Thomas Earle Gentry was born in 1896, a few miles north of Montgomery in Montgomery County. As a young boy he attended a small country school in that area, but most of the teaching he received was from his mother at home from school books she had received from a cousin in North Carolina.

He never attended high school, because there wasn’t one. He did, however, pass entrance exams and was admitted to Sam Houston Normal in Huntsville. After college he taught school briefly in Williamson County and in North Montgomery County.

He served his country as an enlisted man and as an officer in the United States Army. He served in Europe in both World War I and World War II.

In 1923 he married Iola Everett of Conroe, whose father had founded Everett & Sons. He and Iola had one daughter Anne, who became Mrs. Lavoy Moore. He acquired an interest in 1924 and was with Everett & Sons for 16 years. He opened his own business –Gentry’s Men’s Shop- on September 9, 1939.

Earle was one of the early volunteers of the Conroe Volunteer Fire Department and was elected Fire Chief in 1929.


  • Elected to Conroe City Council, 1930
  • Elected Mayor of Conroe, 1938, 1940, 1942, 1948
  • Charter member if the Conroe Chamber of Commerce, 1934
  • President of the Conroe Chamber of Commerce, 1937
  • President of Rotary Club and member for 53 years
  • Member of First United Methodist Church