NFL superstar Tom Brady recently gave fans a deeper look into her relationship with her son during an intimate chat while promoting “Carversations” on Instagram.
The popular photo-sharing app’s new video series highlights authentic conversations between parents and their teens, where some of the best conversations happen: in the car.
In the latest version of Instagram, Tom Brady talks with his son, Benny, about everything under the sun, including driving, the motivational quotes he sends him via direct messages (DMs), and the Brady family values that the Super Bowl champion instilled in his teenager’s head.
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Tom Brady talks with his son about how driving taught him to be independent
In the second episode of Instagram’s “Carversations,” Tom spoke with Benny about the independence driving gives him. According to Benny, driving is “definitely a refreshing feeling” that comes with some nice perks. “For the first time in my life, I can choose where I want to go and when I want to go,” Benny added.
The two men then joked about who pays for the car’s gas.
Although Benny eventually admitted that his NFL star father was footing the bill, it made him “feel more responsible and independent” when he said he did.
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What does Tom Brady send his son Benny via Instagram DMs?

Later in their conversation, Tom and Benny talked about the types of content they send each other in DMs.
While Tom sends Benny “motivational stuff”, Benny admitted that he sends “such stupid and funny videos”.
For Tom, however, sending motivational content to his son has a deeper meaning than he realizes in the moment.
“I think it’s fun to send you crazy stuff every once in a while,” Tom said. “But I think for the most part, if I’m going to share things with you, I want you to look at them and see real value in them. Like, ‘Why would Dad send me that?'”
As the conversation around DMs evolved, Benny imagined which megawatt celebrity he would message from Tom’s account if he had the chance.
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“Alright, so first of all, I want cool clothes. I’m going to direct message really cool companies, really cool people, maybe like Travis Scott, Drake, musicians that I like,” Benny said. “I’ll say ‘Hey, I need some clothes, I’m going to this thing. Make sure it’s a size smaller, though. I started losing muscle recently.'”
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What family values did Tom Brady instill in his son, Benny?
Tom and Benny spent part of their “Carversation” discussing more serious topics, including the values that matter most to their family. When Tom asked Benny to share some “Brady family values” that he carries with him wherever he goes, Benny brought up one that he said has become second nature.
“I mean, the biggest point that you literally drilled into my brain is that being cool is being caring. Like, cool people are people who care. And I mean, I literally hear it in my sleep the number of times you tell me that. It’s getting a little scary,” Benny said before sharing that he tries to live by that mantra every day.
“I feel like that’s the case. Like, you’re not going to be 100 percent perfect all the time, but what you can be is you can learn from your mistakes and you can grow from those mistakes,” Benny said.
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Why Benny Brady Thinks His Dad Has Reached ‘Unc’ Status
Tom, known for his time with the New England Patriots and Tampa Bay Buccaneers, also took a moment to speak with Benny about how the world has continued to evolve. To drive the point home, Tom mentioned how much football recruiting has changed since he attended the University of Michigan in 1995.
Tom told his son that back then he had to physically send a VHS tape to recruiters, whereas today everything is digital. “I think it’s a lot different now, like, you probably see a lot of stuff on Instagram. It was a totally different time where there wasn’t anything like these devices when I was a kid where you could share information,” Tom said, to which Benny replied, “Unc.”
But Benny didn’t stop there. He added a little more salt to the wound, jokingly calling his father “old.”
Tom Talks Shit During Netflix Roast
Tom has been extremely open about his relationship with his children, and during a previous podcast appearance, the elite athlete opened up about how his 2024 Netflix roast affected them.
“As a parent, there are certain things you screw up, and you don’t realize it until afterward,” Tom said, admitting he wasn’t a perfect parent. “You will see as you grow up that there is no perfect manual for this.”
Tom elaborated, revealing that the roast, which included jokes about his divorce from his ex-wife, Gisele Bündchen, hit too close to home for his children.
“…I will never forget when I spoke to my children the next day. It felt like a stake in my heart, understandably,” he said. “They protect their mother and father and everyone.”
