He won the 200-meter - and that was the beginning for the 6-foot-5 sprinter, who had never been away from his parents or his modest village of Sherwood Content in Trelawny Parish before he left for Kingston to train professionally.
At 12, when he earned a scholarship to attend a high school known for turning out strong athletes, it all clicked for Jennifer. Bolt loved cricket and soccer growing up, but he has said he settled on track because he was good at it.
"He could not keep still when he was a child," said Jennifer. "Even in the bed, you could see him tossing. When he started high school, that's when we saw that he's really competitive."
Over the years, Jennifer said, she has realized her best approach is to remain strong when her son falters.
"I've learned to cope with it. I cannot feel down when I have to support him. I just pray and hope that everything will be good," she said.
"I know that he still depends on his mother."
Just as he did as a teen.
"I can remember in 2002, the world championships. At the time he was 15 and before the games he didn't want to go. He cried, and I had to try to comfort him, encourage him to go out and do his best because he didn't feel that he could have done it," she said. "I was really, really nervous. My legs were shaking and my heart beat fast."
Then she listened to the crowd.
"The crowd was behind him. From then I didn't feel that nervous," she said.