(Photo by Dylan Todd)
Kassanndra Santiago is a remarkable cultural curator, organizer and community builder whose unique contributions have profoundly shaped Central Florida’s social landscape. Their work exemplifies the power of storytelling and communal listening, bridging gaps between diverse communities and fostering connections that uplift the most marginalized.
Since 2019, Kassanndra has harnessed the potential of digital storytelling and resource-sharing through the @MyPineHills platform, skillfully uplifting and connecting underserved neighborhoods. They have pioneered grassroots leadership online, building trust and solidarity neighborhood by neighborhood.
With humility, compassion and an unwavering commitment to the community, Kassanndra consistently champions those who are often overlooked. This endeavor landed them a contributing journalist position for The Midtown Press.
Kassanndra is a fierce voice for low-income communities, queer and transgender individuals, disabled community members, and Caribbean and Latin populations. As a nonbinary, biracial leader of Afro-Caribbean and Mexican descent, they navigate and challenge systems that were not built for them, embodying resilience and authenticity at every turn — even when it angers others, she stands on business.
Their neurodivergent perspective informs a critical, level-headed and strategic approach to leadership, rooted in a Marxist philosophy that empowers them to not just participate in the community but to actively shape its future.
In their leadership roles, Kassanndra served as governance co-chair on the Contigo Fund Steering Committee, where they learned the importance of community-centered strategies, and as a member of Orange County’s Disability Advisory Board.
As the current president of SOMOSLOUD Central Florida, Kassanndra continues to make significant strides in the crucial fight for HIV stigma and decriminalization. Their work emphasizes intersectionality, amplifying the voices of queer and trans people of color while fostering a sense of belonging.
Last year, Kassanndra faced serious health challenges that brought them to the brink. Yet, they emerged from that experience not only with renewed strength but also with a profound sense of purpose, continuing to serve as a thought leader and community anchor despite critical illness. Their commitment to the community shines through the noise, earning them a recognition from the City of Orlando for their community service that same year.
Currently, Kassanndra is spearheading the inaugural LGBTQ+ Town Hall for Pine Hills and West Orlando as the co-executive director of Development for Las Semillas — leading a pivotal moment for visibility and the amplification of voices in this minority majority area. They lead not from titles but from lived experiences and heartfelt connections.
Kassanndra doesn’t just serve the community; they too are the community. That framework of relationships has no hierarchies. They are beside you.
Kassanndra Santiago stands out as a truly remarkable person deserving of recognition, not only for their unapologetic support and warmth but also for their transformative impact on our community. Their innovative approach to building bridges and fostering inclusivity challenges us all to listen, learn, and engage more deeply with one another. They are kindness and a spoonful of tough love.
View the full list of Watermark Out News’ Remarkable People of 2025 here.
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