bailey anne kennedy made history as the first transgender woman to win miss maryland usa — now, ahead of her quest to win the miss usa crown, here's. bailey anne kennedy was crowned miss maryland usa on june 1, making her the first trans woman — as well as the first asian american and military wife — to. when bailey anne won the 2024 miss maryland usa pageant in june, she shattered nearly every barrier in the book as the first trans asian american military wife. bailey anne kennedy became the first transgender woman and the first asian american to win the title of miss maryland usa on june 1. Married to a member of.
