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A graduate of Stuyvesant High School in New York, Kolakowski was the first person in her family to graduate from college. She received a Bachelor of Arts in Natural Sciences from New College of Florida in Sarasota, FL; then went onto receive a Master of Sciences in Biomedical Engineering from Tulane University and a Master of Sciences in Electrical Engineering from the University of New Orleans, LA. She received a joint Juris Doctor (law) degree and Master of Public Administration (with an emphasis on budget and finance) from Louisiana State University in Baton Rouge, LA.
After graduating from Louisiana State University law school, the Louisiana State Bar Association cited Kolakowski's gender transformation as reason for prohibiting her from taking the bar exam. The Louisiana Supreme Court sided with Kolakowski, when she appealed the decision allowing her to take the bar exam.
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Kolakowski began her transitioned from male to female in the 1980s and underwent gender reassignment surgery in 1991.
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She also quickly got involved in community and professional leadership activities throughout the Bay Area. She serves on the Oakland Budget Advisory Committee and is co-chair of the board of directors of the Transgender Law Center, a non-profit organization dedicated to eliminating discrimination against the transgender community.
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She also went on to earned another degree, this time a Master's of Divinity from Berkeley's Pacific School of Religion and served as a chaplain at the University of California San Francisco Medical Center. She is an ordained minister in the Universal Fellowship of Metropolitan Community Churches.
She serves on the California Council of Churches and is a volunteer clergy member at the New Spirit Community Church.
In 1994, the East Bay Lesbian/Gay Democratic Club named her Woman of the Year. In 1995, she received the Outstanding Woman of Berkeley Award.
In 2010, having served as a lawyer for twenty one years, and an administrative law judge for four, Kolakowski campaigned for a judgeship on the Superior Court of Alameda County, California. She won by 10,000 votes with 51% of the vote to her opponent's 48% on November 2, 2010.
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She was sworn in this past January.
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They live in Oakland with their Pembroke Welsh Corgi Nicky (CH Faerie Glen Snickerdoodle) and cats Puff and Espresso.
"Throughout my career, once my colleagues found out that I am transgender, there was always a curiosity for a day or two and then I just became Vicky."
"I have been very fortunate to have a successful career as a public servant, and I feel an obligation to serve my community as a role model as well.”