Our Arklahoma Heritage: The son of a prominent Madison County man killed his girlfriend, brother, and romantic foe in 1933
On the morning of October 29, 1933, the quiet of the little village of Alabam in Madison County, Arkansas, was shattered by violence. Twenty-year-old Herbert Holland, driven by jealousy and fueled by alcohol, stormed into his brother’s home and opened fire with a shotgun. Within minutes, three young lives were gone, and the community was left reeling from the horror.
Herbert walked into the dining room armed with six shells and his brother Clarence’s 12-gauge automatic shotgun. Inside, Clarence Holland, age 33, sat with seventeen-year-old Naomi Bailey and eighteen-year-old William “Will” Boatright, along with Herbert’s sister, Emma Mullins, and a friend, Keith Denny.
Without warning, Herbert raised the gun and pulled the trigger. Naomi was the first target. Struck in the chest, she ran to a bedroom but collapsed and died on the floor. Will was shot next, a blast tearing into his side as he fled to the same room. He collapsed on the bed and died moments later.
Clarence tried to escape but was struck twice--once in the elbow and again in the side. He staggered to the front room and fell dead in the doorway.
Herbert’s rage spared no one from terror. He pointed the gun at Emma, telling her he would not kill her but would “save her for a purpose.” Keith managed to escape the house altogether.
In a chilling act, Herbert returned to the bedroom where Will lay dead and fired another shot into his face, though witnesses confirmed he was already gone. Leaving the shotgun in the yard, Herbert calmly sat on the porch, waiting for the law.
When a passerby came by, Herbert asked him to fetch the sheriff, admitting he had killed three and was ready to accept punishment.
The motive behind the bloodshed lay in a bitter mix of jealousy, heartbreak, and family tension. Herbert had been courting Naomi Bailey, who was living with Clarence after her sister’s death. But Naomi had rejected him and instead given her affections to Will Boatright.
Herbert believed Clarence, his own brother, had encouraged her change of heart, and he could not bear the betrayal. Combined with heavy drinking, his emotions erupted into violence.
Herbert came from a respected Madison County family. His father, S. S. Holland, was a postmaster and merchant in nearby Rockhouse. After his arrest, Herbert at first refused to let his photograph be taken but later relented once clean clothes were provided at the Berryville jail.
The victims left behind grieving families who were well-known in the area. Clarence Holland was a widower who had acted as guardian to Naomi. His parents, Mr. and Mrs. S. S. Holland, mourned the loss of their eldest son.
Naomi Bailey’s death at only seventeen devastated her mother, Jessie Bailey, and her brothers and sister, James, Hugh, Walter, Clyde, and Clara.
Will Boatright, just eighteen, was the son of William Amos “W. A.” Boatright, a farmer and bank director, and Lela Vista Montgomery Boatright, a schoolteacher. He left behind siblings Ruth, Marie, Joseph, Betty Jean, and Bertie Lee. Will was laid to rest in the Alabam Cemetery beside his parents.'
Funeral services for the three victims were held on November 2, 1933. The services, led by local ministers, gave the shaken community a chance to mourn together.
After his arrest, Herbert freely confessed to the murders. He told officers that he felt mistreated, that he had been seeking revenge, and that he was ready to “pay the price.”
A jury convicted him and sentenced him to life in prison. But his case took strange turns in the years that followed.
Under Governor Junius Marion Futrell, Herbert was granted a one-year furlough from the Boys Industrial School, a reform facility for young offenders. The reasons for this temporary release remain unclear, though it may have been seen as a chance for rehabilitation.
When Governor Carl Edward Bailey took office in 1937, he ordered Herbert’s return to custody, ending the furlough and reinforcing a harsher stance on crime.
The Boys Industrial School itself was known for troubled conditions and would later be infamous for the deadly Wrightsville fire in 1959. Herbert’s time there highlights the uneven approach to justice in Arkansas during the Depression era.
What ultimately became of him--whether he remained in prison or received further leniency--has been lost to incomplete records, leaving part of the story unresolved.
Today, the 1933 Alabam triple slaying lingers as a grim memory in Madison County’s past.
The graves of Clarence Holland, Will Boatright, and their families rest in Alabam Cemetery, quiet witnesses to the tragedy. Local archives may still hold more answers about Herbert’s fate, but the story remains one of jealousy turned deadly and justice that shifted with the times.
It serves as a reminder of how fragile life was--and still is--when anger overtakes reason in the Arkansas hills.
