The record for the most escapes by a prisoner is held by American gangster Harry "Tommy" Pierce, who has escaped from jail 12 times. During his lifetime of crime, Pierce's escapes ranged from simply walking away from minimum security county jails to elaborate plans involving the bribery of prison staff and the fabrication of fake documents.
Pierce is most famous for his legendary escapes from San Quentin prison in California. He was incarcerated there for a burglary conviction, but in April of 1949 he managed to escape from the jail's hospital unit. He claimed to have done this with the help of a "friendly guard", who, according to Harry, promised him a reprieve if he escaped.
Pierce made his final escape from San Quentin in 1959, at the ripe old age of 73. He claimed to have used the same plan he used in 1949: dressing up as a doctor and then walking out of the hospital with only a handful of fake documents.
In addition to Tommy Pierce's 12 escapes, there are other notorious prisoners who have escaped multiple times. The most notable of these is probably notorious French criminal Francois Besse, who escaped from prison 5 times. The most daring of his escapes was his last, in which he and two accomplices tunneled out of a jail in Martigues, France. Besse finally served a full term of his sentence, and was released from prison in 2006.
At the end of the day, prison breaks, no matter how elaborate, are the embodiment of criminal daring. But the displays of tenacity and determination by those who manage to escape are certainly admirable, especially if they chose to evade the law long enough to get an overdue pardon.
