Before he became one of the most decorated quarterbacks in NFL history, Tom Brady was just another multi-sport athlete trying to find his path. The world knows him for his football greatness, but at Junipero Serra High School, a young Brady stood out in baseball, too, scoring .311 with eight home runs over two varsity seasons. While destiny would eventually lead Brady to the NFL, where he built a legacy unmatched in the modern era, baseball was always close to his heart.
Brady still gets spotted with old teammates from his baseball days at times. And guess what, the old pals remember what he owes them! This time, the reminder came from another Boston legend who happened to be Brady’s old neighbour at Back Bay. The Red Sox icon, Jonathan Papelbon, was in conversation with Chris Costa in a segment of NESN when he made an interesting revelation.
“Let me tell you something about Tom. That’s some b—- he owes me a jersey. Okay. So I need you to go ahead and relay that to him. I mean. I know we used to be neighbors in Back Bay. You know, we used to live across the street from each other. I haven’t seen him since,” Pap said. And, it took no time for Costa to respond, as he came up with a promise. “I’ll tell you what, next time I see Tom, which is next week. Three Jerseys.“
What’s more, Papelbon even demanded interest from Brady for failing to keep his promise. “Tell him there’s interest on that from Pap,” he jokingly added.
Jonathan Papelbon tells Chris Costa that @TomBrady still owes him a jersey — “with interest” — from their days as neighbors in Back Bay
Unobstructed Views is presented by @BlueMoonBrewCo. When you choose a Blue Moon, everything becomes brighter! pic.twitter.com/YQis9vGqLn
— NESN (@NESN) July 10, 2025
But for what does Brady owe Papelbon a jersey? We don’t have a clue about it, but it might be a bet Brady lost to Papelbon, who knows? Whatever it might be, it was a rather hilarious gesture from Papelbon to remind Brady about what he owes. And why not? It was all good fun. A little bit of banter does not harm anyone. Fans would now wait for Brady’s response after Papelbon put in the reminder.
For those unaware, Tom Brady and Jonathan Papelbon are two of the biggest names in the Boston sporting landscape. While Papelbon played a key role in the Red Sox’s 2007 World Series win, Brady was the face of the Patriots from 2000 to 2019, leading them to six Super Bowl titles. So, both have brought plenty of championship glory to Boston. And hey, Tom Brady’s connection with the Red Sox is nothing new.
Brady and the Red Sox: A good ol’ relationship
Tom Brady has been spotted at Fenway Park multiple times over the years, often attending games and cheering for the Red Sox. And his presence has always been a fan magnet, drawing attention whenever he’s in the stands. Back in 2017, the Red Sox even honored Brady, inviting him to throw out the first pitch on Opening Day.
Then, in 2018, Brady publicly backed the Red Sox to win the World Series. “It’s going to be a lot of fun to watch. It’s been a while since they’ve been to the World Series, but everyone’s paying attention, everyone’s following them, they’ve had an incredible season, and we’re all cheering them on. It’s going to be pretty sweet,” he said on WEEI. And, sure enough, the Red Sox did just that, beating the Dodgers and claiming their ninth title.
So, even though Brady made his name on the football field, his bond with the Red Sox and the city’s baseball culture shows just how tightly woven Boston’s sports community really is.
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