Top 10 Largest Prison Escapes in US History

Ask people to name the greatest prison escape in American history and you will hear the same three answers: Alcatraz in 1962, the Texas Seven in 2000, and the two convicts who cut their way out of Dannemora in 2015. Add them up and you get twelve men. The breakouts below start where that number ends: the smallest entry involves 11 inmates leaving at once, the largest 109.

Rank escapes by headcount instead of fame and the map redraws itself. The biggest breaks came from a Confederate tobacco warehouse, a Nevada penitentiary whose warden was also the lieutenant governor, a desert POW camp and a Victorian prison in Philadelphia with a 97-foot tunnel under its yard. Most happened before 1950. The ones since almost all came from jails, the county- and parish-run lockups that hold people awaiting trial, not from the state and federal prisons Hollywood prefers. Each entry is tagged [MILITARY PRISON], [POW CAMP], [STATE PRISON] or [COUNTY JAIL], because the type of facility explains more about these breaks than the ingenuity of the men inside.

Methodology

Every entry is ranked by the number of inmates who physically left the facility in one coordinated incident, verified by at least one primary or newspaper-of-record source. Failed attempts, riots without a breakout (Attica in 1971, the Battle of Alcatraz in 1946) and serial escapes spread across weeks do not count. Where sources disagree on the number, the lower, better-documented figure is used and the discrepancy is noted.

The list covers state prisons, county and parish jails, a Civil War military prison and a Second World War prisoner-of-war camp. The last two are flagged because reasonable people exclude them; drop the wartime camps and the Nevada State Prison break of 1871 becomes the largest in US history, as the Nevada State Prison preservation society already claims. Juvenile facilities are handled separately; the 2014 Woodland Hills breakout in Nashville would otherwise rank second.

Ties are broken by how long the manhunt ran. Sources include the New York Times archive, the Associated Press, the Richmond newspapers of 1864 collected by Civil War Richmond, the Indiana Archives and the AFI Catalog. Several of these escapees later appeared on the FBI Ten Most Wanted Fugitives list, created in 1950 in part to catch exactly this kind of man.

List of the Largest Prison Escapes in US History

10. Kansas State Penitentiary, Lansing, 1933 — 11 escaped [STATE PRISON]

On Memorial Day, May 30, 1933, Warden Kirk Prather was watching an inmate baseball game when bank robbers Harvey Bailey and Wilbur Underhill walked up to him with pistols: four .38 automatics smuggled in by Frank "Jelly" Nash inside a bale of sisal fiber delivered to the prison's twine plant. Eleven convicts left with the warden and two guards as hostages, released them near the Oklahoma line with $5 for bus fare home, and scattered across the Southwest.

The Lansing Eleven beat the 11-man Dade County escape of 1974 (see below) on the tie-break because their manhunt ran for months and turned lethal within a day: Officer Otto Durkee was shot dead in Arkansas City, Kansas on May 31 when gang members tried to steal a tire from his car. Bailey was captured in Texas in August 1933; Underhill was shot by federal agents in Shawnee, Oklahoma that December and died of his wounds, according to the Lansing historical society.

Escaped: 11, May 30, 1933. Recaptured: all, over seven months; one officer killed.

9. Walker County Jail, Alabama, 2017 — 12 escaped [COUNTY JAIL]

On Sunday, July 30, 2017, a dozen pre-trial detainees at the Walker County Jail in Jasper, Alabama, facing charges from disorderly conduct to attempted murder, used peanut butter from their sandwiches to change the number painted above a door. A newly hired jailer unlocked what he believed was their cell door. It opened onto the outside. The twelve threw blankets over a razor-wire fence and ran.

"Changing some numbers on the door with peanut butter — that may sound crazy," Sheriff James Underwood told reporters, in remarks carried by the Associated Press. "But these people are crazy like a fox." Six were caught almost immediately, five more within 24 hours, and the last, Brady Kilpatrick, on Tuesday in Tequesta, Florida. The sheriff called the guard "a weak link" who "made a mistake," which is the story of 21st-century jail escapes in one sentence.

Escaped: 12, July 30, 2017. Recaptured: all 12 within about 48 hours.

