But when Alex Rodriguez passed him on Friday night in the Yankees' 9-1 win over the Mets, Jackson somehow felt a little different. Because this time, he was being overtaken by a member of the Yankees -- the club he played for during the prime of his Hall of Fame career.
So despite whatever disappointment and frustration Jackson has felt in the past, he was able to put all of that aside on Friday. Rodriguez hit his 564th homer on Friday with Jackson watching in the Yankees' clubhouse. When the game was over, Jackson found a way to feel content -- at least for one night -- and to celebrate Rodriguez's accomplishment.
"The negativity that surrounds steroids is certainly not something I carry over to him," Jackson said. "I do appreciate the fact he admitted his mistakes, so from here, we move forward. Judgment on him will be passed over the next 7 1/2 years with the Yankees.
"Here's a guy who is probably going to end up with 700 or 800 home runs. I want to enjoy the night tonight and watch my friend hit No. 564 and maybe drop my name in the paper."
Jackson promised Rodriguez he would try to be in attendance when Rodriguez passed him, so he made the trek to Citi Field on Friday for the first game of the second installment of this season's Subway Series. Jackson was in the clubhouse watching with Yankees captain Derek Jeter, who missed the game with an illness, when Rodriguez hit the homer.
Rodriguez tied Jackson on Thursday in Atlanta, hitting a home run off Braves starter Derek Lowe. At the time, Rodriguez was mired in a deep slump and hadn't hit a home run since June 13.
Nevertheless, Rodriguez made sure not to waste any time before hitting his next one.
"When he hit the home run, I said, 'Oh man, nice going -- one day; I didn't have to wait very long,'" Jackson said. "I waited, like, a week for 563."
The milestone home run came in the eighth inning with the Yankees already up, 5-1. With Mark Teixeira on first base, Rodriguez launched a pitch off reliever Elmer Dessens into the Mets' bullpen in right-center field, driving the ball close to the 415-foot sign. Rodriguez went 1-for-2 with three walks and two RBIs in the win.
There was little immediate fanfare, but Rodriguez said he has since been given the ball. Afterward, when the two met, Jackson embraced Rodriguez in a big hug to express his congratulations.
"Reggie is a close friend and a mentor and someone who I've known since I was 17 years old," Rodriguez said. "This one is special."
Beyond that, Rodriguez was understated in the visitors' clubhouse after the game. He tried to keep the conversation focused on the Yankees rather than himself, as has been his custom so far this season. Rodriguez said he was pleased that Jackson was able to see the home run and spoke about their longstanding friendship.
"It's pretty special to have Reggie here," Rodriguez said. "I remember the first time I met Reggie was at an Upper Deck Classic in California when I was 17. Reggie is an American icon. He's done a lot of great things, and all the history he brings to the Yankees is special."
Next up for Rodriguez is Rafael Palmeiro's total of 569, which the third baseman is likely to break this season. Palmeiro tested positive for performance-enhancing drugs toward the end of his career. After eclipsing Palmeiro, Rodriguez will set his sights on Harmon Killebrew's total of 573 homers.
When that happens, talk of steroids will undoubtedly return. That will inevitably take place with each milestone Rodriguez reaches. Jackson acknowledged it is "sad" to see the records from his era and before his time continue to fall.
Still, Jackson didn't want to make Friday night all about controversy, though the undertones were unavoidably there. Here was his friend surpassing a total he has held for so many years. No matter how he feels about the choices Rodriguez has made, Jackson was able to appreciate the significance of the event for what it is -- an historic moment for baseball.
"Today is a day for me to come and tip my cap -- be a gentleman, be a fan," Jackson said. "I get a chance up close and personal to say, 'Nice going and congratulations to you. Keep hitting home runs for the Yankees. I'm rooting for you.'"