And when it came time to answer questions from the media on Friday, the Florida State star quarterback did so confidently and without hesitation, even when his protection broke down.
Winston and four of the other six Heisman finalists — Texas A&M's Johnny Manziel, Auburn's Tre Mason, Boston College's Andre Williams and Northern Illinois' Jordan Lynch — met with reporters at a Midtown Manhattan hotel for short interviews. Alabama's AJ McCarron was in Baltimore accepting another award.
Florida State officials tried to limit questions that were even vaguely related to the rape accusation against Winston. The state attorney closed the investigation last week, saying there was not enough evidence to win a conviction.
The 19-year-old, who hasn't spoken directly about the details of the investigation, seemed unfazed by the questions that did come his way. He said he was fine remaining silent about the case.
"I knew I did nothing wrong. I knew I could respect the process and I'd eventually be vindicated. It was more about me being silent for my family because I didn't want to put my family in those situations.
"We had so much respect for Mr. (Tim) Jansen and everything going around and knew I did nothing wrong and everything would be OK."
Winston was the only Heisman finalist to show up with his lawyer, Jansen, who strolled in with the Florida State entourage for the media availability. Winston looked like a college student going to class: Black Florida State sweatsuit with garnet trim, and a matching backpack hanging off his shoulders.
Winston is the overwhelming favourite to win the Heisman after a sensational season, leading No. 1 Florida State to the national championship game against No. 2 Auburn.
But the celebration of his record-breaking performance has been muted by a year-old sexual assault allegation that went from dormant to active last month. The Tallahassee Police gave its finding to prosecutors, who took three weeks to investigate further and decide not to press charges.
Documents and reports, including the accuser's accounts to police, have been made public. They are less-than-flattering to Winston.
On Friday, the accuser's attorney, Patricia Carroll, asked Florida's attorney general to independently examine the rape investigation, claiming it was riddled with problems.
A few hours later, Winston was taking questions, mostly about football and the Heisman and being in New York city for the first time.
He was asked about dealing with "off-field issues" and two other questions that were indirectly related to the investigation.
"It was stressful, but you've got to look forward," he said.
Soon after, Florida State sports information director Kerwin Lonzo said: "He's only answering football questions and about the Heisman. Move on."
Winston then left the media session too soon. Each finalist was supposed to rotate through three tables of reporters. Winston came back for a second session and Florida State spokesman Elliott Finebloom apologized for the miscommunication.
Winston said he had yet to work on an acceptance speech, talked about how he and his mom took Mason out to dinner on Thursday night in Florida, when both were at the ESPN's college football awards show, and how he worked as a scout-team version of Lynch when the Seminoles were preparing to play Northern Illinois in the Orange Bowl last season.
Winston would be the second straight freshman to win the award after Manziel last year, and he'd be the third Florida State player — the first since Chris Weinke in 2000.
What can he do for an encore next year?
"Hopefully," he said, "I can do it over and over again."