Barrington: Daring Killer Guns Down Two FBI Agents

Today’s post features the Battle of Barrington. This 1934 shootout between gangster Baby Face Nelson and two FBI agents left the two agents dead, but also ended Nelson’s career of crime. It further heralded the twilight of the so-called “Public Enemies” era.

In the American Midwest in the early 1930s, while the country suffered from the worst of the Great Depression, several infamous criminal gangs rose to prominence. Newspaper headlines and cinema newsreels regularly featured names like John Dillinger, Pretty Boy Floyd, Machine Gun Kelly, and Lester Joseph Gillis (a.k.a. George “Baby Face” Nelson). Local police and even the nascent FBI seemed unable to put a stop to these so-called “Public Enemies.” As 1934 approached its end, the Division of Investigation (rechristened the Federal Bureau of Investigation on March 22, 1935) began to gain the upper hand. Their victories were not without cost, however.

The Battle of Barrington: Background

The man at the center of the Battle of Barrington was Lester Gillis, better known by the alias George “Baby Face” Nelson. Nelson was a career criminal who seemed to take a psychotic pleasure in killing. He gained infamy for participating in multiple bank robberies and violent clashes with law enforcement throughout the Midwest. He was an associate of John Dillinger and other criminal figures from the “Public Enemies” era. Nelson had eluded capture for several months following Dillinger’s death in July 1934. Now, at the end of November 1934, his luck ran out.

Baby Face Nelson mugshot
Baby Face Nelson in a 1931 mugshot

The climactic clash between Nelson and the FBI occurred near the Chicago suburb of Barrington, Illinois, on November 27, 1934. What began as a quiet, cold Tuesday ended with two FBI agents dead and the notorious gangster fatally wounded. The running gunfight marked one of the most significant and violent encounters in the Bureau’s early history.

The Battle of Barrington Unfolds

Events that led to the gunfight began earlier in the day, when federal agents received information suggesting Nelson might be in the area northwest of Chicago. Two agents, Inspector Samuel Cowley and Special Agent Herman “Ed” Hollis, were among those assigned to track and apprehend him. That afternoon, they spotted Nelson driving with his wife, Helen Gillis, and associate John Paul Chase near the town of Fox River Grove. Federal agents began pursuit, initiating a series of events that quickly escalated into a running gun battle.

A recreation shows the positions of Nelson's and the federal agents' cars during the Battle of Barrington (Chicago Tribune)
A recreation shows the positions of Nelson’s and the federal agents’ cars during the Battle of Barrington (Chicago Tribune)

A brief car chase followed westward along U.S. Route 14 into Barrington. Heavily traveled today, at the time, it was a quiet rural road. Cowley and Hollis pursued Nelson in one car, while Agents Thomas McDade and William Ryan followed in another. The chase came to a halt near the entrance to North Side Park, a grassy expanse just outside of the downtown district. There, both parties stopped and exchanged gunfire again.

Special Agent Herman Edward "Ed" Hollis was mortally wounded during the Battle of Barrington (FBI)
Special Agent Herman Edward “Ed” Hollis was killed during the Battle of Barrington (FBI)

Nelson got out of his car with a .351 Winchester rifle, and Chase armed himself as well. Overmatched in firepower, Agents Hollis and Cowley nevertheless returned fire with their service weapons, ducking behind their vehicle. Witnesses later recalled the sounds of gunfire cracking through the otherwise still air, and the shouts of the combatants taking cover and issuing commands.

Inspector Samuel Parkinson Cowley was mortally wounded during the Battle of Barrington. He died at 2:00 a.m. the following day, but lived long enough to identify his attacker as Nelson. (FBI)
Inspector Samuel Parkinson Cowley was mortally wounded during the Battle of Barrington. He died at 2:00 a.m. the following day, but lived long enough to identify his attacker as Nelson. (FBI)

The Battle of Barrington Concludes

Nelson fought fiercely despite being outnumbered. He was hit multiple times early in the exchange but continued to attack. During the shootout, Agent Hollis was critically wounded. Cowley managed to maintain his position and continue firing until he, too, was mortally injured. Nelson, his severe wounds notwithstanding, approached the federal car and reportedly fired the fatal shots into Cowley before fleeing the scene with Chase and his wife.

