Death Alley Showdown: The Bold Rise and Bloody Fall of the Dalton Gang

The Dalton Gang, also known as the Dalton Brothers, stands as one of the most infamous outlaw groups of the American Old West. Active primarily from 1890 to 1892, they specialized in train robberies and bank heists across regions including Kansas, Oklahoma Territory, Indian Territory, and parts of California. Their story is one of a family transitioning from law enforcement to lawlessness, culminating in a dramatic and deadly showdown that ended their reign.

The gang centered on several sons of Lewis Dalton and Adeline Younger (a relative of the Younger brothers who rode with Jesse James). The family had 15 children and moved around, eventually settling near Coffeyville, Kansas, close to Indian Territory.

Several Dalton brothers initially served on the right side of the law. Frank Dalton became a U.S. Deputy Marshal in Fort Smith, Arkansas, but was killed in the line of duty in 1887. His brothers Grattan “Grat” Dalton (born 1861), Robert “Bob” Dalton (born 1869), and Emmett Dalton (born 1871) followed in his footsteps, working as deputy marshals for federal courts and even for the Osage Nation tribal police. Emmett often served as a guard or posseman.

However, disputes over unpaid wages, accusations of horse theft against Grat, whiskey introduction charges against Bob, and other troubles led to their shift. By 1890-1891, after brief stints in California (where older brother Bill Dalton lived), Bob and Emmett returned to Oklahoma Territory and formed the core of the outlaw gang. Grat joined after a controversial conviction for a train robbery he allegedly didn’t commit (alibis placed him elsewhere). Other members included Bill Powers (sometimes called Tom Evans), Dick Broadwell, Bill Doolin, Charley Bryant, George “Bitter Creek” Newcomb, Charley Pierce, and occasionally others.

A separate brother, Bill Dalton (born around 1865-1866), pursued politics briefly but later joined remnants of the group, forming the Doolin/Dalton Gang (also called the Wild Bunch) after the main Dalton brothers’ downfall.

The gang’s activities focused on robbing trains and banks in the Territories. Their first major train robbery attempt came in February 1891, and they pulled off several successful heists in 1891-1892, building a reputation for boldness. Sensational newspaper coverage accused them of crimes far beyond their actual reach, amplifying their notoriety. Bob Dalton, the ambitious leader, sought to outdo legends like Jesse James. He planned what he believed would be their crowning achievement: robbing two banks simultaneously in broad daylight.

On October 5, 1892, five men; Bob, Grat, and Emmett Dalton, along with Bill Powers and Dick Broadwell, rode into Coffeyville, Kansas, the town where the Daltons had once lived and attended school. Allegedly disguised with fake beards and new clothes, they tied their horses in an alley near the jail (their original plan to tie between the banks failed due to street construction).

Just before 9:30 a.m.: Bob and Emmett entered the First National Bank and Grat, Powers, and Broadwell entered the C.M. Condon & Company’s Bank across the street.

Almost immedietly the Townspeople recognized them despite disguises and raised the alarm. Hardware stores armed citizens with rifles and shotguns. A delay at the Condon Bank, where a teller stalled by claiming the safe’s time lock wouldn’t open until 9:30 (though it had no time lock) gave defenders crucial minutes. Across the street, the First National, Bob and Emmett forced employees to fill a sack with cash  around $1,500, unaware the town was mobilizing. Around 9:40 a.m., the shootout erupted as the gang tried to escape. Citizens fired from windows, doorways, and streets.

The ensuing gun battle lasted 12 minutes and around 200 rounds of hot lead were fired in what became known as “Death Alley.” Early casualties included unarmed or lightly armed townsmen: Lucius Baldwin (shot by Bob after a warning), George Cubine (killed while armed), and Charles Brown (shot while reaching for Cubine’s rifle). In Death Alley, intense crossfire erupted. John Kloehr, a skilled marksman, fatally shot Grat through the throat. Bob Dalton was killed while attempting to rally or escape, shot multiple times. Bill Powers fell dead in the alley. Dick Broadwell broke out on horseback but died from wounds about half a mile away. Emmett Dalton, the youngest at 21, was hit 23 times while trying to mount his horse or flee. He survived but was captured and tried.
Emmet pleaded guilty to second degree murder (though he later claimed he never fired a shot) and served 14 years in prison before parole. He lived until 1937, writing books and later working in Hollywood to recount his story.

The Coffeyville disaster effectively ended the original Dalton Gang. Surviving members like Bill Doolin continued as the Doolin/Dalton Gang for a few more years. Coffeyville earned the nickname “the town that stopped the Daltons,” with a museum and memorials preserving the history today.

The Daltons’ brief but intense outlaw career captured the public’s imagination, blending family loyalty, ambition, and the violent end of the frontier era. Their attempt to rob two banks at once remains one of the boldest and most disastrous feats in Old West lore.