Leroy J. Thompson Sr.
A lifelong entrepreneur, natural leader and civil rights activist
(1912-1994)
“He was one of the greatest St. Mary’s countians in this century. He was a natural leader, a very wise person, who was often sought for counsel.” State Delegate John Slade, 1994.
Leroy Thompson’s mother was a teacher at the Drayden School and his father a farmer in St. Mary’s County, Maryland. As a young African American man, Leroy had to leave the county to attend high school. In 1928, he attended high school in Washington, D.C. When his dreams of college were thwarted by the Depression, he moved back to St. Mary’s County and established the Happyland Club in Valley Lee.
Mr. Thompson was a lifelong entrepreneur. In 1935, he developed a business that became known as Happyland. It was an entertainment venue and much more. The bar had vending machines and a juke box. He enlarged it to include a pool room, barber shop, beauty shop, a grocery store and apartments on the second floor.
Successful and well known in both the White and Black communities, Mr. Thompson and his brother Brent, built and opened a tavern in the 7th district in 1946, which also included a pool room, beauty and barber shop as well as upstairs apartments. He purchased a tavern in Leonardtown in 1954. Then in1955, he purchased a share in the Wicomico Inn, a 33 room beach hotel at Long View Beach.
Leroy never missed an opportunity to develop a potential business. Baseball was a very popular sport in St. Mary’s County both before and after segregation. Observing this trend, Leroy went into partnership with a Lexington Park businessman in1967, the business included a baseball diamond.
Leroy was a family man, business man, civil rights activist, and community builder. He served long terms on many commissions and boards, including the Board of Supervisors of Elections, Justice of the Peace, Housing Authority, Commission on Aging, and Home for the Elderly. When the St. Mary’s population outgrew the local segregated hospital, he was selected as a fundraiser for the “colored” people to build a new wing for the hospital. He served with the understanding that the hospital would no longer be segregated. Because of his successful fundraising, the new integrated Peabody Wing opened in 1965. Many praised his lifelong efforts to improve race relations in the county.
In his Slackwater interview, Mr. Thompson speaks of what life was like for African Americans in St. Mary’s County, especially as compared to whites. He talks about visits from Thurgood Marshall and other NAACP members and how he was involved with setting strategies for integrating the schools, and improving conditions for Black students and teachers in the county.
Though he did not run for office himself, he was politically active and influential and his support was valued by local and state candidates for office. He belonged to many social and religious organizations, including the Elks, Jolly Gents, Minority Business Alliance, NAACP, 4-H clubs, St. Mary’s County Fair Association and others.
“He touched so many lives. People get in trouble; they go to Leroy. He was a bridge throughout the community.” said Delegate John Slade.
Additional Resources
Leroy Thompson interviewed by Andrea Hammer, St. Mary’s College Maryland Slackwater Collection. https://smcm.contentdm.oclc.org/digital/collection/p4105coll5/id/250/rec/1
Leroy Thompson’s daughter Alma Jordon is interviewed about her father and the Happyland bar/community center:
