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T. Patrick O'Brien has a diverse work experience in the insurance industry. T. Patrick began their career at RSA in 1982, where they served as a Branch Manager and RVP for Royal Insurance until 1994. T. Patrick then joined Merchants Insurance Group in 1984 as a Branch Manager and RVP, and stayed with the company until 2001. T. Patrick O'Brien then moved to Hanover Insurance, where they worked as a Small Commercial Sales Manager from 2001 to 2011. In 2011, they joined The Barclay Group and J. S. Braddock Agency, initially as a Commercial Sales Manager before being promoted to Vice President in 2020.

From 1963 to 1965, T. Patrick O'Brien pursued a Bachelor's degree in Philosophy at St. Vincent College.