And then he was asked what it would be like to trot out onto the Yankee Stadium diamond for the first time since the deaths of George Steinbrenner and Bob Sheppard. The man they call "Mr. October" and the infamous "straw that stirred the drink" paused a bit longer this time, and the eyes that had teetered on the brink of tears finally, for a second, careened over it.
"I'd rather not be here for that," Jackson said candidly. "I'd rather have passed."
Jackson knew he needed to be at Old-Timers' Day, and not just because it's part of his contract -- as general manager Brian Cashman playfully pointed out. There is perhaps no other player who better epitomized the complicated, chaotic, but ultimately respectful relationships Steinbrenner forged with his players.
Jackson was emotional throughout a 20-minute press conference, remembering the owner that was part-father, part-foe, and the announcer he once dubbed "the voice of God."
Along with Steinbrenner and manager Billy Martin, Jackson was a constitutive element of the infamous Bronx Zoo in the 1970s, the trio frequently sparring among one another and vying for the attention of the ever-hungry New York media. But Jackson claimed he and Steinbrenner were never enemies; their relationship may have been complicated and contentious, but it was never regrettable.
"There was always respect," Jackson said. "If I had any difficult times with him, it was because I was in a learning process of understanding life."
Jackson understands that he and Steinbrenner will forever be linked. It was Steinbrenner who brought him to New York with a $2.96 million contract -- lucrative by the standards of 1977 -- and it was Steinbrenner who gave him a role on the New York stage -- one he responded to with a starring performance. Jackson knew that, much like the Frank Sinatra lyric, if you could make it under Steinbrenner, you could make it anywhere.
"There are players and owners in history that are tied together in this sport, and I'm proud to be tied to him," Jackson said. "That'll never change."
That bond is what made Tuesday such a difficult day for Jackson, who heard about Steinbrenner's death while he was in Anaheim for the All-Star Game. The owner's passing at the age of 80 surprised Jackson.
"I had just spoken to him on his birthday," Jackson said, mentioning that he and Steinbrenner had talked a lot over the phone during the past few months. "Certainly I knew the health wasn't the same, I knew the strength wasn't there, but the conversations were so good for so many months. I think I was caught off-guard when I heard.
"I got quiet, pensive. I was lucky I was around close friends."
Jackson eschewed some media appearances at the All-Star Game, not sure he could hold himself together. Even after a few days of reflection, the emotional impact of Steinbrenner's and Sheppard's deaths manifested itself in a voice that occasionally quivered and eyes that often stared placidly in the distance.
"He's meant so much to so many people," Jackson said of Steinbrenner. "His drive, presence, character and personality have permeated the organization, the city and certainly the game of baseball, as well."
Jackson did smile more when discussing Sheppard, whom he compared to late UCLA coach John Wooden. Wooden and Sheppard, born six days apart in October 1910, both died this summer at the age of 99.
"What stands out to me about both of them is you always felt better when they were around you," Jackson said. "Their concern for their fellow man, their family and God was on their chest. It was a grace that I had tremendous admiration for."
Jackson enlisted Sheppard's help with his Hall of Fame speech, and he recalled winning a quarter from him when he talked for less than two minutes when the Yankees retired his No. 44.
"If they ever did a movie about God and they needed a voice, it would be Bob Sheppard," Jackson said. "That's something we will always love and cherish and will be a part of the Yankees' organization forever."
Tim Britton is an associate reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.