“Killer Escapes from Psych Hospital with Survival Gear,” read the headline in our local newspaper. I prefer my local news to focus on Little League scores and the status of library construction. I read on.

“A manhunt is underway for William Enman, a dangerous escapee from Ancora Psychiatric Hospital in Winslow, Camden County (NJ), with authorities concerned he could return to Morris County where he killed a father and his 4-year-old son in 1974.”

Enman was found yesterday — well, he returned to the hospital grounds himself. So much for the great escape. But this episode got me thinking about prison breaks. In our third annual ‘10′ issue, Jim Noles wrote a terrific piece recounting some of the more memorable ones. Here are five of them.

1. Ghasr Prison, Tehran, Iran
On December 28, 1978, the Iranian government arrested Paul Chiapparone and Bill Gaylord, two executives of Texas-based Electronic Data Systems Corp., who were working overseas at the time. The Iranians accused EDS of trumped-up bribery charges and threw the two men into Tehran’s notorious Ghasr Prison. Despite American concern for Chiapparone and Gaylord, the Iranian revolution against the Shah grew more and more chaotic, and the United States government seemed powerless to free them.

Enter EDS founder (and sometimes presidential candidate), H. Ross Perot. Taking matters into his own hands, Perot contacted retired Army Colonel Arthur “Bull” Simons, a Special Forces hero who had led a raid on the Son Tay POW camp during the Vietnam War, and asked him to rescue his two employees. Refusing payment for his services, Simons took a volunteer team of seven civilian EDS employees to Tehran, where they set about plotting a rescue. But before they could spring into action, Iranian revolutionaries stormed the prison. Hundreds of prisoners fled in the confusion, including Chiapparone and Gaylord. Shortly thereafter, they linked up with their would-be rescuers at Tehran’s Hyatt Hotel and then escaped overland to Turkey with the aid of an Iranian EDS employee. Inspired by the unbelievable rescue, best-selling thriller writer Ken Follett took his first turn at nonfiction, penning On Wings of Eagles and proving that truth can, in fact, be stranger than fiction.

2. States Model School, Pretoria, Natal
This particular escape joins the ranks of history’s greatest not because of elaborate planning or daring breakaways. Instead, its infamy is solidified by what might have later happened on the future stage of world history had it not occurred.

On November 15, 1899, Boer fighters in the colony of Natal (now part of South Africa) ambushed a British armored train, and, in the ensuing firefight, captured a British war correspondent for the Morning Post. To their delight, the new captive was the brave (some would say foolhardy) and adventurous son of a British lord—a catch with a great deal of leveraging power. But nearly a month later on December 12, the Boers’ prize escaped the school in which he was imprisoned. Despite a price on his head, the plucky escapee successfully stowed away onboard a train, slipped to safety into Portuguese East Africa (now Mozambique), and made international headlines. Within a year, the former prisoner of the Boers had returned to England and embarked on a political career that landed him a seat in Parliament. It also eventually got him a spot at 10 Downing Street, where he served as prime minister of Britain during World War II. His name, of course, was Winston Churchill (above).

3. Yakutsk, Siberia
When Joseph Stalin’s Red Army joined in Hitler’s attack on Poland in 1939, the Russians bagged thousands of Polish soldiers as prisoners. Stalin promptly ordered hundreds of these men executed, while dispatching the rest to his brutal gulag labor camps in Siberia. Among those imprisoned was cavalry officer Slavomir Rawicz. While in Siberia, the resourceful Rawicz befriended the camp commissar’s wife, and with her help, he and six other prisoners managed to escape during a blinding snowstorm.

A journey of epic proportions followed. A Polish teenage girl who had escaped her own camp joined Rawicz’s band, and the ragtag group skirted Lake Baikal, slipped over into Mongolia, traversed the Gobi Desert, and crossed the Himalayas. After a journey of 4,000 miles, the Polish officer and his four fellow survivors staggered into British-controlled India, finally free. Amazingly, the irrepressible Rawicz soon returned to Europe to again battle the Germans. Rawicz’s memoir, The Long Walk, continues to sell well, even though his amazing story has its doubters (some of whom point out its similarity to the Rudyard Kipling story “The Man Who Was”).

4. Libby Prison, Richmond, Virginia
During the American Civil War, the Confederate government turned Richmond’s three-storied Libby & Son Ship Chandlers & Grocers warehouse into what became known as Libby Prison. Not long thereafter, they crammed some 1,200 Union officers into it, many of whom, not surprisingly, spent their stays planning an escape.

But of all the break-out attempts at Libby, the most successful (and most elaborate) was masterminded by Colonel Thomas E. Rose. Using makeshift tools, he and a few fellow inmates tunneled down through a chimney, out of the prison’s rat-infested cellar, underneath a vacant lot, and up into a shed some 50 feet away. Confident in his secretive route, the colonel returned to the prison on February 9, 1864, and led 15 other prisoners through the narrow tunnel and out into Richmond’s unsuspecting streets. Encouraged by Rose’s success, 93 other prisoners quickly squirmed their way to freedom. Of those, an impressive 59 eventually returned to Union lines, making it the largest prison escape of the war. Although two officers drowned in the attempt, and the rest were recaptured, the Confederates couldn’t help being impressed by their enemy’s feat. The Richmond Examiner praised Rose’s “scientific tunnel” and declared his breakout to be an “extraordinary escapade.”

5. Alcatraz, San Francisco, California
Over the course of Alcatraz’s three decades of operation as a federal prison in San Francisco Bay, it earned a fearsome reputation as America’s escape-proof prison. But that didn’t deter the dozens of inmates who attempted to flee “The Rock.” Officially, none of these men succeeded, and at least seven died trying. But if any did pull it off, they were Frank Morris, John Anglin, and John’s brother Clarence.

With the assistance of fellow inmate Allen West, the three men worked for months to carefully enlarge the vent holes in their cells to clear a way to the prison’s roof. On June 11, 1962, after leaving carefully crafted dummy heads in their beds to fool prowling guards, they slipped out of their cells and, under the cover of darkness, reached the island’s rocky shore. Relying on rafts made of their prison raincoats, Morris and the Anglin brothers entered the cold waters of San Francisco Bay to paddle for the mainland.

The following morning, Alcatraz guards discovered their absence and a massive manhunt ensued. But the three convicts were never re-captured. Although the FBI eventually concluded that they must have drowned, their bodies were never recovered. The resulting “what if” scenarios spawned the 1979 Clint Eastwood movie Escape from Alcatraz and, less directly, the annual Escape from Alcatraz triathlon in San Francisco. In the aftermath of the 1962 “escape” event, the federal government closed down Alcatraz the following year.

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For five more great escape stories, visit the mental_floss store to order that issue, which includes lists of “10 Foods You Never Want to Catch Your Parents Eating Together,” “10 Child Prodigies (Who Actually Ended Up Doing Something), “10 Ads Lost in Translation” and much more.