So now, with the benefit of hindsight, what would he tell his 18-year-old self?
"I was on Twitter and I was scrolling -- actually my trainer sent me a clip of Steve Harvey talking about what he would do back in the day and how your early years end up reflecting on your later years," Winston said as the inaugural guest on NFL Network's Good Morning Football. "So now I'm trying to mature, be a better person every single day. I realize that your early years are always going to show you where you'll end up in your later years."
Winston was also asked what type of advice he would give 2016 No. 1 pick Jared Goff. Winston, despite his checkered past, earned praise in Tampa Bay for a social fearlessness inside the locker room. He bucked the trend of typically timid rookie quarterbacks and is looked at as a potential leader for the franchise going forward. How does Goff follow in his footsteps?
"You gotta know your place, but you gotta be yourself," Winston said. "Who you are is very important because these guys know -- real recognizes real, so you can't go around trying to be fake to anybody. You have to show up and show out and your actions speak louder than words. Go out there and produce and be kind to your teammates -- Jared Goff is a great quarterback so I know he's going to do good."
Winston did and said all of the right things last season, even if that might never be enough to repair his public image. In the sometimes-insular NFL world, a player is only as good as his last game and Winston has some lofty expectations to live up to once again in 2016. Luckily, he understands the importance of these early years and how they might affect him as a player and a person down the road.