Did any Old West outlaw find that crime did pay?

Justin Loughmanr

Rancho Santa Margarita, California

Quite a few cow thieves wound up becoming big ranchers by “stealing a start,” while some small-time crooks wound up owning prosperous businesses. So-called “King of the Frontier Con Men” Jefferson Randolph “Soapy” Smith, a gangster and crime boss, became rich—but he was shot and killed at the age of 38.

During the 15 years the James Gang was active, they stole an estimated $200,000, yet Jesse James’s assassination left his family destitute. Like most of his ilk, Jesse was a big spender.

After Emmett Dalton got out of prison, he headed for California where his notoriety enabled him to make connections and make a fair amount of money in real estate and the movies. Al Jennings, one of history’s most inept train robbers, did the same thing.

But as far as famous outlaws becoming rich at their trade, and living long enough to enjoy it, they were as scarce as horseflies in December.