The kid was still polishing his skills in NASCAR's minor leagues in 1998 when his old man finally won, and Junior had seen the elder Earnhardt suffer through close call after close call in the biggest stock car race of them all.
That isn't going to happen to Little E. He's the Daytona 500 champion.
"I've seen it lost so many times by my dad over and over," Junior said in the emotional moments after winning the Great American Race on Sunday. "I was taught so many lessons about this place ... Now I don't have to worry about it any more."
For 19 years, Dale Sr. charged at Daytona as only the Intimidator could. And for 19 years, the famed Daytona International Speedway oval denied him victory.
He won 33 other events here, dominating year after year in the 500 only to see it wrested away by an accident, a broken part, a car that was just a little faster at the end or something even more frustrating.
Once, the elder Earnhardt was within two miles of winning the 500 in a runaway when he ran over a piece of metal from another car, tore up a tire and went home unhappy - again.
He rarely showed much emotion, but Junior could see how hard his father took leaving here each February without a victory.
"That ate the man's insides out," he said. "Inside of me, back then, just a little bit of wanting to win this race started up. You know it's been building ever since... I'll be honest with you, this is more important to me than anything, any other race I run all year."
Little E seemed to inherit the legacy of losing this race when his father died in a last-lap crash in the 2001 Daytona 500.
Since his father's death, Junior had won seven races on the two and half mile-long oval - but not the big one.
He finished second to Dale Earnhardt Inc. teammate Michael Waltrip in that fateful 2001 race and was favored the next year, but got caught up in a big crash and wound up 29th.
Last year, Earnhardt Jr. was the heavy favorite after winning the Budweiser Shootout, taking the outside of the front row for the 500 in time trials, winning one of the 125-mile qualifying races and taking the checkered flag in the Busch Series race the day before the 500.
But, on the big day, a broken alternator cost him a lap. And when rain ended the race 91 laps short, Waltrip was the winner again with Little E a disheartening 36th.
Only four years into his career, he was already hearing the question his father had to answer for so many years: "Are you ever going to win the Daytona 500?"
"Good God, I'm the Daytona 500 champion," Junior said Sunday after he passed Tony Stewart for the lead with no drafting help and went on to the most popular NASCAR victory since his father won the big one exactly six years earlier.
Dale Jr. said he felt like his father rode along with him.
"He was over on the passenger side with me," he said. "I'm sure he was having a blast."
It seemed like everyone was happy for Earnhardt - even his fiercest competitor.
"I think his father's really proud today," said Stewart, who tried every way he knew how to get back past Little E's No. 8 Chevrolet. "If I could have held him off, had him finish second, I would have done it in a heartbeat.
"But there was no holding that kid back today."
And NASCAR could hardly have asked for more.
It's just too bad President Bush left halfway through the race. He missed some great racing.
On the day that the Nextel Cup era officially began, real racing returned to Daytona, with drivers able to run side by side and pass and hardly a word about restrictor plate racing or the much-feared tire problems.
Instead, 180,000 people celebrated with the jubilant Dale Jr., roaring their approval as he slowly rolled to a stop at the finish line, popped out of the car, punching the air with his fists, then leaped into the arms of his crew who dashed across the infield grass to be part of the moment.
Junior has rarely avoided a party in his 29 years and Sunday was going to be a real big one - until he was reminded he still has some work to do at Daytona.
Rain on Saturday interrupted the Hershey's Kisses 300 Busch Series race with Junior leading. It was scheduled to resume Monday morning.
"That's going to be hard," Earnhardt said, grinning. "I'd like to enjoy this one for a while. They may have to put the whip to me. I'll probably be pretty laid back."
By Mike Harris