8. Colorado State Penitentiary, Cañon City, 1947 — 12 escaped [STATE PRISON]

On the night of December 30, 1947, twelve convicts led by Carl Schwartzmiller broke out of the Colorado State Penitentiary at Cañon City, sawing through bars and mixing with prisoners returning from the mess hall. Within a week every escapee had been killed or captured, and three of the twelve were dead, according to production notes preserved in the AFI Catalog.

The details survive because of Hollywood. Within months a crew was shooting Canon City (1948) inside the prison, with real guards and inmates as extras. Life magazine reported that the warden invited eight of the nine surviving escapees to a screening on July 3, 1948; Schwartzmiller was excluded because he had tried to dig his way out again days before.

Escaped: 12, December 30, 1947. Recaptured or killed: all within a week; 3 dead.

7. Eastern State Penitentiary, Philadelphia, 1945 — 12 escaped [STATE PRISON]

Clarence Klinedinst was a plasterer with a long record of good behavior, so Eastern State Penitentiary gave him masonry tools, the blueprints of Cellblock 7 and a ground-floor cell. Over roughly a year he and cellmate William Russell dug a 15-foot shaft and a 97-foot tunnel under the yard to Fairmount Avenue, shored with beams, lit by bulbs and ventilated. On April 3, 1945, Klinedinst went through first; eleven others followed, including the celebrity bank robber Willie Sutton.

Sutton was arrested the same day; four others stole a milk truck and crashed it. Six of the twelve were caught before nightfall and all twelve were back within two weeks, as PhillyVoice recounts. It beats the other 12-man escapes on the tie-break only because its stragglers stayed out longer.

Escaped: 12, April 3, 1945. Recaptured: all 12 within two weeks.

6. Folsom Prison, California, 1903 — 13 escaped [STATE PRISON]

Folsom in 1903 had one design flaw that explains everything that followed: it had no walls. Between 7 and 8 a.m. on July 27, 1903, convicts led by Richard "Red" Gordon attacked their guards, emptied the armory and marched out with Warden Thomas Wilkinson (spelled Wilkerson in the dispatches), his grandson, the captain of the guard and two other officers as human shields. Guard William Cotter was mortally wounded. Contemporary dispatches collected in the Doten diaries give both 13 and 14 escapees; the better-documented figure is thirteen.

Militia and posses from several counties chased the escapees across the Sierra foothills for months, through robberies, kidnappings and killings. Some were caught and tried for murders committed on the run, one was shot dead by pursuers, and five were never found, per the Arcadia Publishing summary of historian Josh Morgan's research. Folsom built its granite wall afterward.

Escaped: 13 (some reports 14), July 27, 1903. Never recaptured: 5; one guard killed.

5. West Virginia Penitentiary, Moundsville, 1979 — 15 escaped [STATE PRISON]

On November 7, 1979, fifteen prisoners broke out of the Gothic stone penitentiary at Moundsville at once. One of them, Ronald Turney Williams, serving time for murdering a Beckley police sergeant, stole a guard's weapon on the way out. Outside, 23-year-old State Trooper Philip Kesner, off duty and driving past with his wife, tried to intervene. The escapees pulled him from his car and Williams shot him; Kesner returned fire as he died. The New York Times reported two days later that eight of the fifteen had been captured and one found dead.

Williams stayed free for 19 months, was accused of a murder in Arizona, and joined the FBI Ten Most Wanted on April 16, 1980. Federal agents cornered him at a Manhattan hotel on June 8, 1981 after a shootout; Arizona later sentenced him to death.

Escaped: 15, November 7, 1979. Recaptured: 8 within two days; last fugitive caught June 8, 1981; one trooper killed.

4. Orleans Parish Prison, New Orleans, 1968 — 21 escaped [COUNTY JAIL]

On December 23, 1968, the New York Times ran the headline "21 Prisoners Flee New Orleans Jail," reporting a break from the old Orleans Parish Prison. By the records available, that makes it the largest single escape from any American jail and the fourth largest from any facility.

It is also the least documented entry here. The Times archive confirms the count and date, and New Orleans station WWL cited it in May 2025 as the city's largest jailbreak, but full accounts of the method and recapture have not been digitized and are not invented here. The parish prison was facing a class-action suit over its conditions by 1969, and the city's jail has spent most of the decades since under lawsuits and federal monitoring.

