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The Dillinger Gang Officially Rides

Updated on March 5, 2013
Harry Pierpont
Harry Pierpont | Source

Lead On, Dillinger

When the first newspaper story named Dillinger as the leader of the gang, Pierpont could care less. Dillinger, on the other hand, read every story with rapture, saved the stories, and he became more conservative in both manner and dress. They all lived quietly in expensive neighborhoods, rarely drinking, and if they did, it was only beer. Pierpont’s standard was to prepare for and commit crimes while sober. The men would all sit in the living or dining rooms and discuss things, just like any normal businessmen. Pierpont usually chaired the meetings, but everyone had a chance to speak his mind.

Greencastle Bank
Greencastle Bank | Source

Greencastle Central National Bank Robbery

For the first time after the Peru Police Department incident, the boys were discussing final plans for their first major robbery, which would be the Greencastle Central National Bank in Greencastle, Indiana. Pierpont knew the roads, as he once worked in the area, sketched the interior, and showed the escape routes.. Makley heard that merchants did a fabulous weekend business with home-coming at De Pauw University. The plan was to hit the bank on Monday, October 23, 1933.

At 2:45 in the afternoon, they parked the Studebaker next to the bank. Dillinger and his men walked to the bank. Hamilton stayed outside as the lookout, and the three others walked in. The guard had just gone to the basement to tend the fire. Pierpont headed for a cage to change a bill, then Dillinger pulled a gun and hopped over the counter, walking into the teller’s cage. The men were cleaning out the cash from the cages and vault. No shots were fired, and the gang walked out with over $74,000 in cash and bonds.

A short time later, the International News Service in Indianapolis scooped the robbery. The Bureau Chief, Jack Cejnar, took the call. He was informed by a Mr. King from American Surety Insurance, the claims adjuster, who he worked a deal with. Most of the policies that covered these banks said that they had to notify the insurance company before anyone else, so that gave Cejnar the edge on a good relationship.

4310 N. Clarendon Ave.
4310 N. Clarendon Ave. | Source

4310 Clarendon and the Stoolies

The gang was now back in Chicago. Dillinger, Pierpont, Mary Kinder, and Billie Frechette were sharing living quarters. Their residence was located at 4310 Clarendon. The bellboy handled most of their bags, but Dillinger and Pierpont carried their own suitcases, which of course, contained weapons and ammo.

The gang moved about Chicago quite a bit, no point in hiding in their apartments. They were wealthy citizens, and needed to behave as such. Dillinger even would look for police and photograph them. A week after the Greencastle robbery, he even called Captain Leach to ask “the stuttering bastard how he was.” Leach never took any of these calls as they were meant, to taunt him. His game was to trick his enemy into revealing something that would bite him later. He even had a couple of stoolies that infiltrated the gang, known as Art and Whitey. Art knew Dillinger in prison, and ran a few errands for him. Whitey worked for Lt. John Howe, who ran Chicago’s Scotland Yard Squad. Howe told Whitey that he was tired of putting him up at the LaSalle Hotel and wanted results. He promised Howe that he’d get Pierpont and Dillinger to a parking lot at 220 North State St. that night. Whitey managed to get Dillinger to come with him, but Howe and a friend, an Indiana officer thought that it would be better to wait until they could have the both of them.

Dr. Eye's Office
Dr. Eye's Office | Source

The Ambush

Next, it was learned from Whitey that Dillinger had an appointment with a Dr. Eye on Irving Park Blvd. on November 15. Art even confirmed the information according to Howe. Even though Pierpont wouldn’t be there, the lawmen thought that it was best to strike while they had the chance.

Dillinger would have a Terraplane with Illinois registration 1-269-037 and had an appointment at 7 p.m. The plan was that when Dillinger walked out of the building after the appointment, Leach’s lieutenant would just kill him, like it was a gangland murder. The lieutenant had second thoughts, and passed the job to Sgt. Art Keller, another of Leach’s men. Then another idea was planned—police cars would hem Dillinger in once he got in he Terraplane and gun him down. A carload of Indiana police met three Chicago detective squads, and everyone was assigned a position. Then they went to Irving Park Blvd.

