But it wasn't until three years ago, that he actually made his dream a reality.
He bought his first bike and began practicing at the motocross track right down the street from where he lives in Kahuku.
Now at the age of 39, he's proving just how far he's come at this week's National Championships in Tennessee.
"Well it really means a lot, last year, I was in qualifying position in the second qualifier and I ended up crashing and just so little people make it into the event out of the amount that enters, and it's just really an honor", said Kress.
Kress qualified for the National Championships after placing in the top 5 in two qualifying races in California.
To give himself a better chance of winning, Kress is competing in two divisions at the Nationals, the 25-and-over and 35-and-over age groups.
"I'd really like to get into the top 10 and just show everyone in the mainland that we really got good riders out here in Hawaii, there's so many young kids who just haven't been recognized yet, and I'm just a small tiny part of the talent that's here", explains Kress.
Kress is aware of the serious risks associated with motocross, but says he's been very lucky to avoid any major injuries.
"Riding is really dangerous, it can all end in an instant, I have broken both feet, I've dislocated my shoulder, broke some of my fingers, but actually that's really getting away easy with this sport it can really bite you", said Kress.
Right now, James isn't thinking about the dangers, he's only focused on racing and representing the state of Hawaii.