Westchester Casualty

Westchester Digital provides a traditional binding solution for property and casualty risks for small to mid-size businesses through a network of select wholesalers with delegated underwriting authority.

Westchester Environmental

Westchester News and Announcements,

Westchester leadership, executives

About Westchester

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Westchester is the Excess and Surplus specialty product group within Chubb that serves both the large corporate, middle and small market segments.

Chubb appoints **Dave Roberts** as the new president of **Westchester**, replacing **Lupica**, who transitions to executive chairman. Roberts previously served as Westchester’s chief operating officer (COO). The move follows Chubb’s restructuring of its insurance operations.

Aug 2026CoveragerNews article

Westchester Insurance Group names Tim Antonov as the new leader of its property and inland marine division. Antonov has worked at the company since 2012, bringing institutional expertise to the specialized insurance segment.

Sep 2025CoveragerNews article

Westchester has named Alex Faynberg as the new Head of Healthy Paws, a pet insurance provider acquired by Chubb in a deal valued at approximately $300 million. The appointment follows Chubb’s acquisition of the company, positioning Faynberg to oversee its operations within the larger insurance group. Healthy Paws specializes in pet insurance coverage for owners seeking financial protection for veterinary care.

Feb 2025CoveragerNews article

Chubb’s Westchester office launches three specialized business practices to refine its insurance offerings. The move follows leadership appointments to guide these new units, though specific roles or practice areas remain unstated. The restructuring aims to enhance operational focus amid evolving market demands.

Jan 2025Reinsurance NewsNews article