A Life of Forking Paths: Judge Victoria Kolakowski’s (‘78) Journey As a Transgender Woman and Equal Rights Pioneer

Judge Victoria Kolakowski’s (‘78) Journey As a Transgender Woman and Equal Rights Pioneer

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By Grace Louie

Name: Victoria Kolakowski

Age: 62

Date of Birth: August 1961

Stuyvesant Graduation Year: 1978

Occupation: Judge


  • Bachelor of Arts in Natural Sciences from New College of Florida (1982)
  • Master of Science in Biomedical Engineering from Tulane University (1987)
  • Master of Public Administration from Louisiana State University (1989)
  • Juris Doctor from Louisiana State University (1989)
  • Master of Science in Electrical Engineering from University of New Orleans (1990)
  • Master of Divinity from Pacific School of Religion (1997)

Bio: Victoria Kolakowski (‘78), the first openly transgender trial court judge, has had many twists and turns throughout her career. Kolakowski studied biomedical engineering, law, public administration, electrical engineering, and divinity throughout her education. She came out as transgender during her final semester of law school, and had to petition the state supreme court in order to take the bar exam; she was originally denied this right due to her gender identity. Ultimately, Kolakowski became a successful judge as well as an advocate and educator of LGBTQ+ rights. Later, during her career as a minister, Kolakowski wrote three articles that formed a large basis for transgender scholarship surrounding the Bible. 

When Victoria Kolakowski (‘78) began her high school career, she could hardly anticipate the drastic transformations that would occur in the following decades of her life. From struggles with gender dysphoria to abrupt changes in her career to becoming one of the most praised figures in the legal fight for LGBTQ+ rights, Kolakowski has done it all—and done it well.

Born to a pair of high school sweethearts in Greenpoint, Brooklyn, Kolakowski’s early childhood was characterized by the hustle and bustle of a large family. “It was a three-story apartment building and [my grandparents] lived upstairs and we rented out the first floor,” Kolakowski said. “My dad’s whole side of the family was in and out [of the house] constantly.” Kolakowski’s father worked in a cardboard factory and her mother was a payroll clerk. 

Kolakowski completed junior high school in only two years, and was one of the youngest students in her grade when she began Stuyvesant; she graduated at just 16 years old. “All my friends played chess, did the math team, you know, normal teenage stuff,” Kolakowski joked. For her part, Kolakowski participated in a variety of unconventional activities; she was a member of the Rapid Transit Club, an editor for Studio (the now defunct Stuyvesant fine arts and mechanical drawing magazine), and ran for many student government elections. One of Kolakowski’s most exciting memories from high school was interviewing the esteemed science-fiction writer Isaac Asimov for a school project. She had the opportunity to visit his home and still has his landline number to this day. 

Along with the fulfillment these hobbies brought her, Kolakowski also fixated on an aspect of Stuyvesant that many students continue to prioritize today: her grade point average. “I could tell you [during my senior year] how much of an impact missing a question on an exam would have on my long-term GPA,” Kolakowski admitted. 

Kolakowsi was accepted to all the colleges she applied to—including the Massachusetts Institute of Technology—but the steep tuition costs prevented her from attending. Seeking a change in environment at a more feasible price tag, Kolakowski chose a college with a less GPA-oriented philosophy than Stuyvesant. “I went to a college that didn’t do grades: New College of Florida in Sarasota.” 

While Kolakowski enjoyed many aspects of Stuyvesant, those happy memories were often overshadowed by her prolonged struggle with gender dysphoria, a source of extreme distress impacting her since childhood. She endured incidents of transphobia throughout her youth, such as being called the F-slur for kissing a boy, an act that Kolakowski thought would make her more of a girl. When she attempted to find information regarding her gender identity in the New York Public Library, Kolakowski was alarmed to discover that magazines containing transgender figures had their pages ripped out, and all other transgender content was kept in locked-up sections of the library. 

