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Bill Belichick's romantic past collided headfirst with his present during a holiday party last December, turning an otherwise cheerful Nantucket event into a social standoff. The drama unfolded at Dreamland's annual "Stroll Party" on December 6-a celebration promoted as a community holiday bash on the island.
Hosted by Dreamland, a cultural nonprofit organization known for films and performing arts, the event was headlined by none other than Linda Holliday's daughters, Ashley and Kat Hess, popularly known as the Hess Twins, who DJ'd the night.
What started as a night of music and celebration quickly took a turn when Linda Holliday, Bill Belichick's longtime former partner, took issue with the unexpected appearance of Belichick's new girlfriend, 24-year-old Jordon Hudson.
Dance floor dispute draws attention at Nantucket gala
According to an incident report filed by a Dreamland official and obtained by TMZ Sports, Holliday believed Hudson's presence was inappropriate considering the family connection to the party.
"She asked that I remove Ms. Hudson from the premises," the official stated in the report.
Security footage later showed Holliday, accompanied by a few friends, confronting Hudson on the crowded dance floor where over 200 guests were gathered. The report details how the Dreamland staffer approached the women shortly after and watched Holliday and her group "back away."
When questioned, Hudson reportedly maintained her innocence and right to attend the event.
"I asked Ms. Hudson if she thought it was a good idea to be there considering the clear animosity the above individuals felt towards her," the official wrote.
"She defended herself by saying she'd done nothing wrong, and it was her first time attending Christmas Stroll and wanted to attend the 'big party' going on that night, which happened to be the one featuring the Hess Twins.
"She said she was not looking to cause any problems, but just wanted to go out and have fun with her friend."
While Hudson eventually agreed to leave-just minutes before the party was set to wrap up-she claimed Holliday had taken things further by allegedly intimidating Sapini during their earlier confrontation. Hudson told the Dreamland staffer that Holliday warned Sapini.
"If she valued her current title, she should think twice about who her friends are," and added she "had many powerful friends in the pageant organization."