Julian Edelman never liked Peyton Manning. Not back in his playing days. Not even before he made it to the NFL. On a 2024 episode of the Games with Names podcast, Jules let it rip: “I never liked Peyton Manning. He was always the guy… the best guy in high school, college, his dad was a pro. He was the guy, and he was a f—ing stud.” Translation: Too perfect. Too polished. And Edelman? He rode with Tom Brady, instead. A fellow Bay Area underdog. The guy who wasn’t supposed to be great—until he was.

So what changed? Fast-forward a year, and the same Julian Edelman was on Instagram, posing with Manning and Rob Gronkowski for Tiffany & Co.—yes, the jewelry brand behind the actual Lombardi Trophy. The trio, who’ve combined for 11 Super Bowl rings, are now starring in an ad campaign that, well, hits a little close to home. Edelman’s caption? “Playing the field. Sorry @tombrady.” That’s right. Two of Brady’s ride-or-die guys are now teaming up with the same QB he used to go toe-to-toe with every January.

But how’d we get here? Start with Manning. Earlier in the season, he joked that Brady and Gronk owed him royalties for ripping one of his signature plays. On ESPN’s The Breakdown, he told Bill Belichick, “They should’ve sent me a check every time they ran that play.” Belichick didn’t deny it. He laughed. “You’re right, Peyton. We did take it from you.”

That ‘trap pass’—a misdirection that left linebackers dazed and Gronk wide open—was a staple in New England. Manning claimed it. Belichick credited it. Brady and Gronk? They didn’t argue. They just hit the comment section. “Checks in the mail,” Brady quipped.

Meanwhile, now that play might have helped build a dynasty. But this Tiffany collab? That’s just three legends flexing some off-field chemistry. Funny enough, it also gives Gronk a full-circle moment with the Lombardi. Remember when he dented it after a Red Sox pitch from Edelman? Yeah, that very trophy. As for Peyton, no dents—just two rings, a ton of shade, and now… a surprising bromance. So, sorry Tom. Your guys just signed a brand deal with your old nemesis.

Peyton Manning was, indeed, Tom Brady’s biggest headache

Remember back in February 2025, when Peyton Manning hopped on Instagram and dropped a bomb: a full-blown Colts reunion, celebrating their Super Bowl XLI run? Peyton captioned that post: “Getting the band back together in Indy next week,” he wrote. For Colts fans, pure nostalgia. As for one Tom Brady? A little trauma. The man himself jumped into the comments with, “That group still gives me nightmares.”

To be fair, Brady wasn’t just playing for laughs. That rivalry lived in AFC Championship weekends and dictated playoff seedings. Colts vs. Patriots wasn’t just good football, but look at it as the war chess of the TB12 & PM18 era. Each game wasn’t just a win or loss; it was a vote on legacy. And now, years later, a Colts reunion still has Brady checking under the bed.

But Manning’s reunion tour was more than a meet-and-greet. He was pulling together names that still echoed in Brady’s stat sheet nightmares. Names like Coach Tony Dungy, Jeff Saturday, and the rest of Indy’s 2006 Super Bowl squad. “We’ll discuss the greatest plays and most memorable moments from the Super Bowl run,” Manning promised in a video on Omaha Productions. And yes, he teased some good old yelling with Saturday for tradition’s sake. It’s not just a reunion; it’s a reminder that that Colts team got theirs, and Tom Brady remembers it.

Meanwhile, here’s the stat that ties it up with a bow: Brady led the head-to-head, 11-6. But Manning’s Colts ruined a few perfect dreams, especially in 2006. That year, Manning finally got over the hump, and Brady? He was watching the Super Bowl from home. For a guy who never forgets a loss, it’s no wonder that blue horseshoe still haunts him.