She and her sister "Queen" Ann Bassett are known for their love affairs and associations with well-known outlaws, particularly Butch Cassidy's "Wild Bunch".
Both girls were sent to prominent boarding schools in their youth, but both chose to return to the ranching life by their teen years.
Among those who visited the Bassett ranch were "Black Jack" Ketchum, Butch Cassidy, Elzy Lay, Kid Curry, Will "News" Carver and Ben Kilpatrick.
[citation needed] When Cassidy was sent to prison for 18 months, starting in 1894, Ann became involved in a relationship with Ben Kilpatrick.
That was the complicated circle of relationships that developed between the Bassett girls and Cassidy's Wild Bunch gang.
Despite the seemingly constant changes in romantic companions by both the Bassett girls and the gang members, there is no indication that any animosity ever resulted from it.
Josie Bassett was reportedly one of only five women who were allowed into the outlaw hideout called "Robbers Roost", located in Utah; the others were her sister Ann, the Sundance Kid's girlfriend Etta Place, Elzy Lay's wife Maude Davis, and Will "News" Carver's girl Laura Bullion.
Those outlaw relationships, as well as the Bassett ranch's supply of beef and horses to the gang, assisted the sisters in their time of need.
One legend indicates that Kid Curry, easily the most feared of the Wild Bunch gang, approached several of the cowboys known to work for the cattlemen and warned them to leave the Bassetts alone.
Although Cassidy is reported to have been killed in Bolivia, Josie claimed that he visited her in 1930 and lived in Utah until the late 1940s.
She was the last remaining associate of the Wild Bunch gang as well as the last direct source of information about its members, their personalities, and traits.