Baby Face Nelson lies on the undertaker's slab in the Niles Center morgue (Chicago Tribune)
Baby Face Nelson lies dead on the undertaker’s slab in the Niles Center morgue (Chicago Tribune)

Chase helped Nelson back into their bullet-riddled car, and the three drove away, leaving behind the two stricken agents and a crime scene littered with spent cartridges. Witnesses provided conflicting accounts of the sequence of events, but the battle, which lasted several minutes, left an indelible mark on the local community.

Nelson died from his wounds later that night. His body was found wrapped in a blanket and left near a cemetery in the Chicago suburb of Niles Center (now Skokie). Helen Gillis later surrendered to authorities. Chase managed to evade capture for some time but was ultimately caught and arrested.

Aftermath of the Battle of Barrington

The deaths of Agents Cowley and Hollis shocked the Bureau. Both men were regarded as experienced and committed law enforcement officers. Their loss highlighted the dangers federal agents faced during an especially violent era in American criminal history. The Bureau began placing new emphasis on training, investigative rigor, and armed response. But the Battle of Barrington served as a reminder of the risks involved in confronting heavily armed fugitives.

The Chicago Tribune announces Nelson's death after the Battle of Barrington (Chicago Tribune)
The Chicago Tribune announces Nelson’s death after the Battle of Barrington (Chicago Tribune)

At the time, Barrington was a modest village of just over 2,000 people, unaccustomed to such violence. Residents gathered near the site in the hours and days following, observing the bullet holes in road signs and fences. Newspapers across the country picked up the story as well, further cementing the battle in the public’s mind.

Epilogue

Barrington marked the end of Nelson’s criminal career and was a turning point in the campaign against the era’s most notorious outlaws. Within a year, the so-called “Public Enemies” period would largely come to a close, as most high-profile figures were captured or killed.  Concurrently, the FBI’s authority continued to expand.

Nearly a century has passed since the Battle of Barrington, but it remains a notable chapter in the story of American law enforcement. A small plaque today marks the site of the shootout, honoring the memory of the two agents who lost their lives in the line of duty.

Plaque commemorating the Battle of Barrington (Author's photo)
Plaque commemorating the Battle of Barrington (Author’s photo)

Many authors have written about the events and players of the “Public Enemies” era. The absolute best, in my opinion, is Bryan Burrough’s Public Enemies: America’s Greatest Crime Wave and the Birth of the FBI, 1933-34. You can also check out Baby Face Nelson: Portrait of a Public Enemy by Steven Nickel. Another good read is John Toland’s The Dillinger Days. It is an older book, but it was one of the best early histories of Depression-era outlaws.

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Harry Pierpont: Life of a Daring Killer

Of all the historical crime topics, I find the so-called “Public Enemies” era of the 1930s the most fascinating. One of the key figures of that time was Harry Pierpont. Known to associates as “Pete” or “Handsome Harry,” Pierpont was a mentor and partner of famed bank robber John Dillinger. At least he was until lawmen nabbed the Dillinger gang while they vacationed in Arizona.

Harry Pierpont

Harry Pierpont was born in Muncie, Indiana, on October 13, 1902. A few years later, the family lived in Indianapolis. Harry was an intelligent child and did well in school. Census records in 1920 show him living with his family in Indianapolis. The census listed his occupation as a bench worker in an automobile plant (Indianapolis was home to many automobile-related industries in the early 1900s).

