Caldwell started his career by working for his father's insurance company in the early 1910s. Caldwell founded his own insurance company, Caldwell and Company, in 1917. The firm invested in
bonds throughout the
Southern United States. His marketshare grew after
World War I by insuring construction company engaged in building infrastructure and roads in the South. The firm was a
depository bank for insurance bonds. Caldwell acquired "insurance companies, banks, textile mills, oil companies, department stores" throughout the 1920s. With politician
Luke Lea, he acquired banks and two newspapers,
Memphis Commercial Appeal and the
Knoxville Journal. (Lea also controlled the
Nashville Tennessean.) When
Henry Horton, Lea's friend and business associate, became
Governor of Tennessee in 1927, Caldwell and Lea received no-bid contracts to build highways in the state with their Kentucky Rock and Asphalt company. This became known as the "Kyrock Scandal." However, the company was declared insolvent later that year in the wake of the
Wall Street crash of 1929. Caldwell was sued in the Chancery Court of Davidson County, Tennessee in December 1930. He was also criminally
indicted by the states of Tennessee and Kentucky in 1931. but this ruling was overturned by the
Tennessee Supreme Court, and he was never
extradited to Kentucky. Nevertheless, his estate, Brentwood Hall, was taken from him by the state of Tennessee in 1957. Caldwell co-founded a new investment banking firm, Rogers Caldwell and Company, in 1932, with only
US$1,000. ==Personal life==