Bill Belichick, 72, Is Roasted Over 48-Year Age Gap With His Girlfriend, Jordon Hudson, 24—but His Property Portfolio Is No Laughing Matter

Former New England Patriots coach Bill Belichick, 72, and his 24-year-old girlfriend, Jordon Hudson, became the surprise stars of the NFL Honors when they were mercilessly roasted by rapper Snoop Dogg over their 48-year age gap.

Belichick, who led the Patriots to six Super Bowl wins, has been dating Hudson since early 2023, less than a year before he announced he would be stepping down as New England’s head coach.

However, at the 2025 NFL Honors ceremony on Feb. 6, it became clear that the romance still hasn’t lost its comedic appeal—with Snoop holding nothing back as he skewered the duo over their unconventional coupling.

Telling the crowd, which include the likes of 2025 MVP Josh Allen and fiancée Hailee Steinfeld, that he’s been “a football fan for a long time,” Snoop, 53, said that many things have changed since he first started watching games “back when the Cowboys was good” and “when the Chiefs was bad.”

“And I remember, what was it—Bill Belichick’s girlfriend wasn’t even born yet?” he joked, leaving Hudson open-mouthed in surprise, while her partner simply chuckled along with the rest of the audience members.

It is far from the first time that Belichick and Hudson’s romance has been the butt of a joke. In fact, the longtime coach’s dating life wasn’t even spared by two of his most successful players, Tom Brady and Rob Gronkowski, both of whom savaged him over it during Netflix’s “The Roast of Tom Brady.”

“Coach, you used to talk about Foxborough High School when we sucked,” Gronkowski said during the livestreamed special on May 5, 2024. “But now I know why you were so obsessed with Foxborough High School: You were scouting your new girlfriend.”

Brady then followed that up by mocking Belichick over Ring camera footage that caught him sneaking out of Hudson’s home shirtless, saying: “Everybody asks me which ring is my favorite, I used to say ‘the next one.’

“But now that I am retired, my favorite Ring is the camera that caught Coach Belichick slinking out of that poor girl’s house a few months ago. Hey, you still got it. Respect baby.”

The home in question was located in Massachusetts home where former cheerleader Hudson was living at the time—having attended Bridgewater State University.

What remains unclear is whether Hudson is still living in her own abode, or if she has moved in with Belichick into one of his many abodes.

Because, despite jokes being made at their expense, the couple have proven themselves to be serious about one another—even fueling engagement rumors after Hudson was seen wearing a large sparkler on that finger.

Like Hudson, who proudly states on her Instagram account that she is the “daughter of Maine fishermen,” Belichick has long called Massachusetts home—or homes, if you count the multitude of properties that he has owned in the state over the years.

Despite taking up a new position as the head football coach at the University of North Carolina, Belichick shows no signs of wanting to part ways with his expansive property portfolio—although he may well opt to snap up a home in Chapel Hill should his new gig go well.

And when the going gets tough and the season takes a downturn, the duo can always escape to his palatial condo in Florida.

Inside Bill Belichick’s Massachusetts mansions

In 2006, Belichick—whose net worth is over $70 million—reportedly snapped up his first Massachusetts home for a relatively modest $1.4 million.

The three-bedroom, three-bathroom home sprawls across 4,400 square feet and boasts a two-car garage.

According to the original listing, the property overlooks a third hole on a golf course and features two pools, a tennis court, a clubhouse, and a recreation center.

Inside, there is a media room, wine cellar and wet bar.

Although he purchased the charming abode for $1.4 million, Realtor.com^® now estimates Belichick’s property is worth $2.1 million.

In 2024, he forked over $4.8 million for a Nantucket property that offers 2,854 square feet of living space.

The four-bedroom, four-bathroom property was built in 1983 and boasts an expansive living area, a sophisticated dining space and an office space.

On the second floor, there is an en suite primary bedroom and two guest rooms with a shared bath.

The property was renovated in 2017 and features a basement with an additional bathroom and tub.

Belichick previously gushed about Nantucket while speaking to N Magazine in 2017, telling the outlet: “The island is spectacular. The people are great, fishing, bike paths, the lighthouses, the beach, the history—I mean it’s got it all.”

The legendary coach once held the keys to another Nantucket property, which he purchased for $4.6 million in 2006; however, property records indicate that the home went to his ex-wife, Debby Clarke, after they divorced that same year.

According to the documents, the former couple purchased the home together, however, it is now solely registered in her name.

The property boasts five bedrooms, four bathrooms, and several cozy fireplaces.

Florida condo

When isn’t enjoying one of his many homes in Massachusetts, the NFL coach is laying low in his stunning Florida condo, which he purchased in 2009.

The four-bedroom, three-bathroom home sprawls across 4,085 square feet and boasts 20-foot ceilings and sweeping views of the deep sea.

Although he snapped up the property for $1.6 million, Realtor.com now estimates it is worth $3.7 million.

The property is located right off of a golf course and boasts a wine cellar and an encircled patio.