John Dillinger

Between July 4, when Dillinger left the Probasco home, and the night of the shooting outside the Biograph, there are several variations of Dillingers movements. One of the conflicts that has never been resolved was whether or not Dillinger knew Anna Sage prior to June/July 1934. Therefore creating a second conflict did Sage introduce Dillinger to his new girlfriend, Polly Hamilton, a part-time waitress and full time prostitute whose work for Sage went back at least ten years, or did Hamilton introduce Dillinger to Sage?

Girardin claims that on July 4 Dillinger moved into Sages North Halsted Street apartment lock, stock and arsenal. The writer also claims that Polly Hamilton was living there too, although other historians say she maintained a suite at the Malden Hotel, some distance from the Sage apartment and near her waitressing job.

Dillinger spent the next couple of weeks in the company of the two women and with Sages son Steve, now in his early twenties. Dillinger was also maintaining contact with OLeary.

A Chicago Cubs' baseball game in
the mid 1930's (AP)

Van Meter went back to the home in Calumet City where he was sharing with Marie Comforti. The two couples took in the Worlds Fair one night and Dillinger continued to attend Cubs baseball games. Dillinger and Van Meter had washed their hands of Baby Face Nelson after the South Bend robbery. They were now making plans together for one last score. Girardin relates the conversation between Dillinger and OLeary:

Ill let you in on something, Art. Van and I are going to pull off the biggest job of our lives. It will be one of the biggest jobs in the world. Just me and Van were not cutting anybody else in on this. Ill tell you what it is were going to take a mail train. Weve got it spotted, weve been watching it for weeks, we know all its stops. We need the soup (nitro glycerin) to blow the door of the mail car. We also know how much money it will be carrying, and its plenty. Well have enough to last us the rest of our lives, and right after its over were lamming it out of the country.

The great train robbery Dillinger style was scheduled to take place the week after the Biograph shooting.

On Tuesday, July 17 OLeary visited James Probascos home to deliver the final payments Dillinger owed him. OLeary was floored by what Probasco told him. According to Probasco, Louis Piquette had told him that he was tired of being mixed up with a guy as hot as Dillinger. Piquette suggested that the two of them should clean ourselves and make a deal with the G to put Johnnie on the spot. What concerned OLeary was Probascos contention that part of the plot included killing OLeary to take the heat off Piquette.

OLeary had mixed feelings as he mulled over the things Probasco had told him. Mostly he dismissed them, thinking Probasco had blamed Piquette for Dillingers sudden departure from his home thus losing his $35 daily stipend. Still, the two men had known each other for 20 years. Later that day Dillinger met with OLeary and he was not in a good mood. Somehow Probasco had passed the same message to the outlaw.

Several things had happened recently to make Dillinger have second thoughts regarding his attorney. Piquette had approached Dillinger about providing the authorities with the information on Red Hamiltons demise so the lawyer could negotiate a reward for himself. Then there was the money given to Piquette for Pierpont and his family that never made it to them. In addition, Dillinger claimed Piquette had been talking too much about surrender.

OLeary relayed the following conversation to Girardin:

Art, I want you to get out of town, Dillinger said. Take your family, and go up to the north woods or some place.

What do you think youre going to do? asked OLeary.

Im going up to Piquettes office and leave him my card, replied Dillinger.

Dillinger handed OLeary $500 and the private investigator said good-bye for the last time, and left Chicago that night. OLeary later claimed he thought the whole episode was a fabrication by Probasco. It was never revealed whether he related any of this to Piquette before he left town.

Three days later, Friday, July 19, Piquette left Chicago to visit family in Platteville, Wisconsin. He claims the following day he received a telephone call from Dillinger. According to Girardin:

The outlaw declared that he had reconsidered the matter of surrender, and made an appointment to discuss it further with Piquette on Monday, July 23. Perhaps he was sincere and really desired to end his hunted-animal existence, or perhaps he planned to carry out his threat.

The conversation between Dillinger and Piquette was not the only call burning up the telephone lines on July 21, 1934.