He'll find out whether his dream becomes a reality on Saturday night. The redshirt freshman quarterback is one of six finalists up for the most prestigious individual award in college football.
Winston and his high school coach Matt Scott were in Tuscaloosa on a recruiting trip at Alabama when he took a picture with Mark Ingram's 2009 trophy. He wanted to be the first at Alabama to win the award, at the time.
"When Ingram won it I was just like, 'Well, he won it. So, I've got to be the next person from Alabama to win it," said Winston, who pointed out that Ingram is actually from Michigan.
"Football is so important to Alabama, so any time you have a national achievement it means a lot to your state and your family," Winston said. "You always dream. You've got to dream big because if you don't dream big, there's no use to dream at all."
He'll be joined in New York by Texas A&M's reigning Heisman winner Johnny Manziel, Alabama's A.J. McCarron, Boston College's Andre Williams, Northern Illinois' Jordan Lynch and Auburn's Tre Mason.
Winston set Atlantic Coast Conference freshman records for the most yards passing (3,820) and touchdown passes (38) while leading the No. 1-ranked Seminoles to a 13-0 record and berth in the BCS championship game.
Florida State and Winston continued to excel despite a sexual assault investigation that became public last month. The State Attorney's Office announced that it would not press charges against Winston last week. However, Winston's legal problems may not be over. The accuser, her lawyer and family have scheduled a press conference Friday.
There is no doubt about Winston's talent. He is already being talked about as a potential franchise quarterback in the NFL, even though he can't be drafted until 2015.
"The one thing that you don't know about a lot of players is how well, how quickly they're able to read defenses," said Gil Brandt, NFL draft analyst. "Once you get into the NFL, reading defenses is paramount. Are you going to be able to do it as quickly as you have at the college level?"
Brandt helped build the Super Bowl-winning Dallas Cowboys as vice president of player personnel from 1960-89. He said Winston has steadily improved and his accuracy is one of his most valuable traits. His 67.9 completion percentage is tied for 10th best in the country. Florida State coach Jimbo Fisher has lauded Winston's ability to take what the defense gives and throw to the open receiver.
Brandt said the way Winston dealt with the accusation and the subsequent media coverage is a positive.
"That speaks well from the standpoint of concentration," Brandt said. "And I think the most important thing for success to a football player is concentration."
As well as Winston has played, there's room to improve. Brandt pointed out mechanics of his throwing motion and the movement of his hips. Brandt wants to see incremental improvements across the board during Winston's sophomore season — completion percentage, the way he adjust plays at the line of scrimmage, game management.
Scott said he and Winston's family purposely tried to prepare him for celebrity in high school by exposing him to media and events across the country. None of that compared to this season and the coverage of the investigation. That attention will only increase if Winston wins the Heisman. He's likely to be in the running again in 2014.
"It was different to go from such a slow, small type of small town College Station status where everybody knows you and people run into you, then to take that to a national level where you walk around Times Square and people are running into you and noticing you," said Manziel, who endured his share of controversy after winning the award in 2012. "Just how big things boomed and spread out across the entire country, world, everything after that was nothing like I expected."
Seven years ago Winston was first introduced to the Heisman through the NCAA Football '06 video game. He was 13 years old, created himself on the game and won the award. Winston could match his digital persona Saturday.
"He's definitely the truth," said 1993 Heisman winner Charlie Ward, who regularly texts Winston. "He's the real deal. His attitude toward getting better and not settling for his last accomplishments is great.
"It was impressive to see him come out and do the things that he's been able to do as a younger guy."