Harry Pierpont (weeklyview.net)
Harry Pierpont (weeklyview.net)

In the summer of 1921, Pierpont got caught in a belt-driven machine at the factory, which crushed his left arm. The arm never fully recovered. He also suffered a head injury in the same accident. His behavior changed after the head injury. He complained of headaches, dizziness, and vision problems and was prone to periods of sleepiness.

Harry Pierpont Gets in Trouble with the Law

On January 2, 1922, Pierpont stole a car and drove it to Greencastle, Indiana. There, he robbed the Cook Hardware Store. Included in his haul were nine guns.

Five days later, Pierpont tried to steal a car in Indianapolis. When the owners, Mr. and Mrs. Devine, accosted him, he fired a shot, slightly wounding Mr. Devine. Mrs. Devine was holding a roast and hit Pierpont over the head with it. Reports do not indicate whether or not the roast was frozen.

Harry Pierpont mugshot (Indiana State Archive)
Harry Pierpont mugshot (Indiana State Archive)

As a result of these two crimes, Pierpont arrived at the Indiana State Reformatory on March 12, 1922, for a two- to fourteen-year sentence. On November 17 of the following year, the state transferred him to the newly constructed reformatory at Pendleton, Indiana.

Hary Pierpont Continues Crime after Parole

After lobbying from his mother, Lena, the state parole board granted Pierpont parole on March 6, 1924. He lived in Brazil, Indiana, where his family had moved. However, he continued to associate with known felons.

In April 1925, police identified Harry Pierpont as the leader of a gang that had robbed several banks in Indiana. The gang consisted of seven members who identified Pierpont as their leader. The banks hit by the gang included the South Marion State Bank in Marion, the Citizens State Bank in Noblesville, and the Upland State Bank in Upland,

Police in Detroit arrested Pierpont and an accomplice, Thaddeus “Ted” Skeer, at their apartment hideout on April 2, 1925. While Pierpont and Skeer awaited trial in the Howard County jail in Kokomo, a Pinkerton detective discovered a cache of saw blades in their cells.

At his trial, Pierpont surprisingly admitted his guilt and was convicted. He received a sentence of ten to twenty-one years. He ended up back in the Pendleton Reformatory on May 6, 1925.

Harry Pierpont in Pendleton and Michigan City

It was in the Pendleton Reformatory that Pierpont met Homer Van Meter and a young John Dillinger. Dillinger had been sentenced to ten to twenty years for an ill-conceived attempt to rob a grocer in his hometown of Mooresville, Indiana.

Pierpont was anything but a model prisoner. His defiant behavior and multiple escape attempts prompted Warden A.F. Miles to transfer him to the Indiana State Prison in Michigan City on July 30, 1925. At Michigan City, Pierpont became the leader of a clique consisting of Charles Makley, Russell “Boobie” Clark, and John “Red” Hamilton. Dillinger and Van Meter joined the group after their transfers from the reformatory to the prison.

Mugshots of Charles Makley (L), Russel Clark (C), and John Hamilton (R)
Mugshots of Charles Makley (L), Russel Clark (C), and John Hamilton (R)

Harry Pierpont Engineers a Prison Break

During the summer of 1932, Pierpont began planning a massive prison break. He included Makley, Hamilton, and Clark in his plans. Pierpont also invited Dillinger to help from the outside (he expected to be paroled soon). His reward would be inclusion in the convicts’ bank-robbing gang.

In the meantime, Walter Dietrich joined Pierpont’s coffee klatch and began instructing the members on the techniques of the remarkable bank robber, Herman “Baron” Lamm.

By the spring of 1933, they were ready. As expected, Dillinger received his parole on May 10, 1933. He made nominal motions of “going straight” but soon began robbing grocery stores and banks to raise cash for the breakout. He acquired three .45 caliber handguns and managed to smuggle them into the prison.

