Editor’s Note: The passage of time has not lessened the evils of political partisanship which inevitably impacts law enforcement and the administration of justice in the Cook County Sheriff’s Office and Police Department. With a few notable exceptions, the Sheriffs who span the full gamut of 160 years of Cook County history have served their political masters and themselves better than the voting electorate. The historic struggle between reform, political machinery, and organized crime is a recurring theme when one reviews the record of the Cook County Sheriff’s Office and particularly the Police Department. The scandal, the infamy, and the corruption associated with the administration of this office down through the years is the subject of a continuing IPSN four-part focus report. In Part II, we examine a jail house scandal from the 1920s, illustrating to the continuous and historic problems plaguing the office of Cook County Sheriff since its inception.

Part Two: The Stench From the Jail

As much as things may appear to change in this world, some things, like death, taxes, and the mess down at the Cook County Jail (now known as the Department of Corrections) never change. The problems of overcrowding, prisoner escapes, and gang control of the tiers, contribute to a beleagured morale among correctional officers which in turn fosters complacency, and corruption. The byproduct of a morally bankrupt correctional system is of course political scandal, and when the scandal occurs, inevitably the final responsibility rests with the incumbent Cook County Sheriff, whomever that may be at the time.

Stupidity, avarice, and political wheeler-dealing characterized the administration of the Cook County Sheriff’s office in the years following the formal organization of the Highway Patrol (the Cook County Police Department, as it is now known) in April 1922.

Coincidental with the birth of the Highway Police that year was the election of the oafish Peter M. Hoffman as Cook County’s 35th Sheriff since 1831. Hoffman is unique in Cook County annals. Not even the Machiavellian erstwhile jailbird Jimmy Dvorak (undersheriff of Cook County 1986-1990), can match Hoffman’s unparalleled accomplishment as the only Sheriff who served prison time while still occupying office.

The good Sheriff Hoffman entered office in 1922 “well qualified” by previous standards – which is to say – there were no standards. This former grocery store clerk was elected to the Cook County Board of Commissioners in 1898, and served in this capacity until 1904 when he was swept into the Coroner’s office. Hoffman supervised the Morgue continuously until 1922 when he was elected Sheriff on a “reform” platform.

Cook County Jail, then located at 440 N. Dearborn St., was termed the “worst in the nation,” when Hoffman vowed to “clean up” after his two predecessors, John E. Traeger, and Charles Peters had failed so miserably. The Traeger and Peters regimes were compromised by repeated jail escapes, which prompted the hiring of one Warden Wesley Westbrook, a former Deputy Superintendent in the Chicago Police Department who had the reputation of being a no-nonsense, straight arrow. Westbrook was hired by Peters, and retained by Hoffman after various reform groups sang his praises at election time.

Behind the barred portals and stewing in the locked darkness of a jail cell in the old County Jail, resided the infamous Frankie Lake, and Terry Druggan, Prohibition-era bootleggers in charge of the Valley Gang – West Side liquor distributors who were bigger than Al Capone in the early years of the 1920s before the”Big Guy” consolidated the Chicago rackets and absorbed their holdings into his own empire.

The jailed beer kings cut a deal with the supposedly unimpeachable Westbrook calling for delivery of $2,000 a month – payments were made by 20th Ward political boss Morris Eller on the first and 16th of the month – in return for the granting of special “favors” to the boys, which included periodic furloughs from the County Jail in order for them to attend to their bootlegging empire; conjugal visits from girlfriends; private rooms with their own baths; and deluxe accommodations from the jail house staff.

When a newspaper reporter dropped by the jail one afternoon to interview the gangsters, a secretary informed him they were not “available” at the moment. “Mr. Druggan and Mr. Lake are out right now…an appointment downtown,” she said. “They’ll return after dinner.” (It kind of reminds you of Sheriff Michael Sheahan’s generous I-Bond procedures, does it not?)

The system of payoffs finally bubbled to the surface in September 1925. Among other things, Terry Druggan revealed to members of an astonished federal grand jury just how accommodating the Sheriff and the Warden could be at times.

Q – Now three times you were out visiting the dentist. What else did you do besides visit the dentist?

Druggan – I used to walk. I used to walk from Grand Avenue east all the way up around the lake every day to get my health back. I used to take them long walks. Regularly, yes sir.

