Editor’s Note: As much as things may appear to change within the mysterious, darkly lit corridors of Cook County government, when all is said and done, nothing really changes. 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 better than the voting electorate. The historic struggle between reform and the machine, and reform and organized crime is a recurring theme when one reviews the record of the Cook County Police Department. The scandal, the infamy, and the corruption associated with the administration of this office down through the years is the subject of an IPSN four-part focus report that first appeared in our newspaper three years ago.

Part One: The Early Years

There has been a Cook County Sheriff almost as long as there has been a Cook County. John Kinzie, one of the earliest white settlers to arrive on the banks of Lake Michigan when the region was a sandy marsh inhabited by hostile Pottawatamie Indians, was Cook County’s first. Kinzie earned a considerable fortune in the fur trading business and was elected Sheriff in 1831 at a time when the lonely military outpost on the fringe of the Western frontier was fast becoming a modern city. The City of Chicago.

Kinzie, like so many of the men who were to follow in his footsteps, was elected on the basis of his political and financial standing in the community. Professional politicians have occupied this office ever since. The one notable exception of course was ex-Chicago Police Superintendent James O’Grady and he immediately proceeded to outdo the political pros and may yet prove to be the most corrupt Sheriff of them all.

Until 1882, the Sheriff served a two year term, and by statute could not stand for re-election. The primary responsibility of the office holder in those early days was to administer the city jail – or Bridewell – as it was commonly referred to in 19th Century parlance, and to oversee the bonding-out of felons and misdemeanants in the local courts.

Cook County’s ever-infamous crime syndicates began to evolve after the Civil War, the downtown gambling bosses and the powerful ward leaders who protected their flourishing faro dens, roulette games, and city-wide bunko operations, found it expedient to their long-term prosperity to elect a “friendly” Sheriff – one who might serve a useful purpose when a gambling den was infrequently “pulled” (or raided) by Chicago Police of character.

Cooperation with the Cook County Sheriff meant that a well-heeled client, a rich businessman or out of town salesman who had spent his money lavishly in one of the politically “connected” gambling dens for example, could avoid the embarrassment of incarceration and pay only a nominal fine if the Magistrate was willing (which was usually the case). Bond money was usually split four ways: the arresting Police officer; the Magistrate; the Sheriff; and the gambling den each received a cut. Even then it was a million-dollar racket that reached its peak in the mid-1880s – the heyday of downtown “parlor” gambling in Chicago when Randolph Street had the feel of the present Vegas strip.

Bail bonds were of course provided by agents of the Sheriff who worked in connivance with the court and the police. If the arrestee decided to skip town it was of little immediate concern to the mob’s people. The gambler was more than likely to return to the “action” once the heat wore off. The forfeiture of bonds were widespread in Cook County, and conveniently ignored by the Sheriff as long as he had the word of the house that their man was “good.” If the offender fled the county, it was of little concern because every one still came out ahead On the other hand, rival gamblers who operated outside the protection of the syndicate people were likely to face swift prosecution and the full punishment allowed by law.

The most notorious abuse of power occurred under the administration of Chicago Police Chief William J. McGarigle (1881-1882), a college-educated man who masqueraded as a reformer. McGarigle steered his raiding parties away from the gambling dens owned by Michael C. McDonald, a wealthy and powerful gamesman who controlled the internal mechanisms of the Democratic Central Committee in the last quarter of the 19th Century. McDonald was a king-maker who drew up the blueprints for the Hinky Dink Kennas, Jake Arveys, and Richard Daleys who were to follow. In 1882, McDonald had it in his mind that he could elect his friend McGarigle to the post of Sheriff, despite the word of caution coming from the mayor, Carter H. Harrison I.

McDonald was quite simply the most powerful man in Chicago and he slated McGarigle on the Democratic ballot and didn’t care a wit for what the mayor had to say. It was a power move designed to protect the bail bonding rackets, now threatened by a Republican reform candidate. However in a stunning upset, the Republican, Seth Hanchett won, and thus became the County’s first 4-year Sheriff.

Hanchett was succeeded by the bumbling Canute R. Matson in 1886. Matson was a close friend of McGarigle, who by this time, had been placed in charge of the disease-infested Cook County Hospital by McDonald, who dictated his appointment to the members of the Cook County Board which he also happened to control. As Hospital Warden, McGarigle ordered expensive caviar and fine wines for himself from wholesale suppliers and paid for them with taxpayer money while the wretched inmates of the institution were deprived of clean linen and forced to eat rancid meats and stale bread.

A sensational newspaper expose revealed the grafting of McGarigle and a dozen of his cohorts serving on the County Board in 1887. They were indicted for massive fraud and corruption. The “Boodler” case had only one modern parallel – and that had occurred in the 1870 when Mayor William Marcy Tweed and his plundering Tweed Ring raped the New York City treasury of millions of dollars. Former Chief McGarigle, considered the “best and brightest” of his generation at the time he was slated for Sheriff by McDonald, was indicted and jailed in the County lock-up in 1887. Hours before the first verdicts were handed down, McGarigle requested from Matson a two-hour “furlough” from the jail in order to visit his wife and children in the Lakeview area of Chicago.

Sheriff Matson personally escorted McGarigle to his residence and waited patiently in the front parlor for his prisoner to take a bath, change into fresh clothes and return with him to the jail. After an hour had passed Matson grew suspicious and asked the wife when her husband might be coming down from his upstairs bedroom. “I do no know where William went to,” Mrs. McGarigle sheepishly replied. The witless Sheriff raced upstairs and discovered to his horror that the bathroom window was wide open. McGarigle had lowered himself into the backyard and had vanished into the city.

