HOW I MET DICK CAIN
On a cold Tuesday evening in November 1962, I was sitting in a suite in the LaSalle Hotel in Chicago talking with Dorothy Ogilvie, wife of the Republican candidate for Sheriff of Cook County. There was a crowd of about a dozen sitting or standing in the various attached rooms. We were awaiting the arrival of Candidate Ogilvie on this election night. Dick had asked me to be his reform chief of the Cook County Sheriff's Police (CCSPD) if he was elected sheriff and I who at that time was a lieutenant and Acting Director of Training in the Chicago Police Department had accepted.
 
Richard B. Ogilvie had been born in Kansas City, Missouri, in 1923. During World War II he was wounded in the face while serving in an attack tank company under the command of General George Patton. After the war he entered politics as a Young Republican. In 1958, he was appointed  by U.S. Attorney General William Rogers as Chief of the Midwestern unit of the "Special Group on Organized Crime." During his service as a federal prosecutor Ogilvie indicted and convicted Chicago Syndicate Chieftain Tony Accardo in federal court on charges of income tax fraud. The press praised him highly as a man of great integrity and as an incorruptible crime fighter. On this stain-free reputation he ran for the office of Sheriff of Cook County.
 
In his campaign talks Ogilvie promised to relentlessly battle the crime syndicate and put them out of action in Cook County. He said he would personally select his staff to insure their integrity. He kept his word to a fault.
The door from the corridor opened and the thirty-nine-year-old Ogilvie entered the room. He was wearing an overcoat, dark suit, white shirt and tie. Behind him was a short young man wearing horn-rimmed glasses. A third man followed them into the suite. All three were wearing top coats and dark suits with white shirts and ties. All were hatless. The two men with Ogilvie carefully eyed the guests. The short man was Cain who was thirty-one-years old. The other was one of Cain's aides.
As the three took off their outer coats, I asked Dorothy who the two men were with her husband. She gave me a curious look and said, "Don't you know them. They are Dick Cain and his partner. I immediately recognized the name Dick Cain. Even though Cain and I had served at the same time on the Chicago Police Department, my knowledge of Cain was limited to what I had read over the years in the Chicago newspapers. Cain had appeared in the press several times, always in a negative light. From his newspaper reputation I considered him a rogue cop, at best. And a crooked cop at worst. He stood for, all of the things I was against in law enforcement. A discredit to his badge and possibly a criminal.
I had read that Cain had been involved in a prostitution raid on the South Side in which the 68-year-old madam named Grace Van Scoyk charged that $30,000 of her money was stolen from her, that Cain and his partner had shot and killed a man who had been involved in homosexual shakedowns in the washrooms of the Greyhound Bus Terminal in the Loop, that Cain and his partner while on vacation furlough from their jobs on the CPD burglary squad had been working for State's Attorney's Chief Investigator Paul Newey and had been caught attempting to wiretap the office of the City of Chicago Commissioner of Investigations.
 
I had not been on the inside of the Chicago Police gossip chain and I did not know that Cain was considered by his fellow officers as worse than the newspapers had pictured him.
 
That election night when Ogilvie came over to talk with Dorothy I asked him if I could see him in private. He agreed and the two of us walked into an adjacent bedroom and closed the door. We each sat on the edge of a twin bed facing each other.
Dick said, "Well?" I asked Dick why he had come in with Cain. Dick said that Cain was providing security for him and if elected Cain was going to work directly for Ogilvie in charge of a special unit to "take down" the Outfit.
 
This information came as a great surprise. I could not understand why Ogilvie with his extraordinary reputation for honesty and integrity would want to hook up with someone like Cain. I bluntly said as much to Ogilvie. Ogilvie told me that he had heard all of this negative "stuff" about Cain before but that he had checked Cain out with people he trusted and found Cain to be "OK." I protested that Cain was someone who engaged in disreputable methods. "Right," Ogilvie replied. He said that after he had offered me the position of Chief of the Cook County Sheriff's Police he believed I would build an honorable police force but he "needed someone to cover his back." Ogilvie said that Cain was used to working in alleys and would afford Ogilvie protection from any dirty dealings that the Outfit might use to discredit or harm him when the sheriff's police led by me began to bear down on the Mob. He said he had decided to divide the responsibility for dealing with the Chicago Outfit between me and Cain. Ogilvie said that I was to attack all vice and gambling operations run by the Mob and the lower echelon Mob members. Cain would go after the bosