As noted in Part 1, Albany Jim Brady’s good looks and suave demeanor aided him on crime trips to outside areas, like Canada. To operate in more familiar haunts, like New York City, he became a master of disguise and used many an alias. Still, as skilled and shrewd as Brady was, his daring exploits are what often got him into trouble.

During a long career, he displayed an affinity for diamonds, and shortly after the Kensington Bank job, it was a foiled jewelry heist that landed him in the clutches of the law. For a month, Brady was held in The Tombs, Manhattan’s infamous jail. Then, in spring 1871, he was sentenced to five years in state prison. And off he went to the penitentiary at Sing Sing, later being transferred to Auburn in central New York.

There he developed friendships with other top men in his field, including Jimmy Hope and Dan Noble. Each was already well known in his own right. Acting together and individually, they would soon become the most celebrated criminals in the country.

In late 1872, that trio and a few other inmates were hard at work on an escape plan. The shaft of a water wheel ran through the prison’s south wall, which was several feet thick. Bit by bit, they worked through the solid concrete until only a thin layer remained. It was arranged to have civilian clothing outside the wall, and on January 3, 1873, the entire group exited through the hole, changed into street clothes, and simply walked away.

For Brady, it was the beginning of a highly improbable 14-month saga that added substantially to his notoriety. In mid-May, two New York City detectives were tailing one George H. Osborne, who they believed was planning to dispose of considerable booty: $30,000 in negotiable bonds (valued at about $600,000 in 2013). Unknown to the lawmen, “Osborne” was actually Jim Brady. The suspect was followed to the second-story apartment of a quack doctor, known to be part of the city’s criminal element.

The officers burst in, and Detective Tully proceeded to search the doctor in a separate room. Detective Dilks, one of the force’s top men, began questioning Osborne, who casually mentioned his thirst and moved to the water dispenser for a drink. Then, with a sudden move, he lifted the window open and jumped, dropping two stories to the sidewalk below. He was followed quickly by Tully, who was injured upon landing, and Dilks, who gave chase.

Osborne (Brady) was carrying two guns, but while running, he was unable to draw and fire. Dilks shot several times, once hitting a bystander, and one bullet striking Brady in the leg. Realizing the officer was gaining on him, Brady threw the stolen bonds away and jumped through a basement window, startling a family that was having dinner. Dilks followed, and Brady was eventually captured.

The discarded bonds were retrieved, linking Brady to robberies of banks in Glens Falls and Port Jervis, and another one or two in Ohio. In August, he was sentenced to three and a half years at Sing Sing (where he gave his name as James Morrison). When that stint was served, he would be shipped to Auburn for completion of the sentence he was serving when he escaped.

About a month later, Brady and a cohort bribed an officer, escaped from Sing Sing, and headed south. Only three weeks had passed when a gang was arrested in a failed bank robbery in Wilmington, Delaware. An officer from Sing Sing was summoned to provide positive identification, confirming that the captured crooks included Jim Brady and Jimmy Hope, plus two others.

They had entered the bank cashier’s home with guns drawn, but when one person escaped, the men fled and were captured the next night. All four were convicted and handed the same sentence: one hour in the pillory (stocks), a $500 fine, suffer 40 lashes, and spend 10 years in prison.

Protests were mounted in their favor, principally for Brady and Hope, who, among the public and other crooks alike, were widely perceived as celebrities for their daring exploits. But an escape plan was foiled, and on December 10, each man spent an hour in the stocks, followed by 40 lashes with a cat o’nine tails, leaving them subdued and bloodied. Their backs were then covered with grease and the men were taken to their cells. More than 500 citizens attended the gruesome “event.” Despite it all, admirers proclaimed that no jail could hold Brady and Hope and they would surely escape within 90 days.

Ample healing time was required, especially for the fair-skinned Brady, but by February 1874, they were all feeling healthy again. On the 24th of that month, just 76 days after the severe whipping, an escape plan concocted by Brady and Hope was brought to fruition.

At about 1 a.m., the night warden heard a noise and cracked the door open to investigate. He was immediately overpowered by a dozen men who tied, handcuffed, and gagged him. The prisoners were freed, after which two ladders were used to scale the wall and complete the breakout. A tugboat that had carried the men from Philadelphia was used to complete their escape to New York.

In the days that followed, spectacular headlines added further to their legend, and a manhunt was begun. For Jim Brady, it was his third escape in just over a year, but it hardly mattered. Rather than go into hiding, he continued “working” while carefully avoiding lawmen. Crime, after all, was his life and livelihood, and because of that, Big Jim Brady remained engaged.

There were strong suspicions that he assisted in two bank robberies in Wellsboro, Pennsylvania, in 1874 and 1875. In the latter year, he also led a team of burglars in a high-profile attack, robbing Arthur Heaney’s pawnshop in New York City. After resisting and suffering a terrible beating, Heaney identified Brady as the ringleader. More than ever the heat was on, but Jim managed to dodge his pursuers.

In 1875, he was linked to highly publicized bank-robbery attempts in Great Barrington, Massachusetts, and Barre, Vermont. Both efforts ultimately failed.

In early 1876, newspapers reported an unsuccessful assault on the bank in Northampton, Massachusetts, leaving the impenetrable vault badly damaged but intact. Almost a full day passed before an expert arrived from the company to open it and begin repairs. Officials were stunned to discover the awful truth: the door had been purposely resealed, and a robbery had indeed occurred after all. The take was enormous: more than $720,000 in cash and bonds had been stolen.

For more than a century, the Northampton heist was considered one of the greatest bank robberies in American history. The $720,000 value equals about $16 million in 2013. The Pinkerton archives include Jim Brady among the gang that pulled it off.

Several weeks after the robbery, he was one of two men who retrieved the loot, which had been hidden near the crime scene—in the walls and floor of a nearby schoolhouse. It was typical Brady: brash, daring, and using a hiding place devoid of suspicion. Bank cashier Whittelsey, whose family was tied up during the robbery, described the leader of the gang as “a large, powerful man, of perfect coolness and self-possession.” For experienced investigators, it was a by-the-book description of Albany Jim Brady.

Some of the Northampton robbers were eventually captured (two were sprung by Jim in a remarkably intricate escape plan), but Brady himself remained at large and unprosecuted.

Next week, Part 3: Big trouble for Big Jim.

Photos: New York Times, 1873; Philadelphia Enquirer, 1873; New York Times, 1873.