Irish-American entrepreneur and railroad financier James “Diamond Jim” Buchanan Brady


There have been many times in my life when a situation develops where I fear I am going to fail. Whenever the odds against me seem insurmountable or I cannot think of a solution, I remind myself of an individual who faced complete ruin after achieving tremendous success in a variety of business endeavors: railroad equipment and supply salesman, racing stable owner, railway car manufacturer, steel mill owner, farmer, stock speculator, philanthropist, and all around bon vivant and gourmand. Incredibly, this person did not plan to become any of these. Chance, happenstance, and equal portions of hard work and self motivation were his tools of success. 

 His name was James Buchanan Brady, though he was better known by his nom de plume “Diamond Jim” for his propensity of wearing enough diamonds in public so as to glitter like a French chandelier.  

Jim was born on August 12, 1856 above the saloon his father owned in the west side of Manhattan. He literally grew up around his father’s bar, observing how political deals and business arrangements were made. Then, in 1863, his father died suddenly. Though his mother quickly remarried, Jim did not get along with his new stepfather, who turned the bar into a dive and shanghai center. So at the age of eleven, Jim and his older brother Dan left home. Jim soon found employment at the elegant St. James Hotel as a bellboy. For the next few years he had a ringside seat in observing how the “other half” of society lived – industrialists, bankers, robber barons and kings of commerce all dressed to the nines, and always accompanied by equally fashionable ladies in the latest haute couture.

Always a bright and congenial person, Jim, by the age of 15, was given his first real career opportunity by one of the hotel’s regular patrons, John M. Toucey, an executive with the New York Central Railroad. Mr. Toucey made the following proposition: if Jim was willing to take a cut in pay to start in the baggage department and go to business college at night to study bookkeeping, he would be given an opportunity to advance himself.  Jim readily accepted.

By the time he was 21, Jim was made chief clerk and confidential right-hand man to Mr. Toucey, under whose tutelage Jim learned the inner secrets of the railroad business: organization, cost analysis, reliability performances of locomotive equipment, repair scheduling and just about anything related to efficient office administration. 

Then Jim was fired

 A few years earlier, Jim had managed to have his brother hired by the New York Central. Unfortunately, Dan was later caught raiding the petty-cash box. The accepted mores of the day dictated that Jim be discharged too. This was something John Toucey, now the General Manager, was reluctant to do. He genuinely liked Jim and he was also afraid that a rival railroad would hire him and thus be privy to New York Central’s corporate secrets – at the time the New York Legislature was about to begin a major investigation into railroad practices.

Toucey arranged an interview for his young assistant with his friend Charles Moore, a partner with Manning, Maxwell & Moore, a major railroad supply company. Even though Jim had no sales experience and his rough-hewn speech often included “dems” and “does,” Moore was won over by Jim’s genial nature and natural charm. That, and his extensive knowledge of railroad operations. He was hired immediately.
Before going on the road, Jim made certain that he was properly outfitted.  Recalling his days at the St. James, he knew that in order to make money you have to look like money, so he spent his savings on several hand-tailored suits, a stove pipe hat, a fur-collared overcoat, and a one carat diamond ring (which successful men of the day wore as a display of their credit rating and not as a frivolous adornment). When making a sales call it was not uncommon for Jim to be mistaken as a member of the board of directors and not some common “drummer.”

In no time “Diamond Jim” became the number one salesman in the country. He accomplished this by engaging in the sort of intelligence gathering normally associated with a secret agent. Before stepping into the purchasing superintendent’s office, Jim would spend days, even weeks, reconnoitering the railroad’s network right down to the tool shacks and the gandy dancers who kept the track straight. In other words, he got to know the men who really ran the railroads: section foremen, mechanics, stationmasters and conductors and he acquired all sorts of inside information as to equipment and repair shop needs and current and future requirements.  Jim would often know the needs of the railroad better than the executives and this was the reason for his success. He soon became wealthy enough to support his mother in a new house, now that his stepfather had abandoned her and headed west.