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

ByStephen Ruiz
via the web site 

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

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.

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