In one of her most disquieting memories from Stuyvesant, Kolakowski recalled an incident in her English class regarding an assignment from her teacher Frank McCourt, Pulitzer Prize-winning author of the memoir Angela’s Ashes (1996). “He gave me a writing assignment that absolutely destroyed me. I was supposed to write a scene for a play in which a young man comes out to his father as gay.” Terrified that her peers would find out the truth about her identity, Kolakowski handled the situation in the only way she knew how. “I wrote something so awful that it would prove that I could in no way identify with a character with a shameful secret. It was full of wooden dialogue between stereotypical characters, who secretly were surrogates for my worst fears about what would happen if I told my father about my secret,” Kolakowski admitted. “It earned me my worst grade in high school. [...] It was my greatest shame.” To this day, Kolakowski still internalizes McCourt’s harsh critique of her piece. “That day, Mr. McCourt’s scathing statements that I had written unrealistic dialogue were burned into my mind. [...] He expressed his deep disappointment in me, in my abilities, and in my attitude towards this simple task.”

It was not until college that Kolakowski finally had the resources to explore her gender identity. “When I went off to college, I was finally able to get information about being trans. [...] I was using therapists and all this stuff. And when I graduated, [I went] to New Orleans, and was seeing a gender specialist there,” Kolakowski recounted. However, developments with her sexuality confused her: “I was just getting ready to transition when I fell in love with a woman, which very much confused me because I didn’t know that you could be a woman and be in love with one,” Kolakowski said. That relationship eventually ended, and Kolakowski’s struggles with her gender identity continued to impact her ability to find love. “My gender identity [...] dramatically reduced the dating pool. Most people were unwilling to date me because of this, and though I am bi[sexual], no guy has shown any interest since I was an undergraduate.” However, she eventually found love with journalist Cynthia Laird, and they were happily married in 2008. After attempting to live as a man for a few more years, Kolakowski eventually revisited her plan to transition, beginning the process in her last semester of law school.

           Before pursuing law, Kolakowski began college as a biomedical engineering major out of a desire to help people. Originally interested in rehabilitative biomedical engineering, Kolakowski ended up focusing on biomaterials. However, she struggled to find a job after graduation. “Nobody knew what it was that I did,” Kolakowski said. “I talked to a woman who had been in a similar situation two or three years earlier, and she said ‘I went and got an electrical engineering degree and everyone wanted [to hire] me.’” Inspired by her peer’s success, Kolakowski studied electrical engineering at the University of New Orleans after law school. Kolakowski also pursued a doctorate in physics, but dropped out because she had a love-hate relationship with the subject. “I could have been an adequate physicist, but I didn’t want to be an adequate anything,” Kolakowski said; she preferred to be exceptional at all that she did. 

           While she excelled in a variety of engineering fields, Kolakowski found herself longing to make a difference for people struggling with the same discrimination and dysphoria that she faced. She chose to pursue a joint juris doctor (J.D.) and master of public administration degree for this exact purpose. “I did a lot of work on behalf of the LGBTQ+ community in the 1990s, which was the first decade of my career,” Kolakowski said. “I was either chair or co-chair of the Bay Area Transgender Law Association. [...] I worked on statewide legislation, local legislation, education for the legal community, and more. I co-represented a trans man who was pulled out of a single-stall men's room in front of the Berkeley Police Review Commission. In 1999, I was one of the founding officers of the statewide organization California Alliance for Pride and Equality (CAPE), which was later renamed to Equality California. [...] Later, I served as co-chair of the board of the Transgender Law Center in San Francisco.”

            Kolakowski fully transitioned in her final year of law school and felt genuinely comfortable in her own skin for the first time. However, she experienced greater discrimination after transitioning, especially as she began her career. “[People around me] didn’t handle it very well,” Kolakowski said. Upon showing up to law school one Monday morning in a dress, Kolakowski’s world turned upside down. Her peers shunned her and she was denied access to all bathrooms on campus except the chancellor’s singular restroom. Kolakowski had to jump through several legal hoops in order to gain the necessary paperwork to graduate, and when she applied to take the Bar exam, the agency denied her application on the grounds that she was not of “sane mind.” After petitioning the Louisiana Supreme Court to take the Bar, her appeal was finally granted. However, the obstacles didn’t end there: “I didn’t have the same range of career options as I might have had, had I either stayed pretending I was a guy, or if I was a proper cis[gender] woman. Instead, I’m trans and nobody knew what to do with that,” Kolakowski explained. 

In the late 1980s, while Kolakowski was personally enduring rampant transphobia, the United States’ policies regarding transgender rights were in a state of disarray. The AIDS epidemic had begun, drastically setting back already-prejudiced attitudes towards LGBTQ+ people throughout the country. Furthermore, transexuality was considered a psychiatric disorder by the Diagnostic and Statistical Manual of Mental Disorders. In 1984, the U.S. Court of Appeals deemed that the Civil Rights Act of 1964 did not protect transgender people from discrimination; it wasn’t until 2020, with the Supreme Court case Bostock v. Clay, that employees were protected against discrimination for being transgender. Undoubtedly, the 1980s were a dangerous time to come out as transgender. 

