Former New England Patriots coach Bill Belichick’s relationship with 24-year-old Jordon Hudson has been at the forefront of some jokes recently. Belichick is currently 72 years old, and their age gap is a target for comedic relief.
Tom Brady interviewed with former Barstool Sports’ Caleb Pressley, and Pressley poked fun at Hudson’s age compared to Belichick.
Tom Brady’s Reaction to the Joke
Brady couldn’t help himself when Pressley made a joke about Hudson renting a car.
Pressley asked, “If Bill Belichick’s girlfriend needed it, would you rent a car for her?”
Watch Tom Brady hilariously react to joke about Bill Belichick's girlfriend pic.twitter.com/jqGPaGVAGb
— New York Post (@nypost) February 11, 2025
Pressley’s stone-cold delivery had Brady dying laughing. Brady tried to hold in his laughter but he simply couldn’t.
Belichick’s Relationship and Age Gap
Belichick and Hudson made first contact with each other on a flight to Florida. They conversed over a book, exchanged contacts, and Belichick gave Hudson an autograph. They stayed in touch and eventually began dating privately in 2023.
Belichick’s had two long-term relationships. He was married to Debby Clark for almost 30 years and had three kids together, but they reportedly divorced in 2006. Also, he reportedly jumped into a relationship with Linda Holliday in 2006 that lasted until 2023.
Soon after, he started dating Hudson. They are 48 years apart and kept their relationship flying under the radar. According to TMZ, Hudson attended Patriots games in secret until their relationship went public at Brady’s New England Patriots Hall of Fame induction ceremony in June 2024. They posed for photos together on the red carpet, officially launching their relationship to the public.
Hudson played an important role in Belichick’s life in his one year out of coaching, helping him with broadcasting deals. Now, he is the head football coach at the University of North Carolina. The jokes write themselves as Hudson is similar in age to the players that Belichick will be coaching.
Pressley wasn’t the only person to make a joke about Belichick’s relationship recently. At the NFL Honors ceremony, Snoop Dogg hosted and brought up his history as an NFL fan. His support of the NFL goes back to the days when the Dallas Cowboys were good and the Kansas City Chiefs were bad. Snoop Dogg followed that up by asking the crowd if Hudson was even born yet and was rewarded with some laughs.
The jokes don’t stop there, though. In the Roast of Tom Brady on Netflix, Rob Gronkowski made sure to make the most of this opportunity to troll his former coach.
“You used to talk about Foxborough High School when we sucked, but now I know why you were so obsessed with Foxborough High School: You were scouting your new girlfriend!” said Gronkowski.
Belichick and Hudson’s relationship isn’t safe from anyone. The age gap leaves a giant target on their backs for people to crack jokes. Even Belichick’s trusted former players are getting in on the trolling.
Yet, Belichick and Hudson keep on going, even with all the outside noise and jokes.