Bailey Anne Kennedy, who made history in June as the first transgender woman to win Miss Maryland USA, admits that her coronation hasn’t fully sunk in yet — she even says she’s slept next to her crown to make sure it wasn’t a fantasy.
But as she prepares to compete for the Miss USA title, Kennedy tells PEOPLE that her accomplishment wasn’t just a dream come true, but an important door that’s been opened for others.
“For the longest time, it wasn’t possible for someone like me to compete — let alone compete and win,” Kennedy, 32 says ahead of the Miss USA pageant, which will broadcast Sunday, Aug. 4 on the CW. “It’s not just a big deal for me. It’s a big deal for many communities that I represent.”
Her Miss Maryland USA title win on June 1 was notable for several reasons: in addition to becoming the first transgender woman to win, she also earned the distinction of being the first Asian American, first spouse of a military service member, and the first contestant over the age of 28 to earn the crown.
Even more impressive? It was the first pageant she participated in.
“I feel a tremendous honor,” Kennedy, who is from Montgomery County, says. “But at the same time, I feel an obligation to do a good job and contribute to society as much as I can in a positive way…It’s a responsibility, too.”
Kennedy recalls that after being named as one of the top 5 finalists during the pageant, she realized the potential of making LGBTQ+ history if crowned.
“I couldn’t stop crying,” she says, acknowledging that at the front of her mind were “all of those children who grew up not seeing someone that looks and sounds like them in this particular desirable position.” “
She adds, “I was one of them, 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.”
Another special moment came when she served as the grand marshal at a Pride parade. “One mom came up to me with her entire family, including her trans daughter, and she told me how much my representation means to them,” Kennedy says. “Imagine the thing I could do if given the honor of being Miss USA because I could shine the light on someone and give them hope that ‘Hey, there is actually a light at the end of the tunnel!’ ”
The current Miss Maryland USA lives by her motto of “beauty without an expiration date,” meaning that “you can start late [in life], look different, be uncertain and still somehow succeed.”
“If my life story can be a testament to that, I’ll be very happy,” she adds.
Kennedy’s drive can be traced back to her childhood when, at the age of 11, she and her family emigrated from Cambodia to Silver Spring, Md. — and growing up, she says she helped her parents sell pho, a Vietnamese soup dish, before and after school.
Being an immigrant child in a new country was a culture shock for Kennedy, but she saw that obstacle as a challenge.
“I will forever feel like [it] is my superpower,” she says, “because I came here not knowing English, not knowing the culture, but was able to adapt to it quickly and thrive in it – that’s important for people to know that immigrants can dive into the unknown and come out successful in the end.”
She initially considered becoming a doctor, even studying pre-pharmacy at the University of Maryland, Baltimore County. But, as she says, “life changes and goals change…it’s okay to adapt and find your calling.”
“Again, this is beauty without an expiration date,” she explains. “You’re never too old or too late to restart.”
Kennedy grew up an avid follower of beauty pageants — which in Asia are the equivalent to America’s Super Bowl, she says — and she always hoped she’d be able to compete and use her title to make a mark on the world.
“I know the title will open doors for so many philanthropic endeavors,” Kennedy says. “To see what they have been able to accomplish with their careers, I knew that I wanted to do that as well.”
About a year ago, the Miss Universe Organization allowed adult women of all ages to participate in its pageants. Previously, only women between the ages of 18 and 28 could enter.
Kennedy says she took inspiration from Judge Judith Sheindlin, better known as Judge Judy, when she entered the Miss Maryland USA pageant. “[Judge Judy said] if you didn’t make it in your 20s, you can still make it in your 30s,” says Kennedy.
Married to a member of the U.S. Marine Corps, Kennedy works as a volunteer representative for the United Service Organization (USO) supporting military spouses and their kids.
“It’s truly a passion because I’ve been advocating for military spouses and children of our military dependents at the USO office.” Kennedy adds. “I’ve been advocating for them to believe that the impossible is always possible.”
With her sights set on the crown, Kennedy says that no matter the outcome of this year’s Miss USA pageant, she still plans to continue her work with the USO.
“I’m going to be championing for children [and] military spouses,” she says. “I remember having to move out of my hometown and not having any kind of resources out there. To be that bridge between the pageant and using my voice and advocating for military spouses will make a tremendous difference in our community.”
The 73rd Miss USA Pageant will air live on The CW on Sunday, Aug. 4.
