On July 21, 1873, Jessie James and the Younger brothers successfully engaged in the first of many train robberies. This was the start of a long and notorious career for these men, many of whom would die violently in their single-minded pursuit of wealth. However, if they were alive today, I think that these enterprising businessmen would have made a different career choice; in fact, I am confident that they would all have become CEO’s of poorly-run Wall Street brokerage firms and incompetently-led insurance companies. After all, from a monetary standpoint, there is little difference between outlaws boarding a train, holding the passengers hostage, and then absconding with loot, and corporate executives going before Congress, holding the country ransom with the threat of economic collapse, and then looting the public treasury, including large bonuses for themselves. No difference, that is, except that in the latter case the risks are far smaller and the profits immensely greater.
Seen in this light, to vilify the James and Younger boys as criminals is completely misguided. Rather, they should be understood and praised as financial visionaries who exploited untapped revenue streams in unconventional ways, took considerable risks in the marketplace, and thereby demonstrated what the entrepreneurial spirit is capable of when unfettered by unnecessary and restrictive government laws and regulations. After all, as one sage put it, “the business of America is business,” and in that regard, these unjustly persecuted men are in truth heroes of commerce and poster boys for free enterprise at its best.