Naval Academy graduate Cassandra Williamson served for more than nine years in the military, first as an enlisted Navy cryptologic tech collecting intelligence for a submarine group, and later as a Marine Corps officer. Today, she is the executive director of the Transgender American Veterans Association (TAVA) and continues her service by helping Veterans access care and benefits.

Williamson was born in eastern Kentucky but spent most of her life in Alabama. In 2022, as TAVA’s engagement director, she toured most of the major VA medical centers across the country and met many Veterans and staff.

“The national VA would help me open the door to all the VA facilities where I was going,” she said. “It was really a good time to be out there and see the Veterans.”

She recalled joyfully “getting the wind squeezed” out of her in Texarkana by a transgender woman Veteran.

“Rarely do we get to interact with another trans-Vet, and we feel slightly alone out there,’” she said.

During the trip, Williamson and TAVA President Ann Murdoch were among over 200 LGBTQ leaders invited to the White House for Pride Month. Williamson had traveled a long personal journey to enjoy that honor. She enlisted in the Navy in 1976, as part of a high school delayed entry program. She wanted to prove to her dad and herself that she “was his real male son,” though she had identified more as female since age five. But when she left for active duty in 1977, she knew her name was Cassandra.

“The name is from Cassie Williamson, in honor of my great-great grandmother, from the backwoods of West Virginia,” she explained.

Williamson served as a cryptologic technician from 1977 until 1980, an experience she said she enjoyed. Assigned to the Naval Security Group, she recalled sleeping in the torpedo room on one sub she was collecting intelligence for because she wasn’t a part of the regular complement.

“No room at the inn,” she chuckled.

She was sent to the Naval Academy prep school, where she was a battalion commander, before continuing to the academy. At the end of four years, to still identify with her “male side,” she became a Marine Corps officer and was assigned to a training command.

Williamson left the service in 1986. Since then, she owned various businesses, married, and had four children. She also entered public service. Nine years after her divorce in 2000, she began a medical transition, and she became more involved with her local VA, serving on Pride committees and participating in a pilot “Pride in All Who Served” program created by clinical psychologist Dr. Tiffany Lange.

“She’s wonderfully charismatic and engaging in thinking about how we can create resources for the [transgender] community, and that’s a professional passion of mine as well,” Lange said.

Around 2018, TAVA asked Williamson to join its board of directors. Being outgoing, she “took TAVA on the road,” meeting Veterans across the country. Often, Veterans would offer a place for her to stay, or money to cover gas.

“Veterans loved it. Everywhere I went, they wanted to give me a big bear hug,” she said.

After the road trip, Williamson became TAVA’s executive director. She promptly found an ambassador program on TAVA’s books she wanted to help stand up. The program’s goal is to “connect Vets locally right where they [are]” with resources, including housing, food and employment. Additionally, LGBTQ Veterans who were separated under the “Don’t Ask, Don’t Tell” policy, in effect from 1994 until 2011, could receive help upgrading their discharges.

“If this was the only reason the Vet was kicked out, this corrects that mistake,” Williamson said. “It improves the employment status for a lot of Vets and improves their care.”

After TAVA ambassadors are trained and confirmed by the board, they will travel to help Veterans in person. “Just like I did when I was touring the country,” she explained.

Despite her past challenges, Williamson enthusiastically encourages LGBTQ youth to join the military, if they want, especially now that they can do so openly.

“With the way you can come in as LGBT and still get in, it is the best way to get the life skills and the structure you might need to be successful, and it’s well worth it,” Williamson said. “For me, it’s a calling and obligation to serve.”

We honor her service.

Nominate a Veteran

Do you want to light up the face of a special Veteran? Have you been wondering how to tell your Veteran they are special to you? VA’s “Honoring Veterans” social media spotlight is an opportunity to highlight your Veteran and his/her service.

It’s easy to nominate a Veteran. Visit our blog post about nominating to learn how to create the best submission.

Writer: Trinity Green

Editor: Tayler Rairigh

Researcher: Raphael Romea

Graphic Designer: Kiki Kelley


Writer: Philip Van Slooten

Editors: Marisa Bunton, Cynthia Xu

Researcher: Christopher Rosenquist

Graphic Designer: Jaylon Buckles

Link Disclaimer

This page includes links to other websites outside our control and jurisdiction. VA is not responsible for the privacy practices or the content of non-VA Web sites. We encourage you to review the privacy policy or terms and conditions of those sites to fully understand what information is collected and how it is used.

Statement of Endorsement

Reference herein to any specific commercial products, process, or service by trade name, trademark, manufacturer, or otherwise, does not necessarily constitute or imply its endorsement, recommendation, or favoring by the United States Government, and shall not be used for advertising or product endorsement purposes.

Leave a comment

The comments section is for opinions and feedback on this particular article; this is not a customer support channel. If you are looking for assistance, please visit Ask VA or call 1-800-698-2411. Please, never put personally identifiable information (SSAN, address, phone number, etc.) or protected health information into the form — it will be deleted for your protection.

More Stories