There was the Terraplane, with Billie Frechette in the front seat. Dillinger exited the building, saw all the unmarked cars parked in the wrong direction, and naturally, became suspicious. He casually slid behind the wheel and told Billie to hang on. A shot was fired at Dillinger, which hit the doorpost, inches from his head. Dillinger floor it, and made a quick left.

Keller now used a shotgun. A patrol officer on his beat fired, as he wasn’t aware of the plan to capture Dillinger. The bullet hit Keller’s windshield, showering him with glass. The two cars raced for several miles. Then the Terralane approached a trolley crossing, where two trolleys were converging from opposite directions. Dillinger floored it, barely squeezing between the two trolleys. Artery had to swing around one of the trolleys, and eventually they were both on a dead end. The Terraplane quickly turned into a court, but Artery was going too fast, and went past. By the time he got turned around, the Terraplane was gone.

Shouse is a Dirty Rat

Dillinger went right to the apartment, told the rest of the gang about the ambush. They packed up and moved to Clark and Makley’s apartment. The next day, they decided that they were going to rob a bank in Racine, Wisconsin on November 20. While changing a large bill at the American Bank and Trust Company, Mary scoped out the bank. Then they drove around looking for the best getaway route. At their next meeting, they discussed getting rid of Harry Copeland, who was drinking to excess, and picked Shouse as the getaway driver.

What they didn’t know was that Shouse was planning to rob a bank on his own. While Dillinger and Pierpont were out buying a car the next day, Mary Kinder overheard Shouse trying to convince Hamilton to join him. Mary let Shouse know in no uncertain terms that she heard this deception. That evening, the gang voted to disband Shouse. When he appeared the next day, they tossed a wad of cash at him, told him to leave, and he took Clark’s car to California.

American Bank and Trust and Venetian Theatre
American Bank and Trust and Venetian Theatre | Source

American Bank and Trust Robbery

At 2:30 in the afternoon of the robbery, two city detectives parked on the side of the bank, letting out an employee of a Milwaukee newspaper who wanted to make a deposit, and then went to the pool room on the square.

Pierpont entered the bank with a roll of paper under his arm. He put up a Red Cross poster, almost completely blocking the view of the teller’s cages from the street. Now in came Makley, followed by Dillinger, and Hamilton. Makley went to Harold Graham’s cage, and told him it was a stick-up. Graham thought ti was a joke, and told him to go to the next window. Makley fired a shot, which went through Graham’s right elbow, into his right hip. As he fell, he hit the silent alarm button, which went right to the police station.

Employees and customers were dropping to the floor, as instructed. The President, cashier, and his assistant headed for the main vault. Dillinger ordered the President to open the vault. Pierpont prodded the cashier with his machine gun, as the President said that it was a double combination. The assistant ran to the rear door and saw the getaway car with Clark in it, parked in the area reserved for bank officials.

The alarm brought Sgt. Wilbur Hansen and Officer Cyril Boyard, who thought that it was the usual false alarm. The saw the detective’s car parked next to the bank, thinking that they beat them there. Boyard walked to the bank first and heard someone say to stick ‘em up. Pierpont tried to grab Boyard’s pistol from his holster, but the holster was too new, as it was too tight. Sgt. Hansen’s machine gun was pointed down, and Makley fired at him. Makley unbuckled Boyard’s Sam Browne belt, and yanked the holster off, as the gun wouldn’t come out for him, either.

Dillinger had cleaned out the vault and Hamilton had all the cash from the cages. Dillinger and Pierpont rounded up hostages—three female employees, President Grover Weyland, Officer Boyland, and an off-duty police officer. As they were marched outside, one of the girls disappeared into the large crowd that had gathered. The two detectives came running toward them from the pool hall, and Makley fired a burst from his machine gun. The bullets shattered the glass of the Wylie Hat Shop where one detective had ducked.. The second detective ran into the Venetian Theatre where he called headquarters.

President Grover Weyland
President Grover Weyland | Source

What Happened to the Hostages?