Harry Pierpont's star pupil, John Dillinger (FBI Mugshot)
Harry Pierpont’s star pupil, John Dillinger (FBI Mugshot)

Shortly after 2:00 on the afternoon of September 26, 1933, Pierpont and his co-conspirators put their plan into action. Using the guns Dillinger provided, they, along with several other prisoners, took guards hostage and proceeded to move toward the prison’s exit. Using threats, they got through the three steel doors and found themselves in the prison’s administration building, where they took Warden Louis E. Kunkel hostage as well. Some escapees traveled to a hideout in Hamilton, Ohio, while others laid low at a farm Pierpont’s parents owned near Leipsic, Ohio.

Harry Pierpont Rescues Dillinger

Meanwhile, Dillinger had been arrested for a bank robbery in Bluffton, Ohio, and was being held in the Allen County Jail in Lima. Pierpont decided to rescue him.

On October 12, 1933, Pierpont, Makley, and Clark entered the jail at about 6:25 p.m. They told Sheriff Jess Sarber that they were officials from Indiana there to return Dillinger to that state. When Sarber asked for their credentials, Pierpont shot twice, hitting the sheriff once in the abdomen.

Allen County, Ohio, Sheriff Jess Sarber (FOP Ohio)
Allen County, Ohio, Sheriff Jess Sarber (FOP Ohio)

When Sarber refused to turn over the keys to Dillinger’s cell, Makley and Clark beat him. Sarber’s wife dug the keys out of a drawer to stop the assault. With Dillinger now free, the gang locked Mrs. Sarber and a deputy in a cell and made their escape.

Sheriff Jess Sarber died about ninety minutes later.

Harry Pierpont and the Dillinger “Terror Gang”

The gang now embarked on an audacious robbery spree. They started by raiding police stations in Auburn and Peru, Indiana, scoring many guns and bulletproof vests.

Next on the agenda were banks. The gang quickly raided the Central National Bank in Greencastle, Indiana, on October 23. On November 20, they hit the American Bank & Trust Company in Racine, Wisconsin.

After two successful scores, the gang decided on a Florida vacation. Renting a beach house in Daytona, the trip’s highlight was a New Year’s Eve barbecue, with Dillinger emptying his machine gun at the moon at midnight.

After Daytona, the gang hit the First National Bank in East Chicago, Indiana, on January 15, 1934. While Dillinger and Hamilton were inside the bank, East Chicago police took up positions outside. As Dillinger exited the bank, Officer William P. O’Malley took a shot at him. Dillinger, wearing a bulletproof vest, was uninjured but returned fire, killing O’Malley. The other officers opened fire, wounding Hamilton.

Pierpont’s Flight and Capture

The gang decided to take a trip out west to escape the heat in Indiana. Pierpont, Dillinger, Makley, and Clark ended up in Tucson, Arizona. The gangsters stood out in what was still an Old West town with hitching posts on the streets. Locals soon recognized them, and law officers arrested them one by one on January 25.

Harry Pierpont being interrogated in a Tucson, Arizona, jail cell
Harry Pierpont being interrogated in a Tucson, Arizona, jail cell

Dillinger was extradited to Indiana to face trial for Officer O’Malley’s murder. Ohio took Pierpont, Makley, and Clark for the murder of Sheriff Sarber.

In March 1934, Pierpong, Makley, and Clark were convicted of Sarber’s murder. Testimony from Ed Shouse, a former gang member, helped seal their fate. Pierpont and Makley were sentenced to death, while Clark received a life sentence.

Epilogue

With time running out, Pierpont and Makley made a desperate attempt to escape the Ohio Penittentary’s death house on September 22, 1934. Brandishing fake pistols carved from soap and covered with shoe polish, they got out of their cells but met guards armed with rifles at the death house door. The guards opened fire, killing Makley and severely wounding Pierpont.

Pierpont went to his death on October 17, 1934. Still suffering from the wounds he suffered a month earlier, guards carried him to the electric chair.

