Police Officer James Worden Fagan

Police Officer James Worden Fagan

Ossining Village Police Department, New York

End of Watch Monday, April 14, 1941

James Worden Fagan

Police Officer James Fagan was shot and killed while he and another patrolman were attempting to arrest three convicts who had just murdered Guard John Hartyre of the New York State Department of Corrections during a prison break from Sing Sing Prison. One of the convicts was shot and killed and the other two were arrested.

The two who were arrested were convicted of murdering Guard Hartyre, sentenced to death, and both were executed on June 11th, 1942. Neither prisoner was tried for murdering Officer Fagan.

Officer Fagan had served with the Ossining Village Police Department for seven years. He was survived by his wife and son.


  • Age 35
  • Tour 7 years
  • Badge 13

Incident Details

  • Cause Gunfire
  • Weapon Gun; Unknown type
  • Offender Executed in 1942

Most Recent Reflection

View all 8 Reflections

Article in the NY POST April 13, 2015

Annual Sing Sing prison event honors guard John Hartye and police officer James Fagen who were fatally shot by prisoners in jail break

Officer James Fagan was also killed by the prisoners in shootout.
Officer James Fagan was also killed by the prisoners in shootout.
Later this month, a sunrise ceremony at the gates of Sing Sing prison will salute a guard and a local cop who died nearly 75 years ago in a breakout suitable for a “Mission: Impossible” plot.

The names of the victims, prison guard John Hartye and Ossining Officer James Fagan, faded from the front pages long ago. The annual event at Sing Sing serves as a reminder of who they were and how they died.

“It’s always good to remember those who made the ultimate sacrifice to keep their communities safe,” said Clarence Fisher Jr., a vice president of the state correctional officers union.

But Fisher said the ceremony will have special resonance this year, after inmate keepers from Attica to Rikers Island have been buffeted by brutality charges.

Hartye’s murder “tells the other side of our story,” Fisher said.

“When you work behind the walls, nobody outside really sees what this job is about — the positive stuff you’re doing for inmates, the danger you face,” said Fisher. “All you get is the ‘bad prison guard’ story.”

About 35 state prison employees have been killed on the job in New York, including 11 during the Attica riot in 1971.

Hartye died 30 years before Attica during an escape that proved just how porous the old joint had become.

Three Sing Sing jailbirds and two outside pals spent nine months plotting an exacting escape.

New York Daily News
Joseph Riordan (l.) and Charles McGale in police custody.

The convicts — Joseph (Whitey) Riordan, 27; John (Patches) Waters, 30; and Charles McGale, 46 — were part of a Hell’s Kitchen robbery crew, the Paper Bag Gang, specialists in machine gun-blazing payroll stickups, including an $11,000 heist from Consolidated Edison.

Each was a Sing Sing repeat customer, with criminal records dating to adolescence and stints in the Catholic Protectory and Elmira Reformatory. Parole was a mirage years away.

Waters was the brains. Riordan, a stout ex-stevedore, was the brawn. McGale, who knew as much about locks as Linus Yale himself, was the keysmith.

The men finagled work details in the prison powerhouse and mapped out an escape route along tunnels lined with steam pipes. McGale disassembled barrel locks on basement gates and fabricated new keys to fit them.

Other details were coordinated in whispered asides during six visiting-room confabs between Waters and Edward Kiernan, posing as the con’s loving brother.

Three weeks before the escape, McGale was waiting in the prison icehouse when a milk truck made its daily delivery. As the rig was unloaded, McGale slipped underneath and untied three .38-caliber revolvers strapped to the rear axle.

The gang concealed the pistols until go-time.

Waters, Riordan and McGale bellyached their way into the prison infirmary on Sunday night, April 13. Just two guards were on duty there, including Hartye. An hour after midnight, the cons brandished pistols and shot the unarmed Hartye in the back. The second guard was locked in a closet.

Daily News Photo
Daily News front page on April 15, 1941.

The men hurried downstairs to the steampipe tunnels, where McGale’s keys worked flawlessly on three gates. At the tunnel’s end, they shinnied 30 feet down a rope onto railroad tracks, then dashed for Ossining village, where a stolen Plymouth outfitted with a Tommy Gun was waiting for them.

No alarm had been sounded, and a getaway was within their grasp.

But the cons crossed paths with a two-man police patrol car while slinking toward the Plymouth. Officer Fagan spotted their prison dungarees and called out to the men.

They replied with gunshots that killed the cop. His partner fired back, fatally wounding Waters.

Riordan and McGale didn’t make it to the getaway car. They fled down to the Hudson’s shore and forced a fisherman to row them across the 2-mile wide river, bucking the tide.

Ninety minutes later, the escapees were deposited at the base of Hook Mountain, where they fled into the woods.

As news of the breakout spread, searchers arrived by land, sea and air, and a pair of state police bloodhounds, Sappho and Monk, tracked down Riordan and McGale not long after dawn.

Surrounded, they surrendered their guns. They had been loose for just seven hours.

Charles McGale (pictured) and Joseph Riordan got seven hours of freedom and, soon after, eternity after being executed for killing Officer James Fagan and Sing Sing guard John Hartye.

The felons were hauled back to Ossining, where they got a rough welcome by colleagues of Fagan, a 36-year-old family man, and Hartye, 55, a bachelor.

Just six weeks later, the escapees and accomplices Kiernan and William Wade went on trial in White Plains for Hartye’s murder.

All four were convicted after a month of testimony and 27 hours of jury deliberation focused on the culpability of the outside helpers. Kiernan and Wade got a break when the panel recommended a mercy sentence of life in prison.

The escapees got no such pity. On June 11, 1942, Riordan followed McGale to the hereafter in the execution chamber at Sing Sing.

They never made it out of the joint.

For years Wade pressed appeals, claiming his confession was coerced during a beating that included 1,400 separate blows. A judge finally agreed in 1958, and he was freed after 17 years. Riordan was paroled a few years later.

At 6:45 a.m. on April 23, the two lawmen who died in the bloody Sing Sing jailbreak all those years ago will be remembered there with a 21-gun salute and the playing of Taps.

Retired Police Officer

April 12, 2015

Create an account for more options, or use this form to leave a Reflection now.