Andrew J. Windsor: Attorney, Artist, Advisor

Andrew J. Windsor (“Drew”) is an attorney, artist, and advisor from Southern Brooklyn, New York City.  

Born and raised in the neighborhoods he still calls home, Drew has built an unconventional path spanning law, government, public service, business, and the creative arts. Across these pursuits, his work has been shaped by a curiosity about people, institutions, and the communities that bring them together.

That path began creatively. His early YouTube channel reached half a million views through 'infotainment' content that blended information and entertainment, later evolving into mural art, comedy skits blending humor and social commentary, and social media posts highlighting resilience and real-world challenges including hardship, homelessness, and unemployment.

Drew stayed local for his education, choosing New Utrecht High School over Brooklyn Technical High School despite excelling on the specialized high school exam, a decision highlighted in the New York Daily News for its focus on staying connected to his community. 

At New Utrecht, he was active on the wrestling team and in school productions before being elected Senior Class President. In that role, he led initiatives such as introducing the school’s first mascot in a century, promoting school spirit through organizing school merchandise sales, and collaborating with other local high schools on a documentary aimed at helping middle school students transition into high school. He also served on the School Leadership Team alongside parents, teachers, and school administrators, and as a student representative on the District 20 Community Education Council, gaining early experience in educational policy, community advocacy, and local government.

An honors graduate of CUNY Baruch College, Drew was active in student government by successfully amending the school constitution, and contributed articles to the school newspaper defending free speech on campus. He later expanded his global perspective by studying abroad in China, immersing himself in the local business and culture of Beijing, Nanjing, Shanghai, and Xi’an. 

After graduating a year early from CUNY, Drew was awarded the Colin Powell Fellowship in International Diplomacy. Through the fellowship, he served with the White House Liaison at the United States Department of State and held a Secret security clearance. He later returned to Brooklyn and lobbied for public safety legislation in New York City, furthering his interest in the intersection of law, government, and community advocacy.

As a Dean’s Scholar at Yeshiva University’s Cardozo Law School, Drew brought together a diverse group of elected officials for a public discussions on the 2020 Census, focusing on the importance of ensuring that New Yorkers were counted and represented. He was later was elected student government president, where he worked towards an in-person graduation during the COVID-19 pandemic to bring students and their families together for celebration. Throughout law school, Drew remained active in his hometown of Brooklyn, organizing an event honoring veterans to recognize their service and contributions to the community. 

After receiving his law degree, he went on to serve as a private real estate attorney, where he worked with everyday New Yorkers to achieve the American Dream of homeownership, and as Associate Counsel for the New York State Senate, where he gained experience in legislative processes from municipal finance and New York City government to gaming, elections, and economic development.

His work in government reinforced a philosophy that has guided much of his public service: government works best when it remains accessible to the people and communities it serves. 

Back home in Southern Brooklyn, Drew continued that work at the neighborhood level. He served as Secretary of Brooklyn Community Board 11 and as Chair of the Neighborhood Advisory Board representing Bath Beach, Bensonhurst, and Gravesend.

Through his community and civic involvement, he has worked with residents, local organizations, businesses, government agencies, and elected officials on issues affecting the neighborhoods where he grew up.

For Drew, public service has remained rooted in the same communities that shaped him, connecting the work of government with the everyday concerns of the people it represents.

Currently, Drew is focused on expanding Windsor Services LLC, focused on waste management, property cleaning and maintenance, and property management, as well as Pensieve Strategies LLC, an independent consulting firm providing strategy, messaging, outreach, and implementation support to campaigns, nonprofits, and small businesses. 

Through these ventures and his continued civic involvement, Drew remains focused on supporting small businesses, strengthening neighborhoods, encouraging economic development, and finding practical solutions to the challenges facing New York City.

Beyond his professional and civic work, Drew maintains a diverse range of interests and affiliations. He is a member of the LGBT Bar Association of New York, NYC Bird Alliance, The Society of American Magicians, and Greater New York Mensa, and continues to develop his Indonesian and Malay language skills.

Drew continues to live and work in his hometown neighborhoods of Bensonhurst and Bath Beach in Southern Brooklyn, New York City. His work and initiatives have been featured by media outlets including the New York Daily News, NY1, and News 12, while his artwork has been exhibited or published through Greenpoint Gallery, Encounters Magazine, and the Brooklyn Streetcar Artists Group (BSAG).