How the 'First Real New York Gangster' Turned Guardsman Helped End World War I

As Monk Eastman lay in a field hospital, he learned his infantry division was preparing to breach the Hindenburg Line -- the Germans' last line of defense on the Western Front during World War I. Despite being sidelined with leg injuries and the victim of a gas attack, Eastman didn't come this far to be a bystander.

Half-naked and with bare feet, Eastman fled the hospital under the cover of night to join his company. He helped the Allies penetrate the Hindenburg Line on Sept. 29, 1918, six weeks before an armistice agreement was signed.

It wasn't surprising that Eastman did not follow doctor's orders. Following rules was not in his DNA, for Eastman had been a gangster before he enlisted in the New York National Guard in 1917.

Born Edward Osterman, Edward "Monk" Eastman led a collection of criminals that, at one point, numbered nearly 1,200. The infamous Eastman Gang's illegal enterprises including larceny, running brothels, dealing opium (Eastman became an opium addict) and rigging elections for Tammany Hall.

Eastman -- dubbed the "first real New York gangster" -- served several prison sentences, including at Sing Sing. After he was convicted for stealing silver, Eastman served about three years in another prison and was released in October 1917. By that time, his gang had disbanded, and the United States was embroiled in WWI.

Keeping his past secret, Eastman -- in his early 40s at the time -- enlisted under the alias William Delaney. When Army medical examiners in Brooklyn saw his scar-covered torso, misshapen ears and a nose that had taken its share of punishment, they wondered what had happened.

"Oh, just a lot of little private wars around New York," Eastman told them, according to a story on warhistoryonline.com.

Eastman saw no reason to elaborate, and the doctors -- finding that answer sufficient or perhaps deciding they didn't want to know more -- didn't inquire further. Eastman passed his physical and joined the 106th Regiment of the 27th Infantry Division of the New York National Guard.

The division became known as O'Ryan's Roughnecks, named after its commander, Maj. Gen. Frank O'Ryan. Unaware of Eastman's background, others in the unit teased him. They called him "Pop," but it didn't take very long for Eastman to gain the Roughnecks' respect during training at Camp Wadsworth in South Carolina.

"The old man could outrun anybody in the unit," according to this story from 2016. "When Eastman hit a bayoneting dummy, he nearly tore it in half. Delaney's secret came out and the taunting ended: Pop was Monk Eastman, the infamous Bowery desperado."

The son of a Civil War veteran, Eastman seemed a natural for the military despite his advanced age and checkered past. He sometimes led nighttime missions into no man's land -- that area separating the front lines of opposing armies.

Stories emerged of Eastman rescuing troops, eliminating machine gun nests and continuing fighting after being shot in the hand. When German fire pinned his regiment at Vierstraat Ridge in Belgium, Eastman hurled bombs at the enemy.

"The German gunners caught sight of him," The New York Tribune reported. "They could not depress their gun sufficiently to hit him and Monk crawled forward and blew them up."

Eastman's bravery led to his hospitalization, during which he learned about the plan to break through the Hindenburg Line -- a defensive barrier that the Germans had constructed in 1917 and so far had been impregnable.

Eastman and the rest of the 106th led the initial charge on a tunnel, where German reinforcements were positioned nearby. In the process, the regiment helped establish a foothold for Allied forces, despite coming under heavy attack.

When the unit retreated to the rear after the position was secured, Eastman asked to stay behind. He wanted to be a stretcher bearer, so he could help carry wounded soldiers to safety.

After a 56-hour engagement, the Allies broke through the Hindenburg Line.

Despite his accomplishments, Eastman apparently was not especially impressed with his military service, once boasting: "There were lots of dance halls in the Bowery tougher than that so-called 'Great War' of theirs."

In May 1919, New York Gov. Al Smith pardoned Eastman. Given a second chance, Eastman didn't take advantage of it. He went to work for a mob boss and died on Dec. 26, 1920, when he was shot to death by a corrupt Prohibition agent.

-- Stephen Ruiz can be reached at stephen.ruiz@military.com.

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