At 73, Bill Belichick, one of the most successful coaches in NFL history, is once again in the spotlight—this time, not for football, but for his personal life. According to multiple reports, Belichick is now engaged to Jordon Hudson, a 24-year-old former college cheerleader, sparking widespread debate due to the 49-year age difference between them.

The romance between the former New England Patriots coach and Hudson began making headlines in 2023. Although the relationship was kept under wraps at first, it became public in mid-2024 when the couple made their red carpet debut. Since then, media attention has only intensified.

According to TMZ Sports, the couple first met on a flight in 2021, sitting next to each other on a trip from Boston to Florida. At the time, Hudson was 19 years old and studying logic, a subject Belichick showed interest in by signing the front page of her textbook. From that moment, a quiet but solid relationship began to form—one that would become official years later.

Bill Belichick reportedly engaged to a girlfriend who keeps stirring controversy

Recently, rumors of an engagement began circulating after Hudson was seen wearing a diamond ring on her left hand. While some sources claimed it was just a gift, The New York Times reported that Hudson had told at least one person they were, in fact, engaged.

What reignited the controversy was a viral interview in April 2025. During an appearance on CBS Sunday Morning, journalist Tony Dokoupil asked the couple how they met. Hudson immediately shut the question down: “We’re not talking about this.” Her reaction sparked a wave of criticism and speculation online.

Belichick later released a statement through the University of North Carolina, where he now coaches at the college level, clarifying that he had previously asked that interviews focus solely on his book The Art of Winning. According to him, the journalist ignored this agreement, and Hudson intervened to protect the integrity of the conversation.

Hudson, for her part, has responded directly to critics on social media. In one case, she publicly called out a user who messaged her to say the relationship was "insane." Her reply: “But you do realize direct messaging a stranger on Instagram with the intent of harassing them regarding their own personal relationship is insane, right?”

Before dating Hudson, Belichick was in a long-term relationship with Linda Holliday, who was a constant presence in his life and professional career. They separated in 2023 after 16 years together.

Now, Belichick and Hudson continue their relationship amid both support and criticism. With no official wedding date confirmed, one thing is clear: the story of this unlikely couple continues to fascinate and divide the public.