Bailey Anne Kennedy, 32, has already made history this summer as the first transgender woman to win Miss Maryland USA.

Bailey Anne Kennedy, a Cambodian-American model and beauty pageant titleholder, was crowned Miss Maryland USA 2024. This victory marks several firsts: she is the first transgender woman, the first Asian American, and the first woman over the traditional age of 28 to win the title.

She represented Maryland at the Miss USA 2024 pageant in Los Angeles on August 4, 2024, becoming the second transgender delegate in the history of the competition, following Kataluna Enriquez of Nevada.

Kennedy's journey began in Cambodia, where she was born before emigrating to the United States at the age of eleven. Growing up in Silver Spring, Maryland, she was captivated by beauty pageants from a young age, often dreaming of the day she might compete. “I used to pray about it, and I didn't think it would come true to fruition,” Kennedy recalls. “Now that it’s happening,

it feels surreal. It hadn't truly sunk in at that time. At times, I have to sleep next to my crown just to make sure that it's happening.”

In 2024, Kennedy entered her first pageant and won the title of Miss Maryland USA. This victory was groundbreaking not only because of her transgender identity but also because she was the first Asian American, the first immigrant, the first military spouse, and the first woman over 28 to win the title.

Kennedy is married to Casey Gup, an officer in the United States Marine Corps. She also serves as a center representative for the United Service Organizations (USO), demonstrating her commitment to supporting military families.

Her life and career are testaments to her mantra, “Beauty Without an Expiration Date.” After the Miss Universe Organization changed its rules to allow women over 28 to compete, Kennedy's win at 31 became a powerful example of this belief. “No matter how old you are,” she says, “you can start late in life, look different, be uncertain and still somehow succeed.”

Kennedy's historic win is especially significant for the LGBTQ+ community. When she made the top five in the Miss Maryland USA pageant, she realized the enormity of potentially winning the crown. “I couldn’t stop crying,” she recalls, “because I remember how special it is for the LGBTQIA+ community – especially all of those children who grew up not seeing someone that looks and sounds like them – in this particular desirable position."

Kennedy is deeply aware of her role as a trailblazer. “I was one of them,” she says, “and this is why I always strive to make a good contribution to society because I want to make it easier for those who come after me.”

Bailey Anne Kennedy's journey from Cambodia to the Miss Maryland USA crown is a story of perseverance, breaking barriers, and inspiring future generations. Her achievements highlight the importance of diversity and representation, and her advocacy continues to pave the way for a more inclusive society.