Monson Man to Square Off Against Bill Belichick’s Squeeze in Miss Maine USA Beauty Pageant

by Steve Robinson | Apr 16, 2025

When the head-turning girlfriend of former New England Patriots head coach Bill Belichick takes the stage in this year’s Miss Maine USA beauty pageant, she’ll be squaring off against another eyebrow-raiser: Isabelle St. Cyr, a 24-year-old Monson man who now identifies as a woman.

According to a report in the Bangor Daily News, St. Cyr is set to compete in the beauty pageant, which crowns Maine’s representative for the national Miss USA contest. The event, a glitzy affair featuring a swimsuit strut, evening gown parade, and a high-stakes interview, has no rule requiring that entrants be women.

Per the BDN, St. Cyr will become the first ever biological male to participate in the beauty pageant, which dates back as far as the 1950’s.

Belichick’s 24-year-old girlfriend, Jordon Hudson, who finished as the first runner-up in last year’s contest, posted on Instagram on Tuesday that she, too, will toss her hat in the ring. But the Hancock native might find herself serving as second banana to St. Cyr thanks to Maine’s ongoing position in the middle of the national debate over transgenderism.

The fight over trans ideology escalated on Friday when Maine Attorney General Aaron Frey (D) sent a letter to the Trump Administration informing U.S. Department of Education that Maine’s state government will not voluntarily comply with Title IX rules that require entities receiving federal funding to keep male and female athletics separate.

Currently, Maine’s high school sports policies force female athletes to compete against male athletes who identify as female.

Pageant judges looking to strike a blow against President Donald Trump (R) might just put their thumbs on the scale in favor of St. Cyr, regardless of what the Supreme Court has said about affirmative action.

According to the pageant website, the only requirements for entry into the contest, which will determine who represents Maine in the national Miss USA pageant, are to be a U.S. citizen, a resident or full-time college student, and a “medically recognized” female.

Steve Robinson is the Editor-in-Chief of The Maine Wire. ‪He can be reached by email at [email protected].

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