When Bill Belichick dressed up as a pirate after Randy Moss' Halloween party invite: "You might win the damn prize"

Former New England Patriots coach Bill Belichick may have won numerous Super Bowl and AFC titles with his dynasty team, but it’s still hard to spot him with a smile. Known for maintaining a serious demeanor throughout his coaching career, Belichick surprised everyone in 2009 when he was invited to a Halloween party by former Patriots wideout Randy Moss.

The NFL shared a video on its official YouTube channel in October 2015 and 2022 as a throwback to the epic moment when Belichick dressed up as a pirate, shocking everyone. However, it all started with a simple invitation from Moss, who approached Belichick in his office.

Moss said, “We’re trying to… from a team standpoint, we’re trying to have a Halloween party. So you’re not interested in that? Are you?”

Belichick responded, “We come dressed as a devil?”

Moss replied, “This is what it is… Well, you might win the d**n prize. You know, get us a little DJ, get us a roller rink and you know… have us a good night. Like I said, you’re more than welcome or whatnot.”

Belichick eventually showed up in a black leather outfit, dressed up as a pirate and looked like Captain Jack Sparrow, played by Johnny Depp, from the Pirates of the Caribbean franchise. Belichick cosplayed his role with perfection as he wore a black hat, an eye patch, and carried a plastic sword to complete the look.

He was accompanied by his then-girlfriend, Linda Holliday, who dressed up as one of the pirate girls. Holliday even posed with Belichick as the coach seemingly held her hostage by placing the sword on her throat. She shared the photos on her Instagram.

Belichick and Holliday split up in 2023 after being together for 16 years. The post has since been removed from her profile.

Randy Moss and other New England Patriots enjoy Halloween with Bill Belichick

Meanwhile, the party was attended by other Patriots players, including Aqib Talib, Brandon Spikes and LeGarrette Blount, as they too got into the holiday spirit. They dressed up as the SWAT guy, Chuckie and a pirate, respectively.

Moss dressed up as SpongeBob SquarePants while DT Vince Wilfork went as Fred Flintstone as the Patriots enjoyed their bye week. They all looked stunned to see their coach making his entrance in a Halloween costume.