The five-star quarterback from Hueytown (Ala.) High has been a Florida State commit for months. But as National Signing Day came - and went - Wednesday, the No. 10 overall recruit in the country still hadn't made up his mind.
He has been feeling a pull toward Stanford lately. And it's hard to blame him.
There is the school's outstanding academic reputation and a chance potentially to play his other love, baseball, in one of the top college conferences.
And now this: Perhaps the greatest collection of offensive line recruits ever.
While Winston couldn't make up his mind - he is expected to choose between the Gulf Coast and the West Coast Friday - Stanford reeled in an offensive line class that includes two five-star players, three members of the Rivals100 and five members of the Rivals 250.
Rivals.com national analyst Mike Farrell thinks it's the best collection of line recruits he's seen in more than a decade in the business.
"Stanford's offensive line class on paper is the best since we have been ranking prospects at Rivals.com," he said. "The closest class to this one would be USC's haul in 2008, when they got Matt Kalil, Tyron Smith and Khaled Holmes.
"This Stanford class will have to be pretty good to live up to the USC class of 2008, but on paper, it has more potential."
Five-star tackle recruits Kyle Murphy of San Clemente (Calif.) High (No. 3 tackle) and Andrus Peat of Tempe (Ariz.) Corona Del Sol (No. 6) head the list. They are joined by four-star players Graham Shuler of Brentwood (Tenn.) Brentwood Academy and Nick Davidson of Eden Prairie (Minn.) High.
"[The coaches] had a conversation last spring that I'll never forget," he said on signing day. "The comment was made in the room that this could potentially be one of the best offensive line classes in modern football history.
"It's just the combination of size, athletic ability, toughness ... it's rare that you get that many guys that can play this well."
But where will they all play? Farrell doesn't think that will be a problem.
"The two five-stars, Andrus Peat and Kyle Murphy, are potential first-rounders, and each could play left tackle in college. So I expect them to be either bookends or for Murphy to slide inside and for Stanford to use them on the same side of the line and dominate," he said. "Joshua Garnett is just shy of five-star status, and I think he'll be an incredible guard, as will Graham Shuler, who could also snap center if needed. Brandon Fanaika is a top interior guy and Nick Davidson can play tackle or guard.
"Johnny Caspers gets overshadowed by this group, but he's mean and nasty and could surprise a lot of people."
What would surprise people is if Winston actually chooses Stanford. He's considered a strong lean to the Seminoles.
Stanford, which has been to consecutive BCS bowls, feels it can reach that level of sustained success.
The school survived the loss of head coach Jim Harbaugh after last season. And now the Cardinal are in position to survive the loss of the projected No. 1 overall NFL pick, quarterback Andrew Luck, thanks to a class ranked No. 5 overall by Rivals.com. A class that isn't all offensive linemen.
The group also is solid on defense, as it includes the No. 3 defensive end (five-star Aziz Shittu), No. 3 cornerback (four-star Alex Carter) and No. 4 outside linebacker (four-star Noor Davis).
The class is so deep that four-star running back Barry Sanders, the talented son of the NFL Hall of Famer, is not even a headliner.
The key for Stanford, Rivals.com West Coast analyst Adam Gorney said, is keeping up the pace. The Cardinal's highest-ranked class before this one was No. 20 in 2009.
"This is a great class, one of the best in school history," Gorney said. "But it's last year's class. Recruiting for next year starts today. Stanford needs to show it can keep it up every year."
It certainly has a solid start - especially along the offensive line.