This is not a story about Diamond Jim Brady (1856‒1917), who, during America’s Gilded Age, was a flamboyant, legendary businessman and philanthropist with an appetite for diamonds and other jewels. It is instead about Big Jim Brady, who, during America’s Gilded Age, was known for his own type of philanthropy, had an affinity for jewels, and was a legendary figure—as the handsomest and coolest of crooks.

Big Jim is a tough subject to tackle. From a young age, he was cool, slick, and secretive about his activities, leaving an intermittent and very difficult path to trace. Adding to the challenge—4 different ages applied to him spanning 24 years, 4 birth sites, and 4 aliases, besides the many identities he briefly “borrowed” from others. And just for good measure, top it off with three other well-known Jim Bradys from the same era.

Thomas Byrnes, one of the greatest police detectives in American history, wrote that Brady was a native of Troy, New York. He did have close friends and criminal consorts in that area, and family as well. One of his nicknames was “Albany Jim,” leading many to believe he was from Albany. Others placed his birth at Fairfield in northern Vermont. At any rate, he frequently spent time in the North Country.

In his youth, Jim apprenticed under his father, who was a jeweler and clockmaker. In the process, he became an expert machinist, creating specialized tools for the intricate work required in the trade. And laying the foundation for a decidedly unorthodox future.

After leaving the family business in his mid-teens, Jim hired on at a grocery, where his criminal leanings first became evident when he forged signatures to steal from the store owner.

Brady’s next documented crime was atypical for him because it involved physical violence. He was arrested in New York City in 1865 for a highway robbery that had occurred in Cohoes. He was brought north to face charges, but by returning much of what was stolen from the badly beaten victim, Brady avoided prosecution.

In Troy, he became close friends and literally a partner in crime with the infamous Pete Curley, saloon operator. Their gang of thieves and bank robbers kept North Country and New England lawmen busy for years, a time during which “Albany Jim” developed his preferred methods of robbery. For the handsome, blue-eyed, 6-foot 2-inch Brady, coolness, charm, and deception were the keys to success, and he was a master of all three. Threats of harm were sometimes used, but physical violence was a last resort. Brady’s penchant for thorough planning made him successful, which in turn kept him out of the headlines. Only those who got caught received media attention.

Throughout the 1860s, he doubtless committed many crimes and developed his abilities, for in 1869, he partnered with several of the country’s top thieves in a major bank robbery. Had he not been considered their equal, Brady would not have been part of the team.

In developing a plan for robbing Ocean Bank of New York City, they settled on renting the building’s basement for use as a money exchange. Under cover of remodeling the work area, they constructed a partition, behind which they began cutting upward into the stone floor of the bank.

On a weekend, the final plan was executed. With the expertise of men like Brady, they managed to open vaults and make off with quantities of cash and bonds. As so often happened, many of the bonds were useless, but cash, plus gold and silver, made the effort worthwhile. The booty of an estimated $60,000 equals about $1 million in 2013.

Among hundreds of criminals well known nationally, Brady fell within the small group at the top, the thinking men who understood the importance of preparation. He prepared to earn a steady income by planning most of his crimes thoroughly, and he prepared for a family future by purchasing extensive real-estate holdings in New Rochelle on the Long Island Sound.

Top criminals routinely joined forces on certain jobs, but when Brady distrusted a plan, he opted out. Conversely, despite a reputation for planning, Albany Jim was considered by lawmen and cohorts alike as the most daring of criminals. In that exclusive group, few if any were ballsier.

For evidence—and there’s plenty of it—consider Jim’s next high-profile job: a hit on the Kensington Savings Bank in Philadelphia in February 1871. One of the gang dressed as a policeman and visited the bank, informing officials that a robbery was pending. With their cooperation, police would provide extra guards that night to ensure catching the criminals in the act. The bank security staff was briefed, and everyone was sworn to secrecy, lest the crooks learn of the plan.

It took major-league cojones to attempt such a ruse. Several men were later named as the lead impersonator, but top lawmen like Byrnes and Pinkerton, along with other criminals, said it was smooth-talking Big Jim Brady, the actor extraordinaire, who pulled it off.

That night, two watchmen admitted the “policeman.” One fake cop, supposedly sighting the robbers outside the bank, took a watchman to pursue them. Meanwhile, the men inside tied and gagged the other watchman, doing the same to his partner when he returned. The gang then had the run of the bank, walking off with today’s equivalent of $1.2 million.

Brady’s good looks and suave demeanor served him well, especially where he wasn’t known, like Canada. In years past, a trip to Quebec (he spoke French) had proved very lucrative, as described by Brady years later: “Up in Canada? Oh, that was easy, except that often I’d nearly spoil it by laughing. I arrived in Montreal looking like a lord. Went into the best hotel. Who was I? I was the United States Internal Revenue Commissioner, that’s all.

“I went everywhere: banks, stores, government offices. When I got tired of Montreal, I went to Quebec City and then to Three Rivers. It was the same everywhere. They couldn’t do enough for me. And everywhere I went, I was making my plans. I had my gang always in the same town. I’d be the US Commissioner in a bank in the afternoon, and that night my boys would crack it and get all the stuff. It was too easy.”

Next week, Part Two: Hitting the Big Time.

Photos: New York World, 1900; Cleveland Leader, 1871; Titusville Morning Herald, 1871