In spite of the barriers Kolakowski faced, she managed to carve out an incredible law career for herself. “I eventually became general counsel of a small tech company [Telegen Corporation], and [then] went to work for the State of California as an attorney,” Kolakowski said. 

Kolakowski later returned to school to receive a masters degree in divinity—she became an ordained minister for the Metropolitan Community Churches, a majority queer congregation. Her desire to study religion stemmed from her lifelong pursuit to understand life’s meaning. While Kolakowski grew up in the Roman Catholic church, she didn’t fully develop her faith until later in life: “Growing up, I wrestled with how a loving God could have allowed me to live with this gender dysphoria. I prayed every day to wake up the next day a woman. I just didn't expect it to take as long as it did,” Kolakowski reflected. Looking around her office, Kolakowski commented on the intersection of physics and divinity in her life: “With my physics books over there and my religious books over here, somewhere I have the answers to all of life’s mysteries in this room, but I just don’t know how to figure them out.”

Kolakowski’s foray into divinity marked her fifth graduate degree (the others being biomedical engineering, electrical engineering, law, and public administration). Reflecting on her numerous degrees, Kolakowski concluded that she just really enjoys school, joking that she’s in “20th grade.” “[In university,] you have a curriculum, you have a syllabus. [...] In [a] world where people didn’t want people like me around, there was something reassuring about being part of an environment where I did well,” Kolakowski explained. 

Soon, Kolakowski’s career aspirations pivoted yet again: with her sights set on becoming a judge, Kolakowski launched her judicial campaign in the late 2000s. “I ran for an open judicial seat, twice. I was stomped in 2008 and ran again in 2010 and won,” Kolakowski explained. 

Upon winning her judicial election, Kolakowski was faced with the challenge of balancing her ministry and judicial roles, two careers that demanded major amounts of time and diametrically opposing expectations.“[My professions] were not just jobs—they were roles one had in society. You’re on 24/7,” Kolakowski described. “As a minister, I was expected to say something about everything going on in the world, and as a judge I was expected to say nothing about anything, so they were kind of at odds.” Ultimately, Kolakowski decided that she couldn’t continue her career as a minister while also serving as a judge. 

However, while juggling judicial responsibilities, Kolakowski has remained dedicated to educating others about LGBTQ+ legal issues, even on an international scale. “I’ve talked to people in India, Brazil, France, Colombia, Israel, and Poland,” Kolakowski recounted. She also works as an adjunct law professor, teaching a course in the intersectionality between equality rights and religious freedom. 

Recently, Kolakowski finished a two-year judicial assignment in Alameda County’s housing court, the county department that oversees trials regarding eviction and tenant complaints. “The thing that I am proudest of as a judge would be [handling the end of the eviction moratorium in Alameda county].” During the COVID-19 pandemic, an eviction moratorium was instituted in counties throughout the country to protect renters from losing their homes. However, when this legislation expired in April 2023, housing courts were overwhelmed with tenants being evicted from their homes. “We’ve been slammed with hundreds upon hundreds of eviction cases every month, two to three times the high amount prior to COVID-19. A lot of what I’ve been doing over the past two years is helping to work through that transition,” Kolakowski explained. This turned out to be an extremely challenging—though rewarding—task. 

Looking back on her time at Stuyvesant, Kolakowski expressed her admiration for her classmates’ intelligence and drive. “I was the first person in my family to go to college,” Kolakowski said. “Being around so many smart people allowed me to ask, ‘What can I be? How do I get there?’” However, Kolakowski also feels regret about not being able to experience Stuyvesant as her authentic self. “I’ve written off that part of my life because I wasn’t really me. [...] I didn’t go to Stuy, he did,” Kolakowski explained. 

Victoria Kolakowski lives a life that transcends all labels and limitations; she has immersed herself in learning through every facet of life, gaining expertise in engineering, law, and religion while also maintaining a happy marriage. Kolakowski’s path has certainly not been easy, but there is no doubt that she has ultimately had a positive impact on the lives of LGBTQ+ people around the world. While unable to attend Stuyvesant as herself, Kolakowski has certainly made the school proud to call her an alumna.