In the end, it came down to Ortiz and a one-time protege -- Marlins superstar Hanley Ramirez.
After clubbing eight homers in the first round and 13 in the second, the lefty slugger left enough in the tank to drill 11 more long balls in the finals. Ramirez had the chance for the last laugh, but he came up well short, hitting just five.
This wound up being Ortiz's night, as he became the first Red Sox player to win a Derby. Who could have envisioned this in April, when Ortiz mustered just one homer and four RBIs while hitting .143 and being reduced to platoon status?
"Well, when I go through the downs, it makes me even stronger," said Ortiz. "It just teaches me that never take anything for granted. When you're doing well, you want to just stay at that level, so when the down shows up, it doesn't do that much damage. My problem was that it was just the beginning of the season and you haven't done anything yet."
It was also Boston, where things get, well, magnified.
"So it looked bigger than usual," said Ortiz, who had an even more horrific start to the 2009 season. "But in my case, it wasn't that 'He's going to be fine.' It was that 'He's done,' you know, which is even worse. But like I say, man, I'm a guy that you have to knock me out really hard to never get back up. That's how I am."
But there was never a knockout punch -- not from Red Sox management or American League pitchers. He is back among the best in the game, and relishing the spotlight.
"I've been doing it so many times the last few years, and coming back here and being chosen [as an All-Star] by the players around the league, that really gave me a lot of excitement," said Ortiz. "I think that's one thing that I want to say -- I thank the players for giving me the opportunity to be here and knowing that I'm one of the guys that like to do the right thing.
"Like I always say, this is a job that we have, but the name of it is a game, and what we know about that name is to have fun, and that's what I try to do. Even during the season, have fun with my teammates and make sure everything goes the right way. That makes things easier."
Competing with Ortiz for the Derby title was something that Ramirez embraced.
"He loves to have fun," Ramirez said. "He's unbelievable. He's one of the best people I've ever met in my life. I know he's going to come back and do what he gets paid to do -- hit bombs. The most important thing tonight is that we were all rooting for each other. Nobody was rooting for himself. We had fun."
Even as Ramirez was trying to win the contest, Ortiz stepped in and told him to slow down and try to conserve some of his energy.
"I told him, 'Hey, take it easy, don't get too tired, take your time, because that's what the Home Run Derby is all about.' I'm not really worried about winning or losing," Ortiz said. "I'm worried about the fans having a good show, and I think he did a hell of a job."
And yes, it was a Yankee who helped Ortiz become victorious for the first time in four tries in the Home Run Derby. At least it was a Yankee with a Red Sox connection. It was none other than New York bench coach -- and former Boston catcher Tony Pena -- who served up Ortiz's Derby missiles.
"It was unbelievable," Ortiz said. "Tony, he's got the great mechanics as a catcher. And I saw him before, and whenever we go to play the Yankees, I see him throwing batting practice. And as soon as I found out he was going to be here, I was like, 'Tony, can you pitch to me?' He was like, 'Fine. No problem. I'm going to throw to [Nick] Swisher, but I'm going to throw for you, [too].' We are here for the fans. It's not a Yankees/Boston situation. We are here for the fans, so let's do it."
Another thing that aided Ortiz in his Derby victory was the placement. He batted sixth out of eight contestants in the first round, but then led off in both the second round and the finals.
"It was good that they put me towards the end, because I get tired pretty easy when I hit and shut it down for a while," Ortiz said. "So when I don't have to wait that long period of time, I guess it helped me out."
There were predictions earlier in the day that Ortiz would come out on top -- some from his current teammates and one from one of his favorite former teammates.
"A lefty was going to win this thing," said Angels center fielder Torii Hunter, who used to play with Ortiz on the Twins. "I know my ballpark. I know it's a lefty friendly park at 7 o'clock. When I found he was going to be in it, I told he was going to win it. He was my pick to click."
"It's impressive. I knew he was going to win it," said Red Sox third baseman Adrian Beltre. "I felt it. He felt good about it. It was fun and it was good for him."
Aside from Ortiz's inner resolve, his friends from around the game also helped to keep his confidence up during that rough opening month.
"I told him in April he was going to be in the All-Star Game," said Hunter. "That's my buddy -- you have to lift him up."
Now, Ortiz is very much back up, with a trophy -- which he is donating to the family of the late Jose Lima -- to prove it.
"Not everything is roses and flowers," Ortiz said. "You've got to deal with the downs so you can get up. You know, I've been a guy that I've been a force as long as I've been playing here with the Red Sox, and I've had a lot of ups, a lot more than downs, and as soon as I have a down, it seems like everybody is pointing at me like a Nintendo game or something that is supposed to be that easy. We have to work hard to get prepared to play the game and we have to do a lot of things to maintain ourselves -- myself -- at that level."
There is no longer any dispute -- either in Boston or around the baseball world -- that Ortiz has regained his level.
Ian Browne is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.