Bailey anne kennedy was crowned the new miss maryland usa in june, the first transgender woman and the first asian american to win the title. 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 everything you need to know about the. A trans woman has won miss maryland usa and made history in the process with a list of pageant firsts Bailey anne kennedy was crowned on saturday, breaking nearly every barrier that existed in the state pageant's history.
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