Meet Josie
Josie is a small town girl.
A Latina, she and her sister were raised by a single mother and her grandparents. To make ends meet, her mother pulled double duty as a Head Start teacher and public bus driver. After her mother remarried, Josie gained her true father, a police sergeant, and her parents raised her and her sister to believe in work ethic and a tireless drive to push forward. Seeing her mother and father not just work hard, but work for their community, endowed Josie with a love of her country.
This sense of patriotism led Josie to join the U.S. Navy. She became certified as a nuclear power operator, deploying four times to hostile waters aboard the USS Ronald Reagan. After their service, they pursued their career in public service, which opened the doors to their life as an activist and political strategist. She has proudly served within the Democratic Party as a presidential national delegate, a founding member of the DNC Trans Advisory Committee, and also was recently appointed to serve on the Maryland Commission of LGBTQIA+ Affairs.
As a trans woman, Josie began living as their authentic self in 2020, embracing the truth of their identity. The reason for this is that Josie still believes America is a place where we must all be equal under the law, where living your truth is as American as apple pie, and where we can achieve if we set ourselves to big, bold goals that lift Americans out of poverty.
Now, Josie is running for Montgomery County Council at-large because this isn’t the time to step back, but the time to step forward, step up, and fight for what we believe in. This means fighting to build more housing, provide assistance to cut costs, and relief for renters, this means working to protect the local community from job losses caused by reckless federal spending cuts, this means working with public school teachers as our partners and allies in educating the future generations, this means embracing immigrant communities not demonizing them, and doing our part to fight the climate crisis by building green.
Josie lives in Silver Spring with her partner, Katie, and their dog, Annie.
Proudly Endorsed By:
Montgomery County Education Association
Montgomery County Education Association
Montgomery County Education Association
Union representing over 14,000 teachers and staff in the Montgomery County Public Schools system.
SEIU 32BJ
Montgomery County Education Association
Montgomery County Education Association
The largest property services union in the US, representing 185,000 members across 12 states and DC.
AFL-CIO Metro-Washington Council
Montgomery County Education Association
AFL-CIO Metro-Washington Council
Local council of the nation's largest labor federation. Connects over 150 union locals in DC and Maryland.
ATU Local 689
AFSCME Council 3
AFL-CIO Metro-Washington Council
Regional union with over 15,000 members working in public transit across Maryland, Virginia, and DC.
AFSCME Council 3
AFSCME Council 3
AFSCME Council 3
Storied public employee union representing over 50,000 workers in public service across Maryland.
CASA In Action
AFSCME Council 3
AFSCME Council 3
National organization with 155,000 members who mobilize Black and brown voters for progressive causes up and down the ballot.
Sierra Club
Working Families Party
Sierra Club
Environmental policy advocacy group with 3.8 million members nationwide and a chapter here in Montgomery County.
VoteVets
Working Families Party
Sierra Club
The first and largest group of Democratic Veterans in America. Backed by over 1.5 million veterans supporting candidates that support veterans and their causes.
Working Families Party
Working Families Party
Working Families Party
National progressive grassroots political party building a multiracial movement to build an affordable and just future for working people.
Progressive Maryland
Progressive Neighbors
Working Families Party
Statewide nonprofit advocacy organization with over 120,000 members who work to promote racial, social, economic, and environmental justice.
Progressive Neighbors
Progressive Neighbors
Progressive Neighbors
Volunteer grassroots political action committee focused on electing principled progressives to local office here in MoCo.
Montgomery County DSA
Progressive Neighbors
Progressive Neighbors
Charted branch of regional organization with over 2,500 members in Montgomery County, Prince George’s County, Northern Virginia, and DC.
LGBTQ+ Victory Fund
LGBTQ+ Victory Fund
LGBTQ+ Victory Fund
Organization supporting pro-equality, pro-choice, out LGBTQ+ candidates at all levels of government across the country.
Progressive Victory
LGBTQ+ Victory Fund
LGBTQ+ Victory Fund
National digitally-focused progressive organizing platform connecting volunteers across the country.
Our Revolution
LGBTQ+ Victory Fund
LiUNA Baltimore/Washington District Council
National progressive organization founded by Bernie Sanders to fight for a government that works for working people.
LiUNA Baltimore/Washington District Council
LiUNA Baltimore/Washington District Council
LiUNA Baltimore/Washington District Council
One of the nation's fastest-growing unions, representing essential workers across the US and Canada.
Kristin Mink
LiUNA Baltimore/Washington District Council
Michael L. Subin
Montgomery County District 5 Councilmember
Michael L. Subin
LiUNA Baltimore/Washington District Council
Michael L. Subin
Former Montgomery County Council Member, At-Large (1986 - 2006)
Josie in the News
Silver Spring resident Josie Caballero, an LGBTQ+ policy advocate and Navy veteran, says she is running for an at-large seat on the Montgomery County Council in the 2026 general election because it’s time to stand up and fight for the county in the face of changes wrought by the Trump administration.
Director of Special Projects at the National Center for Transgender Equality Josie Caballero joins Meet the Press NOW to discuss how companies are addressing pride campaigns and safety concerns.
There have been over 500 anti-trans bills introduced across the United States. Some of these bills are threatening to redefine the business landscape. These bills range from forcing customers to use specific bathrooms to attacks on employee retirement. If these bills were to be enacted, businesses and workplaces would be forced to change how they do business.
When Josie Caballero was 8 years old, growing up in Mineral Wells, Texas, she assumed every little boy secretly wished to be a girl. Caballero had been born the oldest male in a conservative Latino family. “In Latin culture, the first-born male child is kind of the person that leads the family,” she says. “So to turn all that around, and become the woman I’ve always been, was very hard on me.”
Born and raised in small-town Texas, growing up, I seemed like a pretty happy kid. I got A’s in school, played soccer, sang in the chorus, was in student government, and even started the chess club at my high school.