You can read more about Pierpont, Dillinger, and the rest of the gang in Bryan Borough’s excellent history of the 1930s gangsters, Public Enemies. Other books are John Toland’s The Dillinger Days and Dillinger: The Untold Story by Russell Girardin.

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Ma Barker: Expert Criminal or Feeble Old Woman?

This week’s blog post concerns one of my favorite subjects: the Public Enemies era of the early to mid-1930s. You may have heard of my subject before. Her name was Arizona Donnie Clark Barker. She went by Kate, but history remembers her as the infamous Ma Barker. She had a reputation as a bandit queen who masterminded her sons’ numerous criminal activities. J. Edgar Hoover referred to her as “the most vicious, dangerous, and resourceful criminal brain of the last decade.” But was that the real Ma Barker?

Ma Barker in the Early Years

Ma Barker was born in Ash Grove, Missouri, on October 8, 1873. Ash Grove is in southwestern Missouri, about sixty miles from Joplin and close to Missouri’s borders with Arkansas and Oklahoma. A rumor claimed she saw Jesse James and his gang ride through town as a girl, and this experience sparked a thirst for adventure.

Probably the best-known photo of Ma Barker
Probably the best-known photo of Ma Barker

Whether the bit about Jesse James was fact or legend, “Arrie” Clark didn’t have much adventure in her life. At least not at first. In 1892, she married a tenant farmer named George Barker, a man the FBI described as “shiftless.” Together they had four sons. Neither George nor Arrie paid much attention to their sons’ educations, and all four were, according to the FBI, “more or less illiterate.” But as her boys turned to crime, Arrie would do everything she could to get them off, regardless of what they’d done.

Ma Barker points to an outdoor Christmas tree. Apparently, this was a "thing" in the Ozarks at the time.
Ma Barker points to an outdoor Christmas tree. Apparently, this was a “thing” in the Ozarks at the time.

By 1931, George was gone. Either he left, or Arrie threw him out. It’s not clear which. Arrie herself was living in dire poverty in a dirt-floor shack. By this time, she’d taken up with a jobless man named Arthur “Old Man” Dunlop. But in 1931, things improved, in a manner of speaking, when her son Fred got out of jail and formed the Barker-Karpis gang with prison friend Alvin Karpis. (Side note: the gang took Dunlop for the proverbial “one-way ride” when they thought, incorrectly, that he had ratted them out to police in St. Paul, Minnesota.)

Ma Barker with Arthu "Old Man" Dunlop
Ma Barker with Arthu “Old Man” Dunlop

Ma Barker and the Outlaw Life

Arthur Barker, nicknamed “Dock” and recently released from prison, joined his brother and Karpis in 1932. At first, they robbed banks, but after moving to the infamously corrupt city of St. Paul, Minnesota, they committed two high-profile kidnappings for ransom. In the first, they snatched brewery president William Hamm and got his family to pay a $100,000 ransom. For their encore, they kidnapped banker Edward Bremer and successfully obtained $200,000.

The Bremer caper proved to be the gang’s undoing. FBI agents identified one of Dock’s fingerprints on a gas can the kidnappers left behind near Portage, Wisconsin. A year later, Karpis was the only gang member still free, and he didn’t remain free for long.

Life for the Barker-Karpis gang was one of constant movement. As law enforcement closed in, the gang had to find a new hideout, frequently with little or no warning. Ma Barker, now going by “Kate” instead of “Arrie,” moved along with her sons, Karpis, and their girlfriends. Kate was never too keen on any of the boys’ girlfriends, which sometimes led to considerable tension.

The house in Ocklawaha, Florida where FBI agents killed Freddy and "Ma" Barker. The arrow points to the bedroom where the bodies were found.
The house in Ocklawaha, Florida where FBI agents killed Freddy and “Ma” Barker. The arrow points to the bedroom where the bodies were found.

