History

Peel & Holland traces its roots back to 1924 when Dwight R. Peel formed D. R. Peel & Company. Mr. Peel had one employee until he hired Woodrow Holland in the late 1930s. Mr. Holland’s insurance career was interrupted by a tour in the U.S. Navy during World War II.

A few years after Woodrow’s return from the Navy he became a partner, and the name was changed to Peel & Holland Insurance. A short time later Mr. Peel died and Woodrow purchased the business from Mable Peel, Mr. Peel’s widow. No one ever envisioned this small-town business growing into one of the larger independent insurance agencies in Kentucky.

As the business began to grow, Charles “Tot” Jackson was hired by Mr. Holland in the early 1950s. On July 5, 1965, Woodrow hired R.C. Riley to join Peel & Holland. The agency now had three employees in addition to Mr. Holland, Mr. Jackson and Mr. Riley.

As the agency continued to grow, Mr. Holland, on January 1, 1969, sold a one-third interest each to Mr. Jackson and to Mr. Riley. In December 1977, Woodrow sold his remaining interest in the agency and retired.

After a long and successful career, Mr. Jackson retired in December 1980.

Helping the agency grow through the years were key employees and part-owners Pat Hurley, Brad Colson, David Moffett, and Joe Barnes.

After completing 41 years with Peel & Holland, then president and CEO of the firm R.C. Riley retired in 2005.

The present owners of Peel & Holland are Roy C. Riley III, Keith B. Riley and Gregory Carlton. Roy started with Peel & Holland after graduation from college in January 1991; Keith after graduation from college in May 1993; and Greg in August 1994.

Over the years, Peel & Holland has enjoyed significant growth in personal and commercial insurance, risk consulting and employee benefits with 40 employees doing business throughout Kentucky and in Southeast Missouri, Southern Illinois and Northwest Tennessee.