Escaped: 21, December 1968. Recapture record: incomplete.

3. Camp Papago Park, Arizona, 1944 — 25 escaped [POW CAMP]

The largest breakout of Axis prisoners from any American facility in the Second World War was pulled off by U-boat crews who had never seen a desert. Camp Papago Park outside Phoenix held about 3,100 German prisoners under 371 American guards. Led by Captain Jürgen Wattenberg, the prisoners dug a 178-foot tunnel, and on the night of December 23, 1944, twenty-five men crawled through it into the Sonoran Desert, some carrying a collapsible boat they planned to float down the Gila River to Mexico.

The Gila turned out to be dry. Hunger, cold and rain drove most to surrender within days; others were picked up by Tohono O'odham scouts near the border, and Wattenberg was caught after asking a Phoenix street cleaner for directions. The last man was back in custody on January 28, 1945, 36 days after the break, without a shot fired. Their punishment, per the camp history, was bread and water for as many days as they had been gone.

Escaped: 25, December 23, 1944. Recaptured: all 25 by January 28, 1945.

2. Nevada State Prison, Carson City, 1871 — 29 escaped [STATE PRISON]

Nevada's warden in 1871 was Frank Denver, who held the job because he was also the lieutenant governor. On Sunday evening, September 17, 1871, convicts overpowered the single guard left to lock them in, and when Denver came down with a derringer and shot the ringleader, they seriously wounded him, broke into the armory and left with Henry rifles, shotguns, revolvers and up to 3,000 rounds of ammunition. Twenty-nine men walked out. A Pony Express rider, Billy Poor, was shot dead near Sulphur Springs, apparently to stop him spreading the news, and guard F.M. Isaacs died of his wounds.

On September 23, a posse caught a group of escapees in Monte Diablo Canyon; Wells Fargo agent Robert Morrison and a Paiute tracker known as Mono Jim were killed in the shootout, and the lake there has been called Convict Lake ever since. Several convicts captured afterward were lynched on the way back. By November 1, 18 of the 29 had been returned; the remaining 11 were never found. The Nevada State Prison Preservation Society calls it the largest prison break in American history, which holds if you exclude wartime prisons.

Escaped: 29, September 17, 1871. Recaptured: 18; 11 never found; at least four people killed.

1. Libby Prison, Richmond, Virginia, 1864 — 109 escaped [MILITARY PRISON]

Libby Prison was a tobacco warehouse on the James River that the Confederacy turned into an officers' prison in 1861; by 1863 it held around 1,000 Union officers. Colonel Thomas E. Rose and Major A.G. Hamilton found their opportunity in "Rat Hell," an abandoned basement kitchen so infested with rats and so prone to flooding that the guards refused to enter it. Working in relief teams, they dug for 17 days with improvised tools, failing twice, until the third tunnel broke through beneath a carriage shed in a vacant lot about 50 feet away.

On the night of February 9-10, 1864, 109 officers went through it. The Richmond Examiner, quoted by Civil War Richmond, reported that they "crawled from their prison-house into the open air unobserved by any one"; the Confederates did not notice until morning roll call, nearly 12 hours later. Of the 109, 59 reached Union lines, 48 were recaptured (Rose among them) and 2 drowned in the James. Nothing in American history has come close since.

Escaped: 109, February 9-10, 1864. Reached Union lines: 59; recaptured: 48; drowned: 2.

Summary of the Top 10 Largest Prison Escapes in US History

The Ones That Just Missed, and the Ones Everybody Remembers

Three escapes fell one or two men short of the table.

Dade County Jail, Miami, September 19, 1974 — 11 escaped. Thomas Knight, awaiting trial for murdering a Miami couple, led ten other prisoners out. Eight were recaptured within two days; Knight killed a liquor-store clerk in Georgia on October 21 and was taken by an FBI SWAT team in New Smyrna Beach on December 31, 1974, per the case history on Wikipedia. It loses the tie with Lansing only because its manhunt was shorter.

