In 1999, Jackson was rated by Baseball America as the best 12-year-old baseball player in the country. That same year, the righty was approached by a scout from the Yankees after hitting three home runs in a 14-year-old league.
"He gave me his card and told me he'd come out to a couple more ballgames because his son played in the same area," Jackson said. "He told me he'd keep in touch and to call if I had any questions, which I don't know what kind of questions a 12-year-old would have at that age."
The Texas native's encounter with the scout didn't let it affect him mentally and, despite being approached by the Yankees -- who were in the midst of winning their third World Series title in four years -- he was still just a kid.
"I think age has something to do with it," Jackson said. "If I had been a freshman in high school and approached by him, it would have been different. At the age I was at, I was not mature enough to know what any of it meant or that I could possibly play for the team one day. I was excited for the moment, but after that it was just like any other thing at 12 years old."
Jackson's parents always made sure to keep their son focused, they even built him a batting cage in their backyard so he could work on his swing. Despite the hype surrounding him, he wasn't even a teenager yet.
"They cared more about my grades first," Jackson said. "They kept my head on my shoulders. They wouldn't let me get a big head if I started to ever get one. They would let me know and bring me back down to Earth real quick."
Ten years later, the 22-year-old is now Baseball America's No. 1-ranked prospect in the Yankees' system. In 2008 at Double-A Trenton, Jackson hit .285 with nine homers and 69 RBIs while swiping 19 bases to help improve his prospect status. He was named the Eastern League postseason MVP after going 6-for-16 with a homer and five RBIs.
"I always envisioned myself in situations like this," said Jackson. "It's what always made me want to get to the Major League level, thinking about what it would be like when I get to my ultimate goal. I think about that and hope that I can one day reach it."
When exactly that day will come is still uncertain, but Jackson tries not to concern himself with the Yankees' timetable.
"I try to always stay consistent and keep my eye on my goal," Jackson said. "Talking to players and coaches that are there or have been there let you know that all the work will pay off. It's not going to be easy. They just let me know that once you make it, you still have to work hard and, in the end, it will all pay off."
A lifelong baseball fan, the 6-foot-1, 185-pounder grew up watching his favorite player, Ken Griffey Jr., roam center field, Jackson wanted to be like and hit like Griffey. Jackson is athletic and a smart base runner with very good range in center with a strong and accurate arm, much like Griffey was in his early days. The power numbers aren't yet there, but as Jackson matures, he will likely put up solid numbers.
"As you move up in levels of the sport you play, players are going to be better, bigger and stronger," Jackson said. "So you've got to work hard and always be doing something to improve."
So far this season at Triple-A Scranton/Wilkes Barre, Jackson is hitting .311 with four homers, 38 RBIs and is 17-for-19 in stolen base attempts.
Jackson still needs to improve on his plate discipline -- through 92 games, he has already struck out 89 times.
"You have some guys up there now who made it based on natural talent and for the rest of us, it takes a little bit more work," Jackson said. "You can be going good for a long time, then all of a sudden you meet people in the sport you play who are just as good, if not better. You have to keep working hard to try and better your game."
Jackson was a two-sport star until he turned professional as a baseball player. He committed to play baseball and basketball at Georgia Tech when he was in high school, but decided to sign with the Yankees for $800,000 after getting drafted in the eighth round by the Bombers in 2005.
"I think if I had taken the other route then it would have been a lot harder juggling two sports, my grades and college, where you don't have anyone telling you to do your work," Jackson laughed. "I think I definitely made the right choice and I am happy to be where I am today."
Jackson's athleticism and work ethic has allowed him to blossum into the player he is today, a call away from the Bronx. He has played Hawaii Winter Baseball and in the prestigious Arizona Fall League, where he earned a spot on the AFL All-Prospect Team. Jackson is motivated to do whatever it takes to make it to the Majors and doesn't want to take any breaks in getting there.
"I really don't want to," Jackson said. "If I have a bat in my hand, then I am satisfied. If working on my skills is what it's going to take to get to my goal, then I'm going to play year-round."