About Us

The Leading Independent Insurance Agency

Haywood and Fleming Associates is a leading independent insurance agency located in Gary, Indiana. The firm was established in 1984 by Roosevelt Haywood III, a second-generation insurance professional, who started in the business at an early age working in his father's agency, Haywood Insurance.

During its years of growth, Haywood and Fleming Associates has developed considerable experience in serving the insurance and risk management needs of large and complex commercial accounts. During this period, we have developed into a superior service provider for prominent private and public sector clients located in Northwest Indiana, Chicago and the suburbs.

Our ability to form effective partnerships with our clients, other industry professionals and the insurance companies underwriting the risk is our most significant advantage. The synergy from these relationships has allowed us to work at high levels of efficiency and effectiveness while producing many successful outcomes.

Who We Are

Roosevelt Haywood III - Agency Principal/Team Leader
Overall Account Administration

Leslie Skinner-Leslie, Agency Associate
Vice President of Marketing & Operations - Commercial Lines

Roosevelt Haywood IV
Agency Service Representative

Teena Arrington, Executive Assistant
Administrative Support