Pierpont had Weyland and Mrs. Patzke step on the left running board of their car, a large black Buick, while Boyard got on the right running board. Dillinger backed out, and a police car appeared from the opposite direction. A machine gun was raised, and Weyland waved madly. Eventually, Mrs. Patzke felt a car brush up against her during the getaway. Boyard got ordered off the car, and Mrs. Patzke and Weyland were pulled into the car. She was put in the back seat between Hamilton and Pierpont, while Weyland sat on the left jump seat.

Finally Dillinger stopped, and Clark changed license plates. Pierpont dumped the money from the white sack into a suitcase, and noticed a lot of ones.

Mrs. Patzke and Weyland were let out of the car somewhere near a clump of woods, and Pierpont tied their hands together loosely with shoe laces.

Matt Leach's Mess

Matt Leach got a lead in Indianapolis that Pierpont’s mother and brother would be driving through Terre Haute in a new Auburn. He passed this on to the local sheriff and Police Chief, and told them not to arrest them. He was thinking that if they were followed, they might lead the police right to the gang. It should come as no surprise, but Mrs. PIerpont and Fred were arrested. When Leach heard about this fiasco, he and Harvey Hire headed for Terre Haute. When Leach approached Lena Pierpont’s cell, she began insulting him, assuming that he had caused her incarceration. He then told the Chief of Police that they might as well release the two.

When Harry Pierpont heard about this embarrassment, he drove to Indianapolis, and when Leach walked out of his office with Harvey Hire, Pierpont drew a bead on Leach. When Hire unknowingly got in the way, Pierpont lowered his gun. It must have been Leach’s lucky day.

The Scotland Yard Squad and The Dillinger Squad

In Chicago, Lt. Howe of the Scotland Yard Squad got a tip that an Auburn that belonged to the Dillinger gang was being repaired at a Broadway garage and that was turned over to the city detectives. When John Hamilton and his new girl, Elaine Dent, walked into the garage that afternoon, Sgt. William Shanley was waiting. Hamilton fired first, left Shanley mortally wounded and fled the scene. Ms. Dent was captured, and went through her own theatrics for the police. Shanley died in Edgewater Hospital, once a winner of the Chicago Tribune Hero Award.

Two days after the death of one of Chicago’s Finest, Capt. John Stege was ordered to set up a special squad of forth chosen men. Stege ordered his men to shoot to kill. The Dillinger/Pierpont Gang’s headquarters at 2259 South Damen Avenue was filled with rifles, machine guns, bulletproof vets, tear gas guns, and almost worthless forty-pound steel shields.

The Dillinger Squad was on duty 24/7, divided into two watches. Sgt. Frank Reynolds had the night shift. He had already killed twelve dangerous criminals and was anxious to dispatch number thirteen, and danger was his middle name.

Billie Frechette and John Dillinger
Billie Frechette and John Dillinger | Source
George "Baby Face" Nelson
George "Baby Face" Nelson | Source

Getting Out of Town For a While

Hamilton’s close call brought hair-dyeing to the gang’s repoirtoire. Dillinger dyed his hair red, Pierpont, Hamilton, and Clark had acquired dark hair, and Dillinger began sporting a mustache to hide a scar that resembled a harelip.

Dillinger and Billie Frechette went to Wisconsin for a while, Pierpont, Mary Kinder, a new arrival, George Nelson, went on a trip down south. By the time they hit Tennessee, Baby Face Nelson, became too obnoxious, and the trip was called off. When they returned, everyone was looked for Johnnie, so the entire gang went to see Florida. Before they left for Daytona Beach Dillinger couldn’t resist and called Matt Leach and Sgt. Reynolds, just to antagonize them a little.

Dillinger and Bllie Frechette arrived in Daytona Beach two days before Christmas 1933. Clark and Makley were already at the beach house with their girls, and Hamilton came alone. On Christmas Eve, Dillinger and Billy Frechette had an argument, and Dillinger blackened both her eyes, over Shouse, who she had managed to get together with once. Pierpont and Mary Kinder found her with a bruised face and swollen eyes. Dillinger sent her back home with $1,000 and his new Ford.

Clark’s girlfriend, Opal “Mack Truck” Long insisted upon cooking the entire Christmas dinner. Later that day, when Mary and Silent Margaret looked out the door and saw high tide, they thought that it was a flood, and said so.


