

Linda Holliday may be best known to the public for her long-term relationship with NFL coaching legend Bill Belichick, but her personal and professional achievements reveal a much deeper story.
A graduate of Vanderbilt University with a degree in radiography, Holliday built a successful career in medical sales-specializing in X-ray machines, MRI and CT equipment, and breast imaging technology. Despite her extensive work in the healthcare industry, many people in Boston only recognized her for her television presence on Style Boston, where she began appearing in 2009.
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“There was surprise when I mentioned I spent 15 years in medical device sales,” she said, reflecting on how her identity had often been reduced to fashion and public appearances. That, however, couldn’t be further from the truth.
Holliday also took an active leadership role during her years with Belichick, serving as the president of the Bill Belichick Foundation. She emphasized that her involvement was not just symbolic-she and Belichick reviewed every application submitted for the foundation’s mentorship and grant programs.
Through this work, she connected with a wide range of philanthropists and advocates, including the late billionaire Leonard Lauder.
A tribute to Leonard Lauder’s legacy
On June 14, 2025, Leonard Lauder passed away at the age of 92. Known for transforming Estée Lauder Companies from a modest family brand into a global empire worth over $15 billion, Lauder also made his mark as a generous patron of the arts and healthcare.
He famously donated his $1 billion Cubist art collection to New York’s Metropolitan Museum and was the honorary chairman of the Breast Cancer Research Foundation.
In an emotional Instagram tribute, Holliday honored his passing. “Honoring Leonard Lauder’s incredible legacy today. His unwavering support for the Breast Cancer Research Foundation has touched countless lives. His dedication to advancing cancer research will continue to inspire us all. Thank you, Leonard, for your remarkable impact. Rest well,” she wrote, accompanied by a photo of them smiling together.
The message was especially meaningful given Holiday’s own background in breast cancer imaging and her continued commitment to advocacy in that space.
A new chapter with family
Now living in Nantucket, Holliday has shifted her focus toward family life. She’s the proud mother of twin daughters, Ashley and Katie Hess. Both attended Trinity College, with Katie majoring in American Studies and Ashley participating in the school’s a cappella group.
On her recent birthday, Ashley posted a heartfelt message calling her mom “the best of all time” and “the light in our big universe.” The post captured what many who know Holiday already believe-her biggest legacy isn’t her past partnerships, but the love and strength she brings to those around her.
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