Truths About Linda Holliday’s Relationship With Bill Belichick, Her Divorce and Daughters

Linda Holliday is an American model, former beauty pageant contestant, fashion aficionado, businesswoman, and ex-lifestyle reporter. However, she is more popularly known as the longtime girlfriend of one of the most successful coaches in the National Football League (NFL).

Since she started dating her current boyfriend, she has been a pillar of support to him, cheering him and his team to many championship trophies and awards. They have become one of the most admired couples in the NFL, with Linda renowned for showing the gentle side of the coach’s intimidating persona since their affair began in 2007.

A Fateful Meeting in a Florida Night Club Started Linda and Belichick’s Relationship

Entering 2007, Bill Belichick was a single man. He had completed his divorce with his wife of 29 years, Debby Clarke Belichick, in 2006. At the same time, Linda Holliday, a former beauty pageant contestant and lifestyle reporter, recently ended her marriage to her third husband.

Both were in the dating market. Well, sort of. Linda was seeing someone at the time her world collided with the NFL legend’s in 2007. They met in a nightclub in 2007 while Linda was on a girls’ night out with her friends in Palm Beach, Florida.

One thing led to another at the club, and 13 years later, they are still going strong. Other than the fact Linda ended her evolving relationship at the time to date the Patriot’s coach, the exact circumstances that cemented their relationship remained undisclosed.

However, since the world came to accept them as a couple, Linda Holliday has been one of the regular fixtures of Bill Belichick’s life, other than football. Linda has been the conduit through which fans of the NFL learn about the other side of the iconic coach.

When she is not posting photos of them before and after matches, she is publishing pictures from their vacations worldwide. The couple particularly holidays at Nantucket, Massachusetts. The media content posted by Linda on each visit offers insight into the gentle and loving side of Bill when he is not marshaling tens of men to the Super Bowl.

The Duo Might be Engaged

Having dated for more than a decade, it would not be out of line to wonder if Linda Holliday and the NFL coach will walk the aisle. And while it appears both parties are comfortable with their current arrangement, there is evidence to suggest they are considering moving things up a notch.

In a picture posted on December 22, 2019, Linda can be seen wearing a custom-made sparkly Patriots jacket. Paired with the jacket is what appears to be a massive diamond ring on her left hand. There has been zero confirmation from either party, particularly Linda, on an engagement, which is strange considering how celebratory she is when it comes to the couple.

The popular theory about the fact is Linda might have been keeping it a secret to allow the Patriots and Bill get through the 2019 playoffs. But as of August 2020, months after their season ended, there is still no confirmation from the couple. For now, the speculation lingers, and the couple continues to nurture their long-running relationship as they see fit.

No Children but They Run a Foundation Together

Linda Holliday
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They might not be married, and their relationship may not have produced children. Still, Linda Holliday and Bill Belichick have a baby of their own. They are owners and caretakers of the Bill Belichick Foundation, which caters to individuals, communities, and organizations that need athletic support.

Founded in the early 2000s, Linda Holliday serves as Executive Director of the organization. Before taking up the role, she worked in TV as a lifestyle correspondent for Style Boston and ran a boutique. Under her, BBF focuses on football and lacrosse and has donated several thousand dollars to various individuals and organizations as part of its mission to build the athletic leaders of tomorrow.

Aside from their work on the organization, Linda and Bill also support other foundations and charities. They are particularly known for supporting charities working to raise breast cancer awareness.

Before Belichick, Linda Holliday had been Married Thrice

The world knows that Bill Belichick used to be married to Debby Clarke Belichick, his high school sweetheart, from 1977 to 2006. Their 29 years marriage ended officially in 2006, after two years of separation following alleged infidelity by the Patriots coach.

The marriage produced three children, two sons, Stephen, and Brian, who now work in the Patriots organization. He also has a daughter, Amanda, who is the head coach of the Holy Cross College women’s lacrosse team. Unfortunately, the same depth of information cannot be said of Linda’s romantic past.

So far, all we know is she had been married thrice, to men whose identities remain a mystery. Online reports suggest the men are Vaughn Corder, Eugene Holliday, and Dennis Hess. Her alleged marriage to the latter produced twin daughters, Katie and Ashley Hess.

Her Daughters, Katie and Ashley, are Social Media Influencers

Sometime in 1992, Linda gave birth to twin daughters named Katie and Ashley Hess. According to an in-depth article about the twins, their father, whose exact identity remains speculation, is an avid hobby photographer based in Georgia. Katie, who is older, came into the world 7 minutes earlier than Ashley. Linda Holliday did not disclose if she was ever married to their father, nor has she ever shared information about him. The twins are young women now, and just like their mother, they live an exciting life and lifestyle.

The twins graduated from Trinity College in Connecticut in 2015. They were writers and reporters for the college magazine with a focus on beauty tips, in vogue styles, health and wellbeing, and a host of other subjects. The twins were also members of an acapella group in college called “The Dischords”; Katie was the group’s Soprano and sometimes Alto, while Ashley sang Alto and Tenor.

Katie and Ashley spent a semester of college in France, studying. France is a city of romance and fashion, and the girls took note of this while studying in France. They decided to write about their fashion experience in France once they returned to the United States. This passion would eventually give birth to the fashion and lifestyle blog, TheHessTwins.

They also have an Instagram presence, where they have over 25,000 followers and have become fashion influencers. Katie and Ashley took up influencing full time after college in August 2015 and have recorded a few notable successes. They have deals with Equinox, Jugos, AllSaints, Concepts. They have also been featured in major publications like the Huffington Post and Boston Magazine.

The Hess Twins are DJs too

Aside from fashion influencing, Linda Holliday’s twin daughters are also DJs. Their DJ style is self-described as universal and open format, covering different genres and ages of music. So far, it has helped the twins secure gigs with international and local brands. They have worked with Converse, Tiffany & Co., Nike, Vibram, and Bulgari.


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