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    • aviannovice profile imageAUTHOR

      Deb Hirt 

      7 years ago from Stillwater, OK

      This is an older post,with several segments, too. If you like this one, you can check out the CLyde Barrow and Bonnie Parker series...

    • Mel Carriere profile image

      Mel Carriere 

      7 years ago from Snowbound and down in Northern Colorado

      Fascinating story about a fascinating subject. There are a lot of conspiracy theories about Dillinger, such as that he was actually robbing banks to fight the Illuminati. Are you branching outward from your bird posts, or is this an older hub that I just stumbled upon? Great read!

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      7 years ago from Stillwater, OK

      Hey, Rolly! I have seen pictures of The Congress. It is quite the place, even today.

    • Rolly A Chabot profile image

      Rolly A Chabot 

      7 years ago from Alberta Canada

      Hi Deb... great story of the Dillinger Gang, you have put a great deal of effort into this and congrates. Last year I was in Tucson and visited the Congress Hotel where they had stayed the last day.

      Hugs and blessings from Canada

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      8 years ago from Stillwater, OK

      Thanks, KoffeeKlatch! I know that it is lengthy, but there is a lot of info on the gang.

    • KoffeeKlatch Gals profile image

      Susan Hazelton 

      8 years ago from Sunny Florida

      Love this series. I'm working my way faithfully through it. I can't wait to read the nest installment. Up and awesome.

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      8 years ago from Stillwater, OK

      I'll bet she has seen a bit of memorabilia, Chris.

    • cam8510 profile image

      Chris Mills 

      8 years ago from Traverse City, MI

      My mother lives in Wabash, Indiana which is 16 miles from Peru.

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      8 years ago from Stillwater, OK

      It is in Hammond, IN, and also includes other '30s era gangsters. I'd love to see it one day.

    • cam8510 profile image

      Chris Mills 

      8 years ago from Traverse City, MI

      I have not been there. Where is it located?

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      8 years ago from Stillwater, OK

      Hey, Chris, thanks for the kudos. Have you been to the Dillinger Museum?

    • cam8510 profile image

      Chris Mills 

      8 years ago from Traverse City, MI

      Great job, Deb. I am enjoying this, partly because I grew up in Indiana. I just never really paid attention to the tales of this gang before. Thanks for the entertainment and education.

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      8 years ago from Stillwater, OK

      Yes, Jim, the police finally had to learn that sharing information was for the good of the country. Everyone wanted to receive the limelight, which caused so many problems with crimes like these. Even after the advent of the teletype, it was still hard to hear about major crimes.

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      8 years ago from Stillwater, OK

      Hey, Lela! Thanks a lot for your comments. I feel so appreciated!

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      8 years ago from Stillwater, OK

      Thanks so much, Eddy. Between this story and my pictures I have been consumed for the past two days. Once this story is completely finished, I will get caught up on reading and commenting on everyone's stories.

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      8 years ago from Stillwater, OK

      Hey, Martin! You are so welcome, my friend. I'm glad that you're enjoying it.

    • aviannovice profile imageAUTHOR

      Deb Hirt 

      8 years ago from Stillwater, OK

      Hey, Billy! You won't have to wait long...working on another part now.

    • xstatic profile image

      Jim Higgins 

      8 years ago from Eugene, Oregon

      What a strange and bloody life these people lived. It sounds as if police training was really inadequate to deal with these hardened criminals in those days.

      Another great series!

    • CreatePerfection profile image


      8 years ago from Beautiful Colorado


      Your stories of this era are so much fun to read. I truly am amazed at how you make the characters come alive for the reader. Thanks for taking the time to do the research and to share the stories with the rest of us. You are a wonderful writer.



    • Eiddwen profile image


      8 years ago from Wales

      Absolutly brilliant Deb;what a talented writer you are.

      I vote up,across and share.

      Have a wonderful day.


    • Mhatter99 profile image

      Martin Kloess 

      8 years ago from San Francisco

      Once again thank you for the effort you put in to unfold this drama.

    • billybuc profile image

      Bill Holland 

      8 years ago from Olympia, WA

      Don't leave us hanging....what happens next????

      Good one Deb! I need another installment.


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