Otherwise, Billy Skidmore was a hustler. He ran gambling joints inside the Levee and was a regular visitor to Johnny Torrio's Four Deuces saloon at 2222 South Wabash. In 1917 Skidmore had been indicted with seven others including Chicago Chief of Police Charles Healy for operating a graft connection between police and gamblers. Healy lost his job but neither he nor Skidmore did any jail time. When Anton Cermak took over the Cook County Board, Skidmore entered the junk business and received a lucrative county contract to handle scrap iron. He opened a junkyard at 2840 South Kedzie which became Skidmore's new headquarters. Skidmore worked for Jake "Greasy Thumb" Guzak as a contact man with city hall, the Kelly-Nash machine, and later to the state legislature. He aligned himself with Jake Zuta but still it was understood that Skidmore worked best for himself and made no pretenses that he could be trusted. In the early 1930s, he created a shakedown business where he approached the black policy kings like the Jones Brothers and assured them that for the paltry sum of $250 a week, the syndicate would not interfere in their operations. He would then go to the mob and offer them only half of the money he collected, keeping the rest for himself. By 1938, Skidmore had hundreds of deals in place with pimps, prostitutes, rogue cops and burglars.
Skidmore ran his operation out of his junkyard, the Lawndale Scrap Iron and Metal Company. It was there that Skidmore dispensed the mob's graft to police and politicians and collected protection from pimps and loan sharks who worked the rackets that the mob chose to avoid. Skidmore's other office, when he needed to speak to customers working out in the county, was the personal lair of Herbert Burns, the Chief of Cook County's Highway Patrol. Burns owed Skidmore a small fortune for gambling debts.
However, most of Billy's business was done at the junkyard, and it was here that newspaper reporters watched a Chicago police captain named Tom Harrison visit every Saturday morning for almost a year. Harrison said he went to buy fresh eggs for his family. Federal prosecutors said he owed Skidmore ten thousand dollars for gambling debts.
In 1939 the Cook County Chief of Police, Lester Laird, "declared war" on gambling. Needless to say, reporters from the Chicago Tribune were surprised to find the chief visiting Skidmore at his junkyard/handbook operation the day after his declaration of war. As it turns out, the chief had been calling on Skidmore four to six times a month over a five year period. He was also a frequent visitor to
Skidmore's 260-acre estate in McHenry, Illinois. When confronted by reporters about his visits to the Skidmore place, the chief replied that he had gone to personally harass Skidmore into obeying the law. That same afternoon, reporters followed Laird to the Drake Hotel where he had dinner with Skidmore. When a photographer snapped a picture of the two of them together, Laird leaped up from his table and ran out of the hotel through the kitchen.
He resigned the next day.
On March 20, 1942, Skidmore was found guilty of tax evasion and sentenced to Terre Haute prison for two-and-a-half years, plus $5,000 in penalties. Skidmore's cellmates were Sam Giancana and black policy king Edward Jones. Skidmore convinced Jones to acquaint Giancana with the numbers racket on the mostly black south side. When Giancana was released from prison, he and the remnants of the old 42 Gang, invaded the south side and took over the policy racket, eventually banishing Jones to Mexico.
As for Billy Skidmore, he never saw the light of another free day again. He died of cancer while still in prison in 1943.
Green met Henrichsen at Skidmore's junkyard. He knew that Henrichsen had landed the job with Skidmore through Tubbo Gilbert's influence. In fact, years later Henrichsen's widow swore out a statement that Gilbert had actually ordered Skidmore to give Henrichsen the job.
"He told me," Green recalled, "Tubbo Gilbert and Assistant States Attorney Crowley told me I had a choice of being a defendant or eating steaks at the States Attorney's expense. They said that if I ever got out of line they would indict me for kidnapping Factor and that I could get up there [on the stand] with Touhy and the others."
Green pushed for more information and Henrichsen eventually admitted that he and Eddie Schwabauer had been paid off by John Factor to lie on the witness stand. He said that he went to the Sycamore jail, where Factor was temporarily held after the kidnap trial ended pending a decision on his immigration status, and "I would meet him on the stairs there, me and Eddie Schwabauer, and Factor would pay us."
Green tried for the impossible. "Look, you know Touhy is innocent, I know Touhy's innocent on this thing, now why don't you do right by him and tell the truth about this to a judge?"
Henrichsen laughed it off. "Look, I got a wife and four kids and I got to provide for them, and I'm not going to do nothing that gets on the wrong side of Tubbo [Gilbert]...look, I got a choice here, I mean I could have testified the way I did and eat steaks at the County's expense or I could have been a defendant. They, Tubbo and Crowley and them, they told me real, real clear, they said I would be indicted right along with Roger and those fellows if I didn't testify the way they wanted."