The End for Fred and Ma Barker

In January 1935, the FBI arrested Dock in Chicago. Searching his apartment, they found a map indicating the gang was lying low in a house near Ocklawaha, Florida. In the early morning hours of January 16, agents surrounded the house. Unknown to the G-Men, only Fred and his mother were inside. When agents demanded the gang’s surrender, Fred opened fire. The FBI returned fire, and guns blazed away for hours.

When gunfire from the house finally stopped, the FBI ordered a local handyman to enter the dwelling wearing a bulletproof vest. The handyman, Willie Woodbury, reported that no one was alive in the house. Fred’s body was riddled with bullets, but only one bullet appeared to have killed Kate. A machine gun lay between the two bodies.

The Legend of Ma Barker as a Criminal Mastermind

Horrified that his agents had killed an elderly woman with their indiscriminate gunfire, FBI director J. Edgar Hoover cranked the Bureau’s publicity machine into high gear. This was the genesis of the utterly bogus myth that Ma Barker had run a “crime school” for her sons when they were boys and planned their robberies. Hoover himself piled on with his fabrication about Ma Barker’s criminal brain.

Hoover’s claim was pure fiction. Bank robber Harvey Bailey, who knew the Barkers, wrote in his autobiography that Kate “couldn’t plan breakfast.” Alvin Karpis, the actual gang leader, described her as having a fondness for “hillbilly” music, jigsaw puzzles, and the radio show Amos ’n’ Andy. He further maintained:

The most ridiculous story in the annals of crime is that Ma Barker was the mastermind behind the Karpis-Barker gang…. She wasn’t a leader of criminals or even a criminal herself. There is not one police photograph of her or set of fingerprints taken while she was alive…she knew we were criminals, but her participation in our careers was limited to one function: when we traveled together, we moved as a mother and her sons. What could look more innocent?

A good story often subsumes the truth. So it was with Ma Barker. The FBI’s mythmaking set the stage. In films, a machine-gun-toting Lurene Tuttle in Ma Barker’s Killer Brood and a cigar-chomping, wisecracking Shelly Winters in Bloody Mama have continued to do Hoover’s work for him.

Epilogue

Dock Barker and Alvin Karpis wound up in Alcatraz Federal Penitentiary. On January 13, 1939, Barker attempted to escape under the cover of a foggy night along with inmates Dale Stamphill, Henri Young, William “Ty” Martin, and Rufus McCain. Guards spotted them and opened fire, fatally wounding Barker.

Karpis fared better. Paroled in 1969, he was deported to his native Canada. He moved to Spain in 1973 and died there on August 26, 1979.

Bryan Burrough’s excellent book Public Enemies is an entertaining look at Ma Barker, the Barker-Karpis Gang, and their criminal contemporaries.

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John Dillinger: A Famous Bandit’s Best Daring Escapes

Last week’s case covered Joseph Christopher. Between September and December 1980, eleven Black men and one boy died in Christopher’s racially motivated attacks. This week, I’m tackling one of my favorite subjects, the infamous depression-era gangster John Dillinger. Dillinger is perhaps America’s most famous bank robber. A proper telling of his saga would take more space than would fit in a single blog post. But he also possessed a talent for getting out of jails and tight spots. So, I will tell you about some of his spectacular escapes instead of the whole story.

The Advent of John Dillinger

The popular image of John Dillinger is a farm boy who became a criminal, but he grew up in the city. He was born in 1903 in Indianapolis, where his father (also John) owned a grocery store. Mollie Dillinger, his mother, passed away before Johnnie’s fourth birthday. Audrey Dillinger, his older sister, helped raise him until the elder Dillinger remarried in 1912. Young John showed a rebellious streak, so John senior decided to move to the rural community of Mooresville, southwest of Indianapolis.

