Monk Eastman, according to Herbert Asbury’s 1927 book, was:
...as brave a thug as ever shot an enemy in the back or blackjacked a voter at the polls...So far as looks were concerned, and actions, too, for that matter, Eastman was a true moving picture gangster. He began life with a bullet-shaped head, and during his turbulent career acquired a broken nose and a pair of cauliflower ears, which were not calculated to increase his beauty. He had heavily veined, sagging jowls, and a short, bull neck, plentifully scarred with battle marks, as were his cheeks. He seemed always to need a hair cut, and he accentuated his ferocious and unusual appearance by affecting a derby hat several sizes too small, which perched precariously atop his shock of bristly, unruly hair. (Asbury, The Gangs of New York, page 255.)
His real name was Edward Osterman. Born in 1873, after the Dead Rabbits gang no longer existed, he was regarded as “king” of the New York gangsters during the late 1890s and early 1900s. He was chief of the Eastman gang which terrorized New York between the Bowery and 14th Street, until Monk was sentenced to Sing Sing for "highway robbery" and felonious assault in 1904. He was never a powerful force in New York's gangs again, even though he only served half of his ten-year sentence.
When Monk went down, his gang split into three parts which eventually turned on each other. Johnny (Jack) Sirocco took over one remnant, but according to Asbury's account, Sirocco spent more of his time on legitimate business interests than on gang leadership (even though he took part in a 1914 incident at 21-25 St. Mark's Place in the East Village).
Sirocco, whose appearance was almost as awe-inspiring as that of Monk Eastman himself - he invariably wore a plaid cap drawn down over his eyes and seldom shaved - operated a prosperous gin-mill in the Bowery which became a favorite haunt of the gangsters after some of the Chinatown dives had been closed. (Gangs, pages 302-303.)
When WWI broke out, Monk enlisted in the infantry (as William Delaney) where he served with courage and distinction. He was, in fact, considered a hero by many for the bravery he demonstrated during the war.
Returning soldiers, passing by New York’s Public Library, were honored by New Yorkers. Was Monk Eastman somewhere in this returning group of heroes?
As it happened, however, Monk appears to have quickly slipped back into his old ways upon leaving the military and was gunned down in 1920. His WWI pals paid for his funeral. He was buried, with full military honors, at Brooklyn’s Cypress Hill Cemetery.