Sheriff Hoffman and Warden Westbrook were eventually charged with contempt of court after their neat little scandal hit the front pages. Federal Judge James H. Wilkerson sentenced the bumbling Hoffman to 30 days in his own jail and ordered him to pay a $2,500 fine. The good Sheriff shrugged his shoulders and wondered aloud: “I don’t know what all the fuss is about. I was only accommodation’ the boys.” Westbrook received four months – his wife offered the opinion that he “must have been insane” as off to jail he marched.

Sheriff Peter Hoffman served his time…then completed his scandal-ridden term of office in 1926. He later found gainful employment in the forest preserve construction service, and died a happy, contented man at the ripe old age of 85.

If Cook County voters had learned anything at all from the Hoffman-Westbrook imbroglio, it was that corruption would likely prevail as long the position of Sheriff remained an elective office controlled by Chicago and Cook County dealmakers and slatemakers.

Sheriff Charles E. Graydon replaced Paddy Carr, an old-line politico who was elected Sheriff in 1926. However, Carr died in office before collecting his first paycheck forcing a (then) Republican administration in Chicago to anoint a worthy successor. Charley Graydon’s “stick man” happened to be Chicago’s cartoonish mayor, William Hale Thompson, a syndicate lackey who pulled the wires for Graydon’s immediate appointment.

The thoroughly corrupted regime of Mr. Graydon witnessed unparalleled expansion of slot machine gambling, vice, and bootlegging outside Chicago which followed the slow but constant population shift from city to suburb. Roger Touhy, boss of the Northwest Suburban rackets, installed his trusted henchman Matt Kolb as a highway policeman under Graydon’s administration, and business flourished like never before. Wide open as usual.

If an unfavorable newspaper story appeared in one of the Chicago dailies about slot machines running wild throughout the northwest part of the county, there would be a telephone call made to Cook County Highway Patrolman Kolb, and he would then instructed the tavern and saloon people to tuck the devices safely out of sight until the high sign was given by an upper-echelon figure named Lieutenant James Meyering. “It was entirely up to the Sheriff whether the slot machines would run or not,” the rugged Irish rascal Roger Touhy exclaimed.

The Touhy-Kolb alliance elected Jim Meyering’s brother William, a decorated World War I hero, as Cook County Sheriff in 1930. Elected on the Democratic ticket, Meyering spoke the truth when he said: “I am not a reformer. I do not intend to become one.” Now there’s a shot – a “pol” telling it as it is.

Real power was always wielded by Kolb of course, who was shot in the head six times at his Morton Grove tavern on October 17, 1931 by a team of assassins sent out by Al Capone after Kolb refused to relinquish his holdings to Capone’s sidekick Jake Guzik. The murderers were never identified, of course and as spoken previously, as much as things change in this world they remain the same.

After the hit, Roger Touhy’s influence over the suburban rackets and the sprawling roadhouse district along Dempster Street waned as the Capone syndicate became the exclusive supplier of slots, craps, booze, and broads which the Sheriff seemed powerless – or unwilling to control.

The repeal of theVolstead Act in 1933 ended the wild and woolly Prohibition era and ushered in a 4-year-period of relative stability and calm in the Sheriff’s Office. Democrat John Toman, a Chicago ward boss whose son Andrew served as Cook County Coroner under Mayor Richard Daley I in the 1960s, conducted a surprisingly scandal-free administration as Sheriff spanning the years 1934-1938. No small feat in Crook County. Toman demonstrated that it was indeed possible – even desirable – to implement reforms with minimal outside political interference. Toman modernized the Highway Patrol Police by re- designing the patrol cars, and requiring his officers to be trained by Red Cross instructors instead of just precinct captains.

Hard-core incarcerated criminals were segregated from first offenders, and his fair and compassionate handling of the inmates at the recently opened jail facility at 26th and California, was praised by the Chicago Crime Commission and other civic agencies whose endorsement he received when he announced his candidacy for County Treasurer in 1938. It was unfortunate for the voters of Cook County that a dedicated and refreshing public servant like Toman was not permitted to stand for re-election as Sheriff because of the mandate contained within the State Constitution at the time. Tragic – because a clown prince of Chicago politics waited in the wings to further embarrass the reputations of the hard- working men who wore the khakis, and tarnish the Cook County Police star forever more.