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Jordan Raanan
NEW YORK — Jameis Winston stood on top of a red double-decker bus in the middle of Manhattan with his arms extended as if the city that never sleeps was his oyster. He began belting out lines to the musical “Hamilton” with a massive smile across his face.
“It’s the Greatest City in the World! It’s the Greatest City in the World!” Winston repeated multiple times as the bus inched down 45th Street toward Broadway.
Winston, 31, in his first year with the New York Giants, stood and asked those on board for the midday journey to snap pictures of him with the Richard Rodgers Theatre and the “Hamilton” marquee in the background. He was on a tour of the city with Super Bowl winners and Giants legends Eli Manning and Shaun O’Hara for “The Eli Manning Show,” in conjunction with NYC Tourism + Conventions and the city’s 400th anniversary. This specific landmark clearly struck a chord with the quarterback who joined the Giants back in March.
Winston, known as much for his oversized personality than his on-field unpredictability — devours the culture aspect of his role more than most.
It’s almost as if he belongs in “the greatest city in the world” and was miscast elsewhere.
It’s trips like these that contributed to Winston signing a two-year deal with the Giants this past offseason. And despite rumbling that teams might inquire about his services, he’s likely to remain in New York. His contract runs through 2026 and the Giants like the idea of having a player with his skill and leadership under contract as their backup for $4 million next season.
“I think it’s just everything that this city encompasses,” Winston said of his affinity to New York. “It fits me. It’s just big. It’s broad. It’s right in your face… That’s who I am. I’m open. I’m right in your face. I’m organic, authentic, and that’s what the city is.”
It’s no wonder that the Giants and Manning approached Winston to do the tour of Manhattan on an off day during training camp last week. Not everyone would be so flexible and willing. The trio began at One World Trade Center, went past City Hall and the Canyon of Heroes — where Manning and O’Hara reminisced about the championship parades in 2008 and ’12 — drove by the Heisman office to remind Winston of when he won the award in 2013, made a stop at New York institution Joe’s Pizza, careened down Broadway, checked out Madame Tussauds and Eli’s wax figure all before finishing in Times Square where Winston had his own billboard and they celebrated New York City’s 400th anniversary with a cake from Carlo’s Bakery.
The priceless footage and banter is documented in the first episode of Season 5 of “The Eli Manning Show,” released today. It was only natural that it was the charismatic Winston who joined Manning and O’Hara on the tour. Whether it’s in the huddle, the locker room or off the field, he’s must-see entertainment.
Winston embraced it all, taking it all in like a true 2025 tourist — through his Ray Ban Meta glasses and a GoPro. It served him well, too.
“I’m so honored to be on the bus with two Super Bowl champions,” he said on multiple occasions.
“He’s kind of a natural leader. He’s going to speak his mind. But a smart guy, informed, passionate about anything he’s doing, whether it’s football, his faith, his family, his friends,” Manning told ESPN.
“I think he’s a great fit for New York because he’s been through it all. He’s been on top of the mountain, he’s had lows but he’s never lost his work ethic, his commitment, his willingness to do whatever it takes to crawl his way back, whether it’s to be a backup or starter or just be a part of the team. He’s going to be great teammate and do what he has to do.”
Therein lies the beauty of Winston. He appreciates the city and lives in the moment. But he also cares about the football. He picked the brain of Manning on everything from how he used to watched film to what he ate during the season to how he handled his off days to whether he preferred playing on turf or grass to what it was like to win in New York.
That, Winston, says, was the most memorable part. Hearing Manning and O’Hara describe what it was like coming down the Canyon of Heroes, with office paper being shredded to create homemade confetti, before finishing at City Hall to celebrate a Super Bowl triumph. Winston envisioned when he signed with the Giants.
“I would love to be a Super Bowl winning quarterback for the New York Football Giants,” he said. “And I got a chance to be that.”
Then seemingly without a care in the world Winston transformed into a young kid seeing New York for the first time.
“There’s Aladdin!”
“OMG, MSG! It pops up out of nowhere.”
“Nice building!”
“Woah, it’s Times Square!”
In reality, Winston and New York have history. He became the youngest player to win the Heisman Trophy in 2013 and stayed at the Marriott Marquis, which coincidentally was the next landmark he saw after the Richard Rodgers Theatre and “Hamilton.” He got engaged to his wife, Breion, in the Rose Room at the Metropolitan Museum of Art in Manhattan back in 2018. He took his sons to a Yankees game last year and considers being at a Knicks playoff game (Game 1 of the Eastern Conference Finals against the Indiana Pacers) as the highlight of being in New York so far.
It really is a sign that Winston has come full-circle. He was once the No. 1 overall pick by the Tampa Bay Buccaneers after winning the Heisman while at Florida State. As a reminder, he wore a white Florida State polo with mini-Seminoles plastered all over it. Now, he’s a backup for the Giants after several years in New Orleans and a one-year stay in Cleveland.
In fact, Winston was even reminded by a picture with one of the owners of Joe’s Pizza that he visited that exact spot during his Heisman weekend in 2013. Back then he was a young man on the verge of a becoming a professional football player. He’s now a husband, father and sage veteran whose voice and leadership the Giants covet in the quarterback room.
And he’s enjoying every second of the journey in the Big Apple, which he hopes is just beginning.
