About Us

Our Story - Building a Legacy Since 1940

In the picturesque town of Jackson, Alabama, USA, a remarkable journey began in 1940. Skipper Insurance and Realty came to life through the vision of two visionary brothers, George W. and Harold D. “Bittie” Skipper. Their story is one of warmth, dedication, and a profound commitment to their community.

A Family Legacy

During the tumultuous years of World War II, George and Bittie entrusted the agency to the capable hands of their mother, Catherine Gaynor Skipper, and their sister, affectionately known as “Coo” Skipper McLeod. This unwavering family support laid the foundation for our enduring legacy.

The Next Generation of Visionaries

The transformative decades of the 1960s and 70s ushered in a new generation. George W. Skipper III, Joe C. Skipper, and Judy Skipper Slayton brought their unique perspectives, infusing the family legacy with fresh energy and innovative ideas.

Expanding Horizons

In 1984, Judy ventured to Birmingham, becoming a cherished part-owner of Glenn & Co., further enriching our narrative. Though the poignant passing of Mr. George Skipper in 1987 left a void, George III and Joe took up the mantle, nurturing growth and building a trusted reputation for insurance and real estate solutions.

Embracing Growth

The Skipper family continued to expand. Richard C. Skipper joined in 1992 as a producer, followed by David O. Skipper in 1999, who soon became an integral part of our daily operations. In 2008, David O. Skipper assumed the role of President, with Richard as Vice President, guiding us into our next chapter.

The Legacy Continues

In January 2022, we mourned the loss of George W. Skipper III, a reminder of the lasting impact he made. Joe C. Skipper, a stalwart since the 1980s, contributed his real estate expertise to lead us toward success. His daughter, Courtney Skipper Reeves, joined in 2017 as a licensed real estate agent, ensuring the family’s legacy endures.
Our story continued to evolve in 2021 with the addition of David O. Skipper’s daughter, Mary B. Skipper. By 2022, she had become an active, licensed insurance agent, proficient in property & casualty as well as life & health, symbolizing our ongoing commitment to exceptional service.

Over 80 Years of Dedication

Skipper Insurance and Realty has etched its name into the community’s heart for over eight decades. We embody qualities of dedication, integrity, and an unwavering commitment to serving others.
Join us as we continue this extraordinary journey, where family and community unite to make a difference.
Ready to experience the Skipper difference? Contact us today! 

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