Alcatraz wasn't known for its medical staff, but doctors on The Rock eventually realized there was some funny business going on with Capone. Doctors noted that he'd sit quietly with a "strange grin" on his face, and that he'd sometimes put on his coat, hat, and gloves while sitting in his heated cell. Left untreated for years, Capone's syphilis rendered him insane, and by the time he was paroled for (ironically) "good behavior," doctors estimated that he had the remaining mental capacity of a 12-year-old.

And while syphilis was Capone's get-out-of-jail-free card, it was the treatment for gonorrhea which led to John Dillinger's attempts to get out of jail. When he was sentenced to prison in 1924 (before he became really famous), doctors discovered that Dillinger had the clap, the treatment for which was invariably worse than the symptoms.

New York: International Journal of Surgery

Because doctors are obliged to treat good guys and gangsters alike, Dillinger received 1924's top-notch clap cures, which are enough to make a frat boy celibate. Basically, they injected silver nitrate into the patient's urethra, either by straight-up squirting it into the penis or running a long, thin metal rod run up there. Fun! By the end of his first 90 days in prison, Dillinger tried to escape so many times that officials had extended his overall sentence by a year. And while we're not saying this irrevocably turned him to the life of crime that made him famous, ask yourself how many banks you thought society owed you after you had something forcibly put in your urethra. More than zero, right?

Officially, Lenin's death was caused by cerebral atherosclerosis (a hardening of arteries in the brain), but both of Lenin's personal physicians refused to sign the death certificate. He was treated by a German syphilis specialist who wouldn't confirm his condition outright, but said, "Everyone knows for what brain disorder I am called." Additionally, in 1922, Lenin was given the arsenic-based drug Salvarsan, which was used to treat exactly one condition: syphilis. One person who had the gumption to discuss Lenin's syphilis directly was Ivan Pavlov, of dog experimentation fame. When offering his opinion on Russian politics, Pavlov said, "[the] revolution was made by a madman with syphilis of the brain."

So what difference does it make how Lenin died? Quite a bit. Since he was only 53 when his ticket was punched, it's reasonable to assume he'd have otherwise continued leading Russia for another decade or two. Instead, Joseph Stalin was left to take command. Who knows how things would have shaken out if Lenin had lived? Perhaps Leon Trotsky, not Stalin, would have been his successor.

Russian Federation

Prior to his death, Lenin pointed out a number of Stalin's perceived shortcomings, and even recommended that he be removed from office. But Stalin was a devious bastard and easily outmaneuvered Trotsky, even making sure he missed Lenin's funeral by giving him the incorrect date. Once Stalin was officially in power, Trotsky was dismissed, exiled, and eventually assassinated, and Stalin would stay in charge for a full 30 years, during which a bit of game-changing history was made.

Apparently, Hill's West Point education included some advanced "flanking maneuvers," and he picked up the clap while on furlough in New York City in 1844. Since there was no cure for the disease at the time, it had an unfortunate way of cropping up and affecting his performance at inopportune moments. One general described him as a "prodigy" at his best and "disappointing" and "lackluster" at his worst.

Hill spent most of the first day of the Battle of Gettysburg unwell and confined to his cot, looking "very delicate" to all who saw him. Things didn't go well in his absence from his men; under strict orders from General Lee not to engage in battle, Hill's subordinates did exactly the opposite. When Lee asked Hill why there were sounds of battle coming from the east, "the obviously ill corps commander claimed ignorance and mounted his horse to investigate." Later, though his corps made up the majority of the famous Pickett's Charge, Hill wasn't placed in command of the action, and also sort of forgot to mention (or simply didn't know) how badly beaten up those troops were. His corps suffered the most casualties during the ill-fated battle, and led the retreat back into Virginia.

Would fresh troops during Pickett's Charge, or a mentally sound general, or a condom years earlier, have resulted in the South winning the Civil War? Hard to say. But we are on board with the condom thing, in case you're furloughing in New York this year.