Al Capone is perhaps one of the most notorious old-school gangsters ever to terrorize Chicago. His crew made more than $100 million per year via their shady business dealings and numerous murders.

Capone was eventually charged with tax evasion and sent to the notorious Alcatraz prison of San Francisco. What many are unaware of was that he was a completely broken man following his stint in prison.

When released, prison guards and prisoners alike shared numerous stories about Capone’s activities behind bars. For example, he played the banjo in a prison band, was constantly harassed/threatened by other inmates, and would often hunker down in the corner of his jail cell. It was even reported that he would sometimes mumble to himself and talk like a baby.

Was it that his years of crime made him go mad? Or his horrid life on Alcatraz? Both of these factors could have played a role, but there was something more profound and damaging going on within his brain.

It was later revealed that Capone had contracted syphilis at the age of 18, but decided to ignore it. In the last year of his 10 year sentence, things got even worse. On February 5, 1938, Capone was discovered by a fellow prisoner sitting in his cell wearing his winter coat, cap, and gloves.

When the prisoner tried to interact with him, Capone didn’t seem to recognize him. He stared off into space seemingly without a care in the world. Guards ordered him to fall into line, but he didn’t follow their orders. As punishment they sent him to the hole, and it was then that the guards realized it was so much more than him choosing to ignore their orders.

The horrific truth was that Capone’s brain was slowly being eaten alive by his untreated syphilis. When he was let free from the hole, Capone wandered into the mess hall and was drooling all over the place. It was also reported that he moved mechanically and approached the deputy warden, Ernest Miller. Capone gave him a very strange grin and then pointed out the window. The warden realized that he may have been indicating he needed to go to the hospital ward.

It was soon discovered that Capone’s brain was being eaten away due to his advanced syphilis. Shortly after his moment of seeming insanity, the former mob boss had a moment of lucidity and agreed to a spinal puncture and various tests.

Somehow the press discovered that Capone was losing his sanity and blamed it on his horrible life at Alcatraz. They didn’t have a clue that it was syphilis, but told the world that he couldn’t hack prison life.

This inspired his wife Mae Capone to call the warden and ask for her husband to be freed. Pity was taken on Capone and he was sent to the hospital ward until he was officially released from Alcatraz. During his moments in the hospital ward, he went back and forth between lucidity and pure confusion.

Capone was finally released from Alcatraz in January of 1939 and then sent to Terminal Island near Los Angeles to serve another sentence.

Once released, he lived his last years in his estate near Miami. During that period, his mental state was challenged and he became quite paranoid. He would also sit with a fishing pole and cast it into his swimming pool, hoping to catch fish that didn’t exist.

He eventually died after complications related to a brain hemorrhage that made him collapse.

The following video explains a heck of a lot more surrounding Capone and his struggles.