the money successfully. Ben Cherington did a fantastic job with that, in the seven major acquisitions we made this offseason. We found a manager who was just perfect for this team and this time in John Farrell, and this time we were able to get him loose from our friends in Toronto. We thought it would be a good step in the right direction."
But who could have known that the right direction would lead all the way to the World Series?
"I certainly hoped for it and prayed for it, but I never planned specifically for it," Lucchino said. "We just wanted to take a big step in the right direction. We didn't think we could step this far, this fast."
"We weren't really thinking about it, but once we got into the season, and saw the team that was coming together and just the personality in this room, I don't know, you just stop getting surprised," said Cherington. "Because every time they were tested, they stepped up and met that test."