“Laughing” Sam Carey – In the Hole in the Wall Gang
The American West, a landscape etched with rugged mountains, vast plains, and the echoes of untamed freedom, holds within its heart the stories of men and women who dared to live outside the constraints of established society. Among these figures, often shrouded in mystery and embellished by folklore, are the outlaws and gangs that roamed the territories, leaving behind trails of daring exploits and whispered legends. One such individual, a name that surfaces in connection with the infamous Hole in the Wall Gang, is “Laughing” Sam Carey.
The Hole in the Wall Gang, a loosely affiliated network of outlaws operating primarily out of Wyoming during the latter part of the 19th century, conjures images of daring train robberies, cattle rustling, and a defiant disregard for the law. The very name "Hole-in-the-Wall" evokes a sense of remote isolation, a sanctuary carved out of the wilderness where these men could evade capture and plan their next audacious move. While the names of Butch Cassidy, the Sundance Kid, and other prominent figures of the Wild West are readily recognizable, the story of “Laughing” Sam Carey, sometimes referred to as Laughing Dick Carey, remains a more enigmatic piece of this historical puzzle.
While the details surrounding “Laughing” Sam Carey‘s life are scarce and often fragmented, his association with the Hole-in-the-Wall is consistently noted in accounts of the gang’s activities. He is mentioned in connection with various exploits emanating from the Hole-in-the-Wall Pass, a geographically strategic location nestled within Johnson County, Wyoming. This pass, characterized by its rugged terrain and hidden valleys, provided the perfect refuge for outlaws seeking to escape the reach of the law. Its remote location made it difficult for law enforcement to penetrate, allowing the Hole-in-the-Wall Gang to operate with relative impunity for a significant period. The mystery surrounding “Laughing” Sam Carey adds to the allure of this period.
The Hole-in-the-Wall Pass itself is a study in geographical defiance. The landscape is a complex tapestry of canyons, mesas, and dense forests, creating a natural fortress that could be easily defended. The pass provided not only a physical barrier against pursuit but also a psychological advantage for the outlaws who knew the terrain intimately. They could navigate the treacherous trails and hidden passages with ease, while those unfamiliar with the area would quickly become lost or vulnerable. The pass served as a vital link in the network of hideouts and supply lines that sustained the Hole-in-the-Wall Gang’s operations.
According to some accounts, “Laughing” Sam Carey‘s involvement with outlaw life began at a young age. It is believed that he initially served as a messenger and camp servant to Butch Cassidy and his burgeoning gang. This early exposure to the outlaw lifestyle likely shaped his future trajectory, instilling in him a sense of adventure, a disregard for authority, and perhaps a certain romanticism associated with the life of a fugitive. This early role provided him with invaluable knowledge of the inner workings of a successful outlaw operation, including logistical considerations, communication protocols, and the importance of loyalty among gang members.
As a teenager, “Laughing” Sam Carey is said to have ridden with a lesser-known outlaw gang led by Otto Chenoworth. This association, however, proved to be short-lived and ultimately unsuccessful. The Chenoworth gang struggled to achieve any significant notoriety or financial gain, and their activities were eventually curtailed when Chenoworth himself was committed to a sanitarium in South Dakota. This unfortunate turn of events effectively dissolved the gang, leaving its members to scatter and seek alternative paths.
Following the disbandment of the Chenoworth gang, “Laughing” Sam Carey reportedly returned to the Hole-in-the-Wall, the legendary outlaw haven that served as a central hub for numerous criminal enterprises. It was here that he became more closely associated with some of the most notorious outlaw gangs of the era, including Butch Cassidy’s Wild Bunch and Black Jack Ketchum’s Gang. His affiliation with these prominent groups solidified his reputation as a seasoned outlaw and further cemented his place in the lore of the Hole-in-the-Wall.
Butch Cassidy’s Wild Bunch, in particular, was renowned for its audacious bank and train robberies, which captured the imagination of the public and instilled fear in the hearts of law enforcement. The gang’s charismatic leader, Butch Cassidy, possessed a certain charm and cunning that allowed him to evade capture for years. The Wild Bunch operated across a vast territory, stretching from Wyoming to New Mexico, and their exploits became legendary, inspiring countless books, films, and television shows.
Black Jack Ketchum’s Gang, while perhaps less widely known than the Wild Bunch, was equally ruthless and determined. Ketchum himself was a notorious train robber and gunfighter, known for his quick temper and unwavering commitment to his criminal pursuits. His gang operated primarily in the southwestern United States, terrorizing railroad companies and engaging in violent confrontations with law enforcement. Ketchum’s eventual capture and execution further solidified his place in the annals of Wild West history.
Despite his involvement with these notorious gangs, “Laughing” Sam Carey managed to avoid capture throughout his outlaw career. This feat, in itself, speaks to his resourcefulness, cunning, and perhaps a degree of luck. He was reportedly well-known within the outlaw community and frequently associated with stories of daring exploits originating from the Hole-in-the-Wall. His nickname, "Laughing," suggests a certain lightheartedness or perhaps a nonchalant attitude towards the risks inherent in his chosen lifestyle.
By 1903, however, the era of the Hole-in-the-Wall Gang was drawing to a close. Increased law enforcement pressure, combined with internal conflicts and changing social dynamics, led to the gradual disintegration of the outlaw network. Many of the gang members were either killed in shootouts with lawmen or apprehended and sentenced to long prison terms. While “Laughing” Sam Carey managed to evade capture, he, too, eventually faded from history, leaving behind a legacy shrouded in mystery and speculation.
The fate of “Laughing” Sam Carey after 1903 remains unknown. Some speculate that he may have quietly settled down under an assumed name, seeking to escape the notoriety of his past. Others believe that he may have continued to engage in criminal activities, albeit on a smaller scale and in a more discreet manner. Still others suggest that he may have met an untimely end, succumbing to the dangers and violence that characterized the outlaw lifestyle. Whatever the truth may be, the story of “Laughing” Sam Carey serves as a reminder of the complex and often contradictory nature of the American West, a land of both opportunity and peril, where legends were born and destinies were forged in the crucible of freedom and defiance. His name adds another layer to the story of the Hole in the Wall Gang.