He disliked publicity, and was content to let others, especially Dillinger, take credit for the bold bank robberies committed after the Michigan City prison break.

[1] Harry Pierpont was the middle child with an older sister Fern (b. September 21, 1900),[2] who died of tuberculosis when he was a teenager, and a younger brother Fred (b. July 5, 1906).

[15] After his release, Pierpont worked in Brazil, Clay County, Indiana where, during his first stint in prison, his family had moved; his father operated a sand and gravel business for several months.

[20] According to newspaper accounts, the gang had evidently studied the situation, knew the surroundings, and carried out their job with clockwork precision and uncanny accuracy.

[21] Grant County Sheriff Bert Renbarger and his deputies stopped a Nash car matching the description at Sweetser, Indiana, but the occupants were found to be out of town businessmen.

[25] After getting all the money in sight, they quickly left the bank and hopped into a waiting automobile, in which the sixth bandit sat, and departed north out of Upland, where it was reported they turned west.

[25] The automobile used by the bandits of the Upland State Bank and the Lebanon hardware store was found abandoned in the mud at Kempton, Indiana on December 27, 1924.

Late Saturday evening, December 27, 1924, James Robbins, 22, of Lebanon, Indiana, was arrested by local police after being seen flashing a large amount of cash.

Robbins confessed that on December 22, they had robbed the Shelby hardware store in Lebanon, then proceeded to Upland in a Moon car that had been stolen from Indianapolis the evening before.

[26] Behrens later confessed to Sheriff Renbarger of Grant County to his involvement in the Upland robbery, and told where he had hidden part of the money in Monticello.

[27] Robbins and Behrens were arraigned December 30, 1924 in Grant County Circuit Court after 5 o'clock, where they entered guilty pleas, and were sentenced to ten to twenty years in the Indiana State Reformatory.

[28] Marion "Red" Smith pleaded guilty in Grant County Circuit Court on December 31, 1924, and was sentenced to ten to twenty-five years for automobile banditry.

[31] On the morning of November 26, four men, whom he knew from prison, picked him up in Kokomo and told him they were looking for some place to "stick up", but hadn't decided on a city.

[31] Frazer was taken to the courthouse, a warrant was sworn out, he pleaded guilty to auto banditry, and was given a sentence of between ten and twenty-five years at the Indiana Reformatory.

[32] When the bank treasurer, Frank Steelman, failed to open the safe, he was hit with the butt of a pistol and suffered a severe scalp injury.

Captain William Pappert of the Fort Wayne police department had reported that Skeer had been seen at the Brunner woman's home with a large sum of money.

Members of the gang reportedly threw wild parties in Kokomo and Anderson, Indiana, where they displayed large sums of money to their women and spent "like drunken sailors".

[52] While being held in the Howard County jail in Kokomo, an escape attempt by Harry and Skeer was thwarted with the discovery of ten saw blades in the cells.

[53] Pierpont's parents came to Kokomo from their home in Brazil, Indiana on Saturday, April 4, 1925[34] and arranged with the firm of Overman & Healy and Carl Bree to look after the interests of Harry when arraigned and to defend him in his upcoming trial.

[34][50] Prosecutor Miller expected the prisoners to be bound over to the Howard circuit court, bonds to be fixed and a hearing held before Judge John Marshall.

[50] Howard County Sheriff Joseph Lindley adamantly denied reports that Pierpont and Skeer would be spirited away to another jail for safekeeping,[50] presumably the Pendleton reformatory.

[34] On April 6, 1925, Louise Brunner of Fort Wayne, held as a material witness and girlfriend of Skeer, was released under bond and allowed to return to her mother.

[58] Pierpont headed a prison clique that included Russell Clark, Charles Makley, John "Red" Hamilton and Dillinger, after his July 1929 transfer.

Others involved in the scheme besides Burns and Pierpont were Albert Roseberg, James Jenkins, Dick Day, Howard Ware, Maurice Delature, Frank Badgley, Louis West, Wayne Williams, Willard Tex, Russell Clark, all of whom were serving long sentences for murder, bank robbery and other habitual offenses.

[64] Pierpont was aided on the outside by his girlfriend Mary Kinder, who agreed to help with the break-out if her brother, Earl Northern, was added to the list of escapees.

After two o'clock that afternoon, Pierpont and Russell Clark told shirt factory superintendent George H. Stevens that one of the officials needed to see him in the basement.

[80] The convicts were ready to begin taking banks on their own, only to discover that Dillinger had been arrested in Dayton, Ohio four days before the escape, and was being detained in the Allen County jail in Lima.

With the Indiana State Police after them, the gang hid out in Chicago, with Dillinger, Pierpont, Mary Kinder and Billie Frechette sharing a flat at 4310 Clarendon Avenue.

On November 16, one day after Dillinger and Frechette had escaped an attempted police ambush, the gang made the final details for the robbery of a bank in Racine, Wisconsin.

On September 22, 1934, exactly two months after Dillinger's death, Pierpont and Makley carved phony pistols out of soap cakes, and painted them black with shoe polish, and made their move.