The Big Lead

Tom Brady elevates legend status 'chatting up' Sydney Sweeney at Jeff Bezos wedding

NFL legend Tom Brady spent some time in Venice for the $50 million Jeff Bezos-Lauren Sanchez wedding, and reportedly spent time "chatting up" Sydney Sweeney.

By Josh Sanchez

Tom Brady walks the red carpet on Sunday, May 25, 2025, ahead of the 109th running of the Indianapolis 500.
Tom Brady walks the red carpet on Sunday, May 25, 2025, ahead of the 109th running of the Indianapolis 500. / Michelle Pemberton-USA TODAY Network via Imagn Images
facebooktwitter

Future Pro Football Hall of Famer Tom Brady is firmly in the NFL quarterback GOAT conversation. But the man seems to be good at most things.

He has his own flaws in the broadcasting booth with FOX Sports, but in his other off-field ventures he has a dating roladex that rivals MLB icon Derek Jeter. And that may be expanding.

Brady has been in Venice for the wedding of Amazon founder Jeff Bezos and Lauren Sanchez, which cost approximately $50 million.

MORE: Tom Brady, Orlando Bloom arrive for Jeff Bezos' $50 million wedding

Another guest was the one and only Sydney Sweeney, who always captures the internet by storm. According to TMZ Sports, Brady has been working some game in Venice and "chatting up" the popular actress.

"Sources who are there tell us Tom, Leo, Orlando, Sydney, Jerry Seinfeld, Oprah, Charissa Thompson and the Kardashians are all staying at the Gritti ... and Sydney is the "center of attention" for single guys, including TB12," TMZ writes.

"We're told the gang's been hanging at the hotel bar, partying and dancing ... and Tom is taking center stage as the life of the party -- even spending some time chatting up Sydney, who one source described as 'f***ing beautiful' in person."

MORE: Eli Manning gets best of Tom Brady again after wild WWE entrance at Fanatics Fest

Shoot your shot, TB12.

Tom Brady is 47 years old and Sweeney is 27, so the Super Bowl-winning signal-caller still has a long way to go before he is following in the footsteps of his former head coach Bill Belichick and Jordon Hudson.

Bill Belichick and Jordon Hudson on the red carpet before Super Bowl LIX NFL Honors at Saenger Theatre.
Bill Belichick and Jordon Hudson on the red carpet before Super Bowl LIX NFL Honors at Saenger Theatre. / Kirby Lee-Imagn Images

GET MORE TOP STORIES from The Big Lead by subscribing to TBL YouTube channel

ROUNDUP: Flagg Day, 'entitled' prospects, MLB All-Star finalists, and more

MLB: Tributes pour in as MLB's oldest manager goes on medical leave for rest of 2025 season

MMA: UFC 317 weigh-in results: Ilia Topuria vs. Charles Oliveira official

SPORTS MEDIA: Kendrick Perkins slams Bill Simmons after ESPN criticism

VIRAL: Trail Blazers rookie reveals life off court as anti-social dream

Home/Sports Media