Indiana State Prison, Michigan City, September 26, 1933 — 10 escaped. Engineered from outside by a parolee named John Dillinger, who hid three .45 pistols in boxes of thread shipped to the prison shirt factory. Ten men got out, among them Harry Pierpont, Charles Makley and Russell Clark, who repaid the favor on October 12 by freeing Dillinger from the Lima, Ohio jail and killing Sheriff Jess Sarber. The core of the gang was captured in Tucson on January 25, 1934, per the Indiana Archives.

Orleans Justice Center, New Orleans, May 16, 2025 — 10 escaped. Shortly after midnight, ten inmates in a jail holding about 1,400 people worked a faulty sliding door off its track, ripped out a toilet, cut the bars behind it, scaled a wall and sprinted across Interstate 10, leaving "To Easy LoL" scrawled above the hole. The pod's guard had stepped away for food, and the break was not discovered until the 8:30 a.m. head count, roughly seven hours later, per NBC News. Three were caught the same day; a maintenance worker was arrested for allegedly shutting off the water; 16 people were charged as accessories; and the last escapee, Derrick Groves, serving life for a Mardi Gras double murder, was pulled from a crawl space under an Atlanta house on October 8, 2025, CBS News reported. Sheriff Susan Hutson was indicted over the escape in April 2026. It is the largest American jailbreak of the 2020s, and still two men short of the top ten.

Then there are the famous ones. The Texas Seven (December 13, 2000) overpowered staff at the Connally Unit, stole 14 handguns, a shotgun and an AR-15, murdered Irving police officer Aubrey Hawkins on Christmas Eve and were run to ground in Colorado in January 2001. Mecklenburg, Virginia (May 31, 1984) saw six death-row inmates, including the Briley brothers, bluff their way out with a fake bomb. Clinton Correctional, Dannemora (June 6, 2015) involved two men and a $23 million manhunt; Alcatraz (June 11, 1962) involved three. All four are more famous than anything in the top ten. None would make a top thirty.

If juvenile facilities counted, the list would need rewriting: on September 1, 2014, 32 teenagers crawled under a fence at Woodland Hills Youth Development Center in Nashville, nearly half of a facility holding 78 boys, and 13 more escaped three weeks later, per the Guardian and CNN. Louisiana keeps adding entries: eight inmates left the Riverbend Detention Center in Lake Providence before dawn on January 30, 2026, and all were back in custody within 24 hours, per the Associated Press.

What the Headcount Reveals

Two patterns emerge that the famous escapes hide.

The mass escape is a 19th- and early-20th-century phenomenon at prisons, and a 21st-century phenomenon at jails. Six of the ten entries, and every one above 13 men, happened before 1950, at facilities with no walls (Folsom), one guard on duty (Nevada), a basement nobody would enter (Libby) or a tunnel nobody looked for (Papago, Eastern State). Modern prisons were designed to prevent exactly this, and they do: the largest state-prison escape since 1980 that we could document is the Texas Seven. The vulnerability moved to the county lockup. Walker County in 2017, Clovis, New Mexico in 2008 (eight out through the roof), New Orleans in 2025 and Lake Providence in 2026 were all sheriff-run jails holding pre-trial detainees, New Orleans' staffed at about half the level its sheriff said she needed. The pattern is sharpest in cities on our list of the most dangerous cities in the US, where jails are oldest, fullest and most litigated.

Almost everyone gets caught, and the ones who were not were saved by geography. Of the roughly 260 people who escaped in the ten incidents above, the only ones who stayed free were Civil War officers who reached their own army and the 1871 and 1903 convicts who vanished into a West with no telephones, fingerprint files or state police. Since 1933 the record is close to perfect: every Lansing escapee, Eastern State tunneler, German POW, Walker County detainee and 2025 New Orleans fugitive ended up in custody or dead. The modern fugitive is undone by phone calls (the Brileys), television (the Texas Seven), relatives (New Orleans) and having nowhere to go. That is why the most durable names on today's wanted posters are not escapees but the most wanted cybercriminals, who never had to leave a building.

The practical takeaway for the next breathless jailbreak headline is to ask three questions: how many got out, what kind of facility was it, and how long until the last one was caught. By those measures the great American prison break is not Alcatraz, which lost three men to the bay. It is a tobacco warehouse in Richmond where 109 officers walked into the dark through a hole in a rat-infested cellar.