Alphonse "Al" Capone, the Chicago crime boss whose rise to national notoriety in the 1920s and early 1930s symbolized organized crime’s expansion during Prohibition, was incarcerated on federal charges including tax evasion. Convicted in 1931, Capone served much of his federal prison sentence in the U.S. Penitentiary, Atlanta, before being transferred to Alcatraz in August 1934, where the Bureau of Prisons placed high-profile, dangerous, or escape-prone inmates. Capone’s health deteriorated while incarcerated. In the late 1930s he began to exhibit symptoms of neurosyphilis, a progressive condition that affected his cognition and physical health. Medical evaluations documented cognitive decline and other neurological signs, and his condition became a central factor in decisions about his custody. By the late 1930s and into the early 1940s, federal officials moved Capone out of the high-security Alcatraz environment for medical reasons and to facilitate transfer for further treatment. Official records show that Capone was released from Alcatraz to the custody of federal authorities for transfer and medical care rather than as an unconditional freeing based on pardon. After his removal from Alcatraz, Capone was transferred to a hospital and then to other federal facilities; he ultimately was released from federal prison in 1939 on the basis of good behavior and time served, compounded by his incapacitating illness. Following release, he returned to Florida, where he lived with relatives and private caregivers until his death in 1947. Capone’s release is often recalled as an intersection of criminal justice policy and medical compassion: federal authorities balanced the need to confine a notorious criminal with the practical considerations of providing adequate medical treatment. Historical sources emphasize that his removal from Alcatraz was driven by medical findings—most prominently neurosyphilis-related deterioration—and administrative decisions about appropriate placement and care. The case also illustrates broader themes of the era: the federal government’s evolving approach to high-profile prisoners, the limits of incarceration when confronted with severe illness, and the public fascination that accompanied prominent criminal figures even after conviction. Because contemporary reporting and later historical treatments sometimes conflate Capone’s various transfers and the dates of his final discharge from different facilities, accounts can vary in specifics about exact transfer dates. Primary sources such as Bureau of Prisons records, contemporaneous newspaper reports, and later scholarly biographies provide the basis for the timeline: conviction in 1931, transfer to Alcatraz in 1934, medical decline in the late 1930s, and ultimate release from federal custody in 1939 with subsequent residence in Florida until his death in 1947. Where exact day-by-day details differ among sources, the consensus centers on medical incapacity as the decisive factor in his removal from Alcatraz and eventual release. Capone’s final years were quiet compared with his public life in Chicago; incapacitated by disease, he did not return to organized criminal leadership. Historians continue to study his case for what it reveals about law enforcement, public perceptions of crime, and the interaction of health and punishment in the American penal system of the period.