As it turned out the former Police Chief had tricked Matson into becoming an unwitting accomplice in his well-planned, and daring escape. McGarigle would continue his evening absolutions in Canadian waters after hooking up with a Lake Michigan steamer to convey him northward through the Straits of Mackinac toward freedom. He settled in picturesque Banff, located in the Northern Territories, and would establish residence there for two more years until he was at last persuaded to return to Chicago and accept a suspended sentence from an obliging judge. Sheriff Matson drifted into political obscurity thereafter. McGarigle, meanwhile, purchased a North Side saloon where he would regale his customers with tales of an escape that might easily be mistaken for an amusing bit of folklore if not for the fact that every word of the story was true.

Until 1922 there was no Cook County Sheriff’s Police Department per se, and the administration of the jail (then located in back of the old Criminal Courts Building on Chicago’s Hubbard Street), and the upkeep of the inmate population continued to provide numerous grafting opportunities for each incoming Cook County Sheriff.

One way a Sheriff could supplement his salary was to pocket the difference between what it actually cost him to feed the inmate population and the 21 cents (per head) paid to him out of the Cook County treasury. How much it actually cost the Sheriff to provide daily sustenance to a prisoner was a matter of guess work. But under the regime of Sheriff Chris Strassheim (1906-1910), it was reliably reported that it cost only 6 cents a day to feed a single prisoner in 1907. Strassheim collected as his own reward, the fees and emoluments that should have rightfully been deposited in the Cook County Treasury, prompting the Chicago Tribune to bitterly complain that: “One sheriff after another has made money out of feeding the inmates of the jail, but the practice is illegal. The law officers of the county may see the propriety of bringing suit against the sheriff to recover the amount now due from him.” To our knowledge no such law suit was ever filed.

Sheriff Charles W. Peters was the incumbent office holder when the most celebrated jail escape of them all occurred on that fatal day of December 19, 1921. “Terrible” Tommy O’Connor, a convicted cop killer, scaled the walls of the jail just three days before he was scheduled to hang for the murder of Chicago Detective Sergeant Patrick “Paddy” O’Neill, who was killed in the cross-fire of a police shoot-out nine months earlier.

The Chicago Police had gone to great lengths to apprehend the fugitive O’Connor, who had committed a string of armed robberies dating back to 1910. Time and time again, pint-sized Tommy (who bore an amazing resemblance to First Ward Alderman Michael “Hinky Dink” Kenna in his younger, more fertile days), eluded their grasp until a switch foreman on the Chicago-Great Western passenger line subdued the little mug outside of Minneapolis on July 25, 1921. Fifty of Chicago’s finest raced to the Twin Cities to bring O’Connor back to Chicago. No-one was taking any chances this time.

After being sentenced to death by Judge Kickham Scanlan the following October, Terrible Tommy’s execution seemed almost pro forma. “Tommy O’Connor will never hang!” That was the word on the streets, and as the date of execution crept ever closer Sheriff Peters and his men grew edgy and tense.

The condemned man and four criminal associates overpowered guard David Straus on the morning of December 19. An obliging prison cook received a pistol from an O’Connor accomplice outside the walls and had smuggled it into Tommy’s death row cell. The rest as they say, is history. O’Connor commandeered a get away car and disappeared into the County. There was no Cook County Highway Patrol (as they were to be called for a period of our history) in the suburban areas to stop him; just miles and miles of unpatrolled farm land and rough gravel roads. The rotting wooden gallows reserved for O’Connor were not dismantled until 1977, by which time it was apparent that Tommy would not be coming back.

Commenting on the sorry conditions at the Cook County Jail on Hubbard Street, (then) Chicago Police Chief Charles Fitzmorris remarked: “Stone walls do not a prison make. That might refer to our county jail. Conditions there are absolutely appalling. If the people knew how bad conditions were they would not go to sleep at night, or they would wake up screaming.”

(Shades of 1994).

The attending scandal, and the absence of adequate policing for the 1,600 square miles of suburban expanse in Cook County underscored the crying need for the creation of a Highway Patrol Police. The frequency of armed holdups on the rural highways was becoming more alarming to the law abiding citizens of the metropolitan region who were venturing further and further outside the city limits, or as far as their Model-T Fords could carry them on Cook County’s rough, uneven suburban roads. It was common practice in those days for robbers to hide in the ditch while a female accomplice would lure the victim into a trap by lying across the road, feigning injury. The crime victim often found himself marooned on a deserted country road, having been relieved of his cash, his valuables, and his automobile. Hard to imagine, but one such country road where these kinds of scams were perpetrated in the early 1920s is today bustling Dempster Street in Skokie.

Until the Cook County Highway Patrol Police Department was formally organized on March 1, 1922, there were only 12 police officers assigned to guard approximately 235 miles of paved roads. The dozen or so motor cycle cops were assigned by George A.Quinlan, Superintendent of Highways, but they were untrained in the prevention and detection of crime and hopelessly understaffed. Their effectiveness was linked to the cooperation they received from local police agencies in the towns and villages comprising suburban Cook County which meant that auto thieves, hold-up men, and other roving criminals were virtually immune from arrest provided they remained well outside local city limits.

The first 70 Cook County Police Officers (the Highway Patrol Police) were on the job in April 1922. They donned khaki uniforms and leather puttees crafted along the lines of a U.S. Army uniform. The men were strategically stationed in the North, South, and West ends of the County. Station I was originally located at Dempster St. and Waukegan Road (later moved to Milwaukee Avenue in Niles), where most of the trouble was occurring, and on the South end at 147th and Western Avenues. The slogan adopted by the new policing agency was “Safety First.” It remained to be seen.