John Dillinger as a young man
John Dillinger as a young man

One of Dillinger’s new pals in Mooresville was an ex-con named Ed Singleton. Together, the two planned to rob Frank Morgan, a local grocer, on Saturday, September 6, 1924. Writer Brian Burrough described the caper as “fueled by stupidity and alcohol,” and both men soon found themselves in jail. Following his father’s advice and the prosecutor’s suggestion, Dillinger entered a guilty plea, expecting leniency. He drew an eye-popping sentence of ten to twenty years instead. His partner hired a lawyer, pleaded not guilty, and served only two years.

John Dillinger mugshot (FBI)
John Dillinger mugshot (FBI)

Dillinger spent nine and a half years incarcerated, many of them in the Indiana State Penitentiary in Michigan City. His prison pals all happened to be hardened career criminals, and he learned a lot at the feet of these masters. Indiana paroled Dillinger in 1933, and he started forging his path as a bank robber.

John Dillinger at the Indiana State Penitentiary

Dillinger didn’t break out of the Penitentiary himself; he orchestrated the escape of the friends he left behind after his parole. Using stolen money, he procured guns and somehow got them into the hands of his convict buddies. On September 26, 1934, ten inmates used them to overpower guards and run. The escapees included Harry “Pete” Pierpont, Charles Makley, John “Red” Hamilton, and Russell “Boobie” Clark. All later became core members of the Dillinger gang.

Entrance to the grim Indiana State Penitentiary in Michigan City, Indiana
Entrance to the grim Indiana State Penitentiary in Michigan City, Indiana

Dillinger, however, landed back in jail. Police in Dayton, Ohio, arrested him at a girlfriend’s apartment for robbing a bank in nearby Bluffton. They lodged him in the Allen County Jail in Lima. While his friends enjoyed their newfound freedom, Dillinger appeared to be on his way back to prison.

Allen County, Ohio Jail

Allen County Sheriff Jess Sarber ran the county jail. Kind, roly-poly, and competent, Sarber nevertheless had no previous law enforcement experience. He sold used cars before the Depression forced him out of business.

Allen County, Ohio sheriff Jess Sarber
Allen County, Ohio sheriff Jess Sarber

On Thursday, October 12, Dillinger played pinochle in the jail’s bullpen while Sheriff Sarber read the newspaper. At 6:25 in the evening, the jail’s outer door opened. Three men in suits announced they had come to extradite Dillinger to Indiana. Sarber asked for their credentials, and the first man, Pierpont, shot him in the chest. Dillinger escaped, but Sheriff Sarber died, a murder that would return to haunt Pierpont, Makley, and Clark.

Office of Dr. Charles Eye

By now, Dillinger was a bank robber with a reputation and a pack of lawmen on his trail. Based on a tip, Chicago police planned a raid at the office of dermatologist Dr. Charles Eye. At 7:25 p.m. on November 14, Dillinger drove up in his Essex Terraplane with his girlfriend, Billie Frechette, in the passenger seat.

Emerging from Dr. Eye’s office, Dillinger spotted several cars parked heading the wrong way. Telling Billie to hold on, he slammed the car into reverse and backed into busy Irving Park Boulevard. A short chase followed, but Dillinger eluded his pursuers.

John Dillinger’s Famous Escape at Crown Point

After spending Christmas 1933 in Florida, Dillinger’s gang headed west to Tucson, Arizona. Clark and Makley booked into the Hotel Congress downtown. Things went well until a fire in the hotel led suspicious firefighters to tip off the police. The entire gang soon found themselves under arrest.

