Autograph signatures and signed letters of outlaws and criminals have always fascinated collectors , but the short life spans and long prison terms endemic to this career pursuit, along with illiteracy, have made their autograph signatures and any other signed pieces very rare. Jesse James left fewer autograph pieces than he did victims, and it would be a once in a lifetime opportunity if one were to become available. Jesse’s brother, Frank James, his compatriot in outlaw pursuits, survived, and after a prison term, he repented his outlaw ways. He did not give autograph signatures to people, but he did write letters that have been saved, and although quite rare, they occasionally become available. The other famous outlaws of this period all died violent deaths or did not survive prison, with the exception of Emmett Dalton, who did write signed letters after his release from prison. They are quite rare, but it is possible to find one.
Autograph signatures and other signed pieces of the great bank robbers and gangsters of the 1920s and 30s are all very rare. John Dillinger signed only a few letters and other pieces, and while Al Capone may have been willing to sign autographs, it does not appear that many people had the nerve to ask him. Bonnie and Clyde are almost unknown in autograph signatures
Many of the lawmen from the 19th century were straddling both sides of the law, but the fact that they were on the right side at some point resulted in signed documents, though all of them are very rare now. Wyatt Earp, Bat Masterson, and Pat Garrett very rarely come on the autograph signature market. The only lawman whose autograph signature and signed letters are plentiful is J. Edgar Hoover, the founding director of the Federal Bureau of Investigation. His long life and his position as head of the FBI resulted in many autograph signed pieces, and a nearly total lack of interest among collectors has caused them to continue to be available.