Tom Brady, Leonardo DiCaprio pictured together in Italy as NFL fans discuss wild theories - "Nightmare blunt rotation"

Tom Brady and Leonardo DiCaprio were on the same yacht in Sardinia, Italy, to celebrate entrepreneur Bert Hedaya's birthday. Restaurant mogul David Grutman shared a photo of the guests via Instagram Stories.

Tom Brady and Leonardo DiCaprio were just some of the guests during Bert Hedaya's birthday celebration in Italy. (Image credit: Instagram.com/davidgrutman)

Members of the Fauxmoi Reddit community picked up the post, leading to the following comments.

Comment by u/frecklebb3 from discussion So Tom Brady and Leo hang out on yachts in Italy together now? I feel that might be awkward. in Fauxmoi

Comment by u/afterthoughtname from discussion So Tom Brady and Leo hang out on yachts in Italy together now? I feel that might be awkward. in Fauxmoi

Comment by u/la-escorpiona from discussion So Tom Brady and Leo hang out on yachts in Italy together now? I feel that might be awkward. in Fauxmoi

Comment by u/Ok_Yogurtcloset802 from discussion So Tom Brady and Leo hang out on yachts in Italy together now? I feel that might be awkward. in Fauxmoi

Comment by u/youhadabajablast from discussion So Tom Brady and Leo hang out on yachts in Italy together now? I feel that might be awkward. in Fauxmoi

Comment by u/DifficultNecessary10 from discussion So Tom Brady and Leo hang out on yachts in Italy together now? I feel that might be awkward. in Fauxmoi

Comment by u/Exciting_Potato_6717 from discussion So Tom Brady and Leo hang out on yachts in Italy together now? I feel that might be awkward. in Fauxmoi

Comment by u/_Democracy_ from discussion So Tom Brady and Leo hang out on yachts in Italy together now? I feel that might be awkward. in Fauxmoi

While it's unknown if Brady and DiCaprio shared a conversation during the party, the last comment reiterated the awful link between the seven-time Super Bowl winner and the multi-awarded actor.

DiCaprio dated Brazilian supermodel Gisele Bundchen from 1999 to 2005. A year later, Bundchen and Tom Brady started dating. They married in 2009 and had two kids: Benjamin Rein and Vivian Lake. In October 2022, Brady and Bundchen finalized their divorce after a 13-year marriage.

Bundchen isn't slowing down on fashion commitments after their breakup. She attended the 2023 Met Gala alone and took on more modeling projects. Recently, Bundchen worked with brands like Louis Vuitton, Versace, and Arezzo.

Meanwhile, Leonardo DiCaprio dated Israeli model Bar Refaeli from 2005 to 2011. He also dated Toni Garrn from 2013 to 2014 and actress Camila Morrone from 2017 to 2022. The one-time Academy Award for Best Actor winner is rumored to be currently dating Gigi Hadid.

Aside from Hedaya's birthday, DiCaprio was in Europe to promote Killers of the Flower Moon, a movie he starred in and co-produced with Martin Scorsese. The movie premiered at the Cannes Film Festival earlier this month.

Grutman, DiCaprio, and Brady were also part of the star-studded guest list for the $12.9 million wedding of Joe Nahmad and model Madison Headrick.

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Tom Brady is starting to build his business empire

When he's not attending special occasions or spending time with his family, Brady is investing his money from playing football and multiple endorsements.

He purchased a minority ownership stake in the Las Vegas Raiders, ending rumors of playing football once again.

Brady is also a minority owner of the defending WNBA champions Las Vegas Aces, announcing his newest venture via Twitter.

Brady's growing business interests include TB12 Sports and the Brady Brand clothing line. He also invested in the NFT platform Autograph and media company 199 Productions. He also raised $50 million for Religion of Sports last November.

Tom Brady also has a ten-year, $375 million contract with FOX Sports as their lead color commentator during NFL broadcasts. He was supposed to join the panel this year but decided to take a back seat and commence his new role in 2024.