Now he's preparing for his 50th season in professional baseball, and the memories are much fresher. If he can get this team through that last postseason step, he'll have one more memory that will trump all the others.
He would have a World Series title with the team that gave him his chance as a player a half-century ago, then as a Minor League manager after that. It's the same team that brought him back for the long-awaited chance to manage in Detroit six years ago.
He's the longest-tenured Tigers manager since Sparky Anderson, and he's climbing the team's all-time wins list quickly. A championship would put him with Anderson and Tony La Russa as managers to win World Series titles with teams from both leagues. More important, it would entrench Leyland's place in Tigers history, and it would give him the reward at the end for all the second-guessing, all the doubts he has seen and heard in recent years.
He's not promising anything. After last year's path to the Fall Classic, he's not taking anything for granted, either.
"When you start from scratch, new year, I don't know who the team to beat is," Leyland said. "Hopefully, it's the Tigers."
Not only does his place in Tigers history seem to be riding on how he fares, so does his place in Tigers present. When nothing up ahead is certain, it's hard to spend much time looking back.
Until the Tigers pulled away with the American League Central, eventually clinching with two days to go in the regular season, they were on the verge of a big disappointment. They came into the season with championship dreams fueled by January's signing of Prince Fielder, and they only increased as Spring Training went on.
They didn't take over the division lead from the upstart White Sox until mid-September, and they had to make up a three-game deficit with 16 games left to do it. Leyland had nothing guaranteeing he would survive the firestorm if they missed the playoffs. All he had was a one-year contract that expired at season's end, whenever that end came.
After all was said and done in October, Leyland got the contract extension he wanted. He also got the versatile right-handed hitter, Torii Hunter, that his team badly needed in the World Series.
Nevertheless, with another one-year deal, he could be facing much the same scrutiny, like a cycle.
He's fine with it, he insists. If he's going to take his situation year to year, as he has, he has no problem with the club doing it. He feels good and he wants to manage beyond this coming season, but he has problem not guaranteeing it.
"We've got a good situation," Leyland said. "I took a pretty good beating this summer and rightfully so. I think the one-year deal is fair for everybody. They can make a decision whether they want to bring me back, and if at the end I'm tired of it, I can say so long.
"I don't know [management] anything, and they don't owe me anything. It's all good. It puts a little pressure on me during the season."
Given the speculation, it was more than a little.
"You hear the rumblings," Leyland continued, "not from the organization, but a lot of fans who wanted me fired during the season. That's just part of it. You have to accept that. I'm willing to accept that doing a one-year deal. I don't want a two- or three-year deal, and I doubt they'd want to give me one. I think it works out good because I trust the organization and I also trust my own ability.
"I think I'll do good enough to maybe get another contract for a year. I think I'll do good enough to do that. If I don't, that's fine. They should get somebody else. That's the way I look at it."
It's the same year-to-year approach his good friend La Russa took during his final years managing the Cardinals. He retired a year ago off a World Series victory. If the Tigers won next fall, ending Leyland's 50th season in baseball with a title, the timing would be impressive, whether Leyland walked away or not.
Either way, the man who claims he was voted most popular in his high-school class would have a new popularity in town. He has always been popular in Perrysburg.
"I could bring out my yearbook for you if you don't believe me," Leyland said.