>>3988303
Tax law would have been extensively different when he was alive. Baby America initially only taxed imports through tariffs, whiskey, and apparently glass windows. States and localities did poll taxes (pay us to vote) and property taxes (land and commercial buildings). Inheritance taxes began in ~1900 and states started collecting sales taxes in the 1930s (which seems like a dick move considering the Depression). Income tax began temporarily during the Civil War (funding the Union so it wouldn't have been established in Lousiana) but became a permanent fixture in 1913 with the 16th Amendment. Capital gains taxes were also included at this point (7%).

>Revenue Act of 1913, levying a 1% tax on net personal incomes above $3,000
>yearly salary for a radio personality in the 1920s ranged between $2,600 and $5,200
>depending on station, popularity and experience

In the 1930's (1933-1938) FDR's New Deal reforms would have introduced a payroll tax.

My cursory Googlefu didn't turn up anything in how anal enforcement was. If it was tightly enforced he might have paid it to keep the authorities off his back. If it wasn't he probably avoided paying taxes as much as possible.