New York – While the spotlight has often shone on 73-year-old NFL icon Bill Belichick, his 24-year-old girlfriend Jordon Hudson has been quietly building a business empire of her own—one property at a time. Recent reports reveal that Hudson, a former cheerleader and pageant queen, has amassed an $8 million real estate portfolio in under a year, with multiple property purchases in the Boston area and beyond.
A Real Estate Spree Behind the Scenes
According to Realtor.com, Hudson began acquiring properties in mid-2023, just months after she was first publicly linked to Belichick. Her real estate shopping spree includes four homes bought in a matter of months—three of which are multi-family dwellings designed to generate passive rental income. The acquisitions were largely made through limited liability companies (LLCs), with Hudson listed as the borrower on each mortgage, underscoring her direct involvement.
Strategic Property Investments
Hudson’s real estate venture began in June 2023, when she purchased her first property in Dorchester, Massachusetts, for $2.3 million. According to property records, she took out a $1.2 million mortgage in December 2023. On the same day, she reportedly secured another $1.2 million mortgage for a second townhouse in the same neighborhood, this time priced at $2.2 million. The second home, already converted into three apartments, was promptly updated with modern features and is currently being rented for $5,000 a month.
She also divided the first townhouse into separate apartments, maximizing rental revenue.
In October 2023, Hudson acquired a two-bedroom cottage in Harwich, Massachusetts, for $610,000—a charming single-family home that added to her growing portfolio.
Her most significant acquisition came on December 15, 2023, when she purchased a $3 million multi-family property in Boston’s Roxbury Crossing. The massive building features 15 bedrooms and 8.5 bathrooms spread across three units, and it was already generating $17,675 in monthly rent at the time of purchase, with leases locked in through August 2024.
18 Companies and Counting
Public records also suggest that Hudson has established at least 18 companies under her name, most registered in Massachusetts. These LLCs were likely formed to manage various property acquisitions and streamline operations—an advanced strategy often used by experienced real estate investors. Each property she purchased appears tied to a unique LLC, signaling a deliberate and well-organized expansion plan.
A Timeline That Raises Eyebrows
Hudson’s rapid rise as a property investor coincided with a turbulent time in Belichick’s career. The longtime New England Patriots coach parted ways with the franchise in January 2024. However, he quickly rebounded by signing a five-year, $50 million contract with the University of North Carolina, ensuring his return to the sidelines.
Hudson’s public visibility has also increased during this period, sparking engagement rumors after she was seen wearing a ring on her left hand. She even made headlines by stepping into a CBS interview with Belichick to shut down probing questions about their relationship—prompting jokes from Dave Portnoy and criticism from Megyn Kelly, who speculated on the age-gap dynamics and raised concerns over “elder abuse”.
Belichick later defended Hudson, saying they share a “personal and professional relationship”, and that her remarks reflected his own thoughts on media intrusion.
From Cheerleader to Real Estate Mogul
What began as a low-key romance between the legendary NFL coach and a college student has turned into a lucrative business journey for Jordon Hudson. While some continue to question the relationship’s dynamics, her growing real estate empire suggests that Hudson is focused on more than the headlines—she’s building long-term wealth with strategy and speed.
