Andrew J. Windsor: Actor, Artist, Attorney

Andrew J. Windsor, also known as “Drew,” is a multi-faceted professional whose career encompasses art, acting, law, and entrepreneurship. His path reflects a commitment to creativity and purpose, with each step marked by resilience and a vision for betterment.

Born on the cusp of both the Millennial and Gen Z generations, Drew’s formative years were shaped by events that influenced his worldview. His earliest memories include witnessing the emotional impact of 9/11 on his mother as she cried during the terrorist attack on her workplace in the World Trade Center. This moment profoundly shaped Drew’s empathy and drive.

He turned to art and humor as creative outlets, exploring digital storytelling on YouTube during its early days from 2007 to 2009. By age 13, he had reached half a million views by combining information and entertainment to create “infotainment” tutorials on new social media platforms like Facebook. Although he paused content creation soon after, Drew left his channel up to inspire young creators with a message of perseverance and creative exploration.

Drew’s artistry continued through high school, where he designed murals and hosted talent shows. He produced and acted alongside other Brooklyn students in a YouTube skit channel called “The So Inappropriate Show.” Through humor, he addressed complex social issues like homophobia, sexism, and racism, often pushing boundaries with skits such as “Al Gayda,” a satire tackling anti-terrorism through comedic stereotypes. By 2015, Drew shifted his focus to law and politics, seeing these as paths to meaningful change.

During the pandemic, Drew returned to art under the name 4drew2draw, creating paintings that reflect his love of nature and edited photography exploring themes of love, travel, and growth. In 2024, he debuted “Drew Drives Downtown,” a psychological thriller tragicomedy short film shared privately via Instagram Stories. This powerful return to storytelling explored his journey as an LGBTQ attorney, delving into themes of political and familial betrayal, mental health misdiagnosis, and the realities of homelessness and unemployment.

Drew’s dedication to public service began early. A proud graduate of our New York City public schools, Drew chose to attend his mother’s alma mater, intending to be involved nearby in the local communities of Southern Brooklyn, and declined acceptance into specialized high school in Northwestern Brooklyn. There, he engaged deeply with his community, from interning with local elected officials to managing a summer camp for local youth and working for an amusement park company. Active in school life, Drew joined the wrestling team and was elected Senior Class President. He led initiatives such as implementing the school’s first mascot in a century, building school spirit through merchandise sales, and collaborating with other high schools to create a documentary aimed at helping middle school students transition to high school.

As a proud City University of New York (CUNY) undergraduate, he represented students in student government, wrote for the school newspaper, and broadened his perspective through study abroad in China, where he immersed himself in the local business, educational, and cultural scenes for a month in 2018. Later, at Benjamin N. Cardozo Law School under Yeshiva University (YU), he was elected student government president, where he led a public discussion on the 2020 Census with over a half-dozen elected officials. His experiences with City agencies during this time gave him firsthand insight into how government fines and policies impact New Yorkers.

After graduating amidst the pandemic, Drew began his legal career as a volunteer attorney defending low-income homeowners against fines from the New York City Department of Buildings. He later served as a real estate attorney, helping families in Brooklyn achieve homeownership. As Associate Counsel for the New York State Senate, Drew handled areas such as gambling policy, government contracts, and election law, gaining significant insight into municipal finance and public service. Known for his collaborative approach, he has worked with allies across diverse backgrounds and affiliations, consistently striving to make government more accountable and transparent.

After earning his law degree, Drew founded Windsor Services LLC in his mid-20s, growing the business into a recognized firm within New York City’s property management and real estate industry. As a small business owner, he knows the importance of alleviating bureaucratic regulatory burdens and promoting expansion of small business in our communities. 

He is now dedicated to pursuing technological innovations across various industries, driven by a vision of progress and impact, while also preparing to release his first book.

Drew’s work and initiatives have been featured in various media outlets, including the New York Daily News, NY1, and News12.