Workam's speciality, however, was killing. In fact, the nickname "Bug" arose out of the sheer admiration of his fellow hoodlums who marvelled at how many murder contracts he had completed. In the span of his short career he was believed to have killed more than 20 people, and was a staff hitman for Lepke Buchalter, often working with the gang of killers known as Murder, Inc.
He was also considered high ranking enough to sit in the counsels of the senior mob leadership, which was highly unusual for someone whose chosen work was assassinating fellow mobsters. So respected, in fact, that his son Chuck Workman, in his highly entertaining book From Murder Incorporated to the PGA Tour : The Remarkable, Untold Story of Charlie the Bug Workman & His Son PGA Pro Chuck Workman, tells the story of a secret party in suburban New Jersey, soon after Workman's final release from prison, where he was said to have been feted by the reigning leadership of organized crime at a secret dinner. Mob luminaries in attendance included, Carlos Marcello, Frank Costello, Gyp de Carlo, Joe Colombo, and Tommy "Three Fingers" Lucchese.
Unlike many of his peers, Workman was said to have carried himself with dignity more befitting the head of a bank than someone whose job description it was to kill people.
Burton Turkus, aka Mr. Arsenic, the Kings County Assistant District Attorney who as a mob prosecutor would ultimately put seven Murder, Inc. assassins in the electric chair, describes his first meeting with Workman where he "fooled you completely . . . he looked like anything but a killer."
In 1935 Workman along with fellow Lepke staff gunman and Murder, Inc. luminary, Mendy Weiss, was given the task of eliminating mob kingpin (and supreme loudmouth) Dutch Schultz by the syndicate's ruling commision, led by the likes of Lepke Buchalter, Frank Costello, Lucky Luciano, Abner "Longie" Zwillman, Meyer Lansky, Albert "The Lord High Executioner" Anastasia and fellow "Bug", Ben "Bugsy" Siegel.
The story told most often of the decision behind ordering the hit was that Schultz, fed up with being harassed by Thomas Dewey, the recently appointed Manhattan Special Prosecutor and scourge of all racketeers, had presented the leadership with the idea of eliminating the gangbusting prosecutor. According to Turkus, the organization went as far as sending Anastassia disguised as a father walking his baby in a carriage to stake out Dewey at his Manhattan apartment and take note of his daily movements. The idea was abandoned with the group fearing it would bring "too much heat" on them. In hindsight, one wonders whether Lepke who was sent to the electric chair in 1944 and Luciano who would serve many years in one of the harshest prisons in America (Clinton/Dannemora) may have lived to regret this decision.
Schultz in rejecting the leadership's decision, went "rogue," threatening to kill Dewey anyway. With that he signed his death warrant.
On October 3, 1935 Workman and Mendy Weiss strolled into Schultz's headquarters, the Palace Chop House in Newark with shotgun and tommy gun in hand and eliminated Schultz, along with Schultz employees, Otto "Abbadabba" Berman, Abe Landau, Bernard "Lulu" Rosenkrantz.
Much to do was made of the fact that after shooting Schultz, Workman delayed the group's exit by going through the dying man's pockets. So delayed that his accomplice Weiss and their driver, one Seymour "Piggy" Schechter, abandoned Workman at the scene forcing him to make his way back home through the swamps of Northern New Jersey on foot. Outraged by this violation of the hitman code of decency, Workman looked to the syndicate leadership to have Weiss killed. In Weiss's defense he argued that it was his right to leave the scene because they were there only for the assassination and NOT the pilfering of cash from the victims. Weiss was acquitted.
With no witnesses and no leads on the murders, the case went cold for years.
In 1940, as part of the Murder, Inc. investigation, Workman was finally identified as one of the Schultz group's assassins by the mob's two biggest turncoats, Allie Tannenbaum and Abe Reles, and stood trial in New Jersey. Initially Workman, "resplendent in chocolate sport shirt and sky-blue sweater," stood his ground contesting the charges against him. Not too far into the trial Workman stood up and pled "no defense."
His son, Chuck, believed that the reason for changing his plea was that he feared the prosecutor would hold his wife, Catherine, as a material witness while DA Turkus believes it was seeing Abe Reles, Murder, Inc's #1 stool pigeon about to get on the stand that convinced him his defense was doomed. Workman had purportedly "bragged" about the Schultz murder to Reles.
Because he pled guilty Workman avoided the Death Penalty and was given a life sentence. He spent the next 23 years imprisoned in New Jersey where as an inmate he was described as quiet and unassuming" and as a "model" prisoner.
Harry Camisa, who was a prison guard at Trenton State Prison during Workman's time there tells of how respected he was in that inmates never spoke to him unless he "started the conversation." He stuck with a few low level mob types and was never bothered by other inmates. Camissa also described Workman's wife Catherine after having seen her on visiting days as looking like a "classy lady, almost like Katherine Hepburn or Lauren Bacall." Catherine had missed but one or two visitations in over two decades of his incarceration.
Because of both Workman's stature in the mob and because he remained completely silent about their activities during all those years in prison his family were rewarded by being taken care of by a whose who of gangsters, boxers and celebrities, including Rocky Graziano, Longie Zwillman and Frank Costello. As befits the type of "gangster" Workman was, he never did speak publicly about the murders that put him in prison for all those years.
On March 10, 1964, after 23 years Workman was released from prison. The 54 year old walked "silent and staring straight head" into his son's Thunderbird and off he went.