Dillinger at the Lake County jail in Crown Point, Indiana. Sheriff Lillian Holley is at left. In the center, is prosecutor Robert Estill, who hoped to send Dillinger to Indiana's electric chair. This photo of Estill cozying up to the famous gangster derailed his ambition to become Indiana governor (Getty Images)
Dillinger at the Lake County jail in Crown Point, Indiana. Sheriff Lillian Holley is at left. In the center, is prosecutor Robert Estill, who hoped to send Dillinger to Indiana’s electric chair. This photo of Estill cozying up to the famous gangster derailed his ambition to become Indiana governor (Getty Images)

Makley, Clark, and Pierpont went to Ohio to stand trial for the murder of Sheriff Sarber in Lima. Dillinger went to the Lake County Jail in Crown Point, Indiana. There he faced a murder charge related to the death of a policeman killed during a robbery in East Chicago. Lake County Sheriff Lillian Holley claimed her jail was “escape proof.” It wasn’t. Dillinger escaped using a pistol he managed to acquire. He claimed he used a fake gun made of wood; jailers contended it was real. Whatever the truth, Dillinger bolted.

The Lake County jail in Crown Point, Indiana, immediately after Dillinger's escape. The building at left is the courthouse. A walkway between buildings is visible in the center of the picture (Chicago Tribune)
The Lake County jail in Crown Point, Indiana, immediately after Dillinger’s escape. The building at left is the courthouse. A walkway between buildings is visible in the center of the picture (Chicago Tribune)

Lincoln Court Apartments

In March 1934, Dillinger and Billie, posing as Mr. and Mrs. Carl Hellman, moved into Apartment 303 of the Lincoln Court Apartments in St. Paul, Minnesota. Soon after the pair moved in, the suspicious landlady tipped off the Bureau of Investigation (precursor to the FBI). Two agents staked out the apartment. On March 31, they recognized and traded shots with Dillinger associate Homer Van Meter.

The Lincoln Court Apartments in 2016 (Author's Photo)
The Lincoln Court Apartments in 2016 (Author’s Photo)

Hearing the shooting, Dillinger let loose a machine gun volley through the door and ran down the stairs and out the back door. One of the agents’ bullets hit him in the left calf, but Dillinger escaped again.

John Dillinger and the Battle of Little Bohemia

Dillinger and his new gang planned a quiet weekend holiday for April 20-22, 1934. They chose a remote lodge in the North Woods of Wisconsin called Little Bohemia. On Sunday morning, the nervous owner’s wife smuggled a message to the BI field office in Chicago. By evening, a posse of federal agents led by Hugh Clegg and Melvin Purvis gathered outside the lodge.

Three men came out of the lodge while agents prepared their raid. The men got into a car and started to drive off. Agents shouted for them to stop, but the car’s radio drowned out the order. The assembled lawmen opened fire, killing one of the men and wounding the others. The men all worked at a nearby Civilian Conservation Corps camp. None knew John Dillinger.

Little Bohemia Lodge after the Bureau of Investigation raid (Wikimedia Commons)
Little Bohemia Lodge after the Bureau of Investigation raid (Wikimedia Commons)

The gunfire alerted the gangsters, and they fanned out from Little Bohemia. Dillinger fled from Little Bohemia’s unguarded back side, hidden by a ridge separating the lodge from Little Star Lake.

FBI mugshot of John Dillinger (FBI)
FBI mugshot of John Dillinger (FBI)

During his getaway, Lester “Baby Face Nelson” Gillis shot and killed BI agent W. Carter Baum and wounded another agent and a local officer.

Epilogue

Dillinger’s luck finally ran out on the night of July 22, 1934. Dillinger and two women went to the movies. The three picked the Biograph Theatre on Lincoln Avenue, showing Manhattan Melodrama starring Clark Gable. Tipped off by one of his companions, the so-called “Woman in Red,” BI agents and East Chicago police gunned down the outlaw as he exited the theater.

A crowd gathers outside Chicago's Biograph Theatre after Bureau of Investigation agents killed John Dillinger in what amounted to an assassination
A crowd gathers outside Chicago’s Biograph Theatre after Bureau of Investigation agents killed John Dillinger in what amounted to an assassination

Several excellent books chronicle the John Dillinger story. The best is Public Enemies by Bryan Burrough. The Dillinger Days by John Toland and Dillinger: The Untold Story by Russell Girardin and William J. Helmer are also excellent.

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