John McDonald (Union army general)

To support himself, McDonald worked a series of odd jobs on canals, lakes, and rivers.

Eventually, he started his own business, running a freight steamer that carried passengers on the Missouri River.

In October 1869, President Ulysses S. Grant appointed McDonald Internal Revenue Collector of the Missouri District headquartered in St. Louis.

McDonald organized an illegal racketeering operation known as the Whiskey Ring, profiteering by depleting the Treasury of tax revenue.

Found guilty, McDonald was fined $5,000 and sentenced to serve 18 months in federal prison.