The Most Notorious Prison Breaks in Recent History

Man escaping by climbing rope over wall

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Danelo Cavalcante’s not the only one to pull off an unbelievable escape.

After nearly two weeks on the loose, Danelo Cavalcante has finally been apprehended. The 34-year-old, who escaped from Chester County Prison in Pennsylvania by crab-walking up to the roof, evaded authorities for nearly two weeks. 

Cavalcante, who was sentenced to life behind bars for murdering his former girlfriend, was spotted several times before he was finally taken back into custody. While on the run, officials say the 34-year-old stole a dairy delivery van and later a .22 rifle from a homeowner’s garage. 

He was finally cornered after a U.S. Drug Enforcement Administration aircraft picked up a heat signal they suspected could be given off by the fugitive. Agents surrounded Cavalcante, who fled but was ultimately subdued with help from a U.S. Border Patrol tactical unit dog, NBC reports

“He was desperate, and it was just a matter of time,” Pennsylvania Gov. Josh Shapiro said

The getaway is one of the most sensational jailbreaks in recent history. Here’s a look at some other infamous escapees.

Most Famous Prison Escapes

Escape from Dannemora, 2015

David Sweat (left) and Richard Matt (Getty Images)

Two convicted murderers, Richard Matt and David Sweat, broke out of the Clinton Correctional Facility in Dannemora, New York with the help of Joyce Mitchell, a prison employee who had become romantically involved with both men. 

“She professed her love for Sweat in notes she secretly sent him,” a report from the New York inspector general reads. Mitchell also allegedly “engaged in numerous sexual encounters with Matt in the tailor shop,” which she supervised. 

She allegedly smuggled chisels, hacksaw blades, and other tools in frozen hamburger meat, which were delivered to Seat and Matt by guards. The pair used the implements to cut through the steel in the back of their cells and climb down several stories. They then cut a hole through a steam pipe and crawled through a manhole. A few weeks later, Matt was shot and killed by police, while Sweat was captured two days later.  

El Chapo, 2015

El Chapo as he’s being transported to prison in Mexico City. (Getty Images)

Joaquín Guzmán Loera, the Mexican drug kingpin better known as El Chapo, disappeared down a two-by-two foot hole in his cell. The opening was connected to a sophisticated mile-long tunnel, which was ventilated, equipped with lights, and even housed a motorcycle. Some engineers estimate it took more than a year for Guzmán’s associates to build and cost at least $1 million, the New York Times reports

The drug lord was free for nearly six months, during which time he managed to meet and be interviewed by the actor Sean Penn. Following a massive manhunt, Guzmán was finally captured in Sinaloa in January 2016. He was extradited to the U.S. where he was sentenced to life in prison for drug conspiracy.

Texas Seven, 2000

Top row, left to right: Joseph Garcia, Randy Halprin, Larry Harper, Patrick Murphy Jr. Bottom row, left to right: Donald Newbury, George Rivas, Michael Rodriguez.

In December 2000, seven men who were serving time in a South Texas prison ambushed guards in the facility’s maintenance shop. They stole civilian clothing and guns and fled in a prison pickup truck. They left a note, which read: “You haven’t heard the last of us yet.”

While loose, the fugitives robbed a Radio Shack and a sporting goods store where they shot and killed a police officer. They spent a month in a motor home in Colorado, trying to pass as religious missionaries. Six of the men were captured, while the seventh died by suicide before he was taken into custody.

Ted Bundy, 1977

ted bundy
Ted Bundy (Getty Images)

One of America’s most infamous serial killers escaped custody — twice. The first time Bundy, who confessed to murdering 30 people, broke free was at a courthouse in Aspen, Colorado in 1977. He chose to represent himself at a preliminary hearing and during a recess asked to visit the facility’s law library on the second story for research. 

“The guard went outside for a smoke,” Bundy told prison psychologist Dr. Al Carlisle. “The windows are open, and the fresh air is blowing through. And the sky was blue, and I said, ‘I’m ready to go,’ and walked to the window and jumped out.” 

He injured his ankle from the fall, but still managed to hike into the surrounding mountains, where he broke into a cabin and stayed for several days. Bundy then stole a car and was eventually pulled over for driving erratically. He was brought back into custody after six days on the loose. 

He broke free again a few months later by squeezing through a grate in his jail cell. He reportedly carved the opening in his ceiling and lost about 20 pounds so he could fit through. Bundy then crawled through the duct and came down into one of the guards’ apartments, donned his clothes, and escaped.  

He then flew to Chicago, took a train to Ann Arbor, Michigan, drove to Atlanta, and headed to Tallahassee, Florida via bus. He killed three more people in the Sunshine State before he was finally apprehended, about a month and a half after he escaped. 

In January 1989, Bundy was executed by electric chair. 

Escape from Alcatraz, 1962

alcatraz cell
One of the cells from which the pair escaped. (Getty Images)

Frank Lee Morris and brothers Clarence and John Anglin escaped from the maximum-security prison, known as “the Rock,” nearly 60 years ago. The three men, who had been convicted of bank robbery, placed papier-mâché heads they constructed into their beds and are thought to have escaped through a kitchen smokestack, The Hill reports

The trio then took off into the San Francisco Bay on a raft they made by stringing 50 raincoats together. They were never seen or heard from again. Authorities insisted that the Anglins and Morris, who had also broken out of Louisiana State Penitentiary, couldn’t have survived the rough waters, but scientists simulating the currents say there’s a chance they could have made it to shore, AP reports.