Augustus Casear Award | 2026

Jason A. Quaglia – Commercial Risk Management Insurance

Jason Quaglia carries his upbringing on Harlem Avenue as a badge of honor. Raised in the heart of Chicagoland’s vibrant Italian American neighborhood, he was immersed from birth in “Old World” values—principles defined by unwavering respect, fierce loyalty, and a deep-seated commitment to the collective good. These aren’t just cultural footnotes for Jason; they are the foundational pillars upon which he has built his life and a distinguished 17-year career in the insurance industry.

In an era of automated service and transactional business models, Jason stands apart by prioritizing human connection. He firmly believes that insurance is not just about policies, but about protection and peace of mind. Throughout his career, Jason has consistently demonstrated a “client-first” ethos, often forgoing short-term profit to ensure his clients receive the ethical guidance they deserve. To Jason, a handshake still signifies a sacred bond, and his reputation for integrity is his most valued
asset.

Specializing in complex commercial risks, Jason utilizes a creative, analytical approach to navigate the intricacies of the modern market. He doesn’t believe in “one-size-fits-all” solutions. Instead, he engineers cost-efficient programs that provide the broadest possible coverage at the most competitive price points. His deep industry knowledge spans several specialized sectors, including: Professional Services & Medical Malpractice, Real Estate Development & Management, Non-Profit Organizations, the Entertainment and Hospitality Industry

Beyond his professional life, Jason is a tireless advocate for Italian American heritage. He is committed to strengthening the cultural fabric of Chicagoland while building strategic ties both nationally and
internationally. Whether he is serving in a professional capacity or volunteering his time for local causes, his mission remains the same: “Support those who support the community.” When you partner with Jason, you aren’t just hiring a broker, you are gaining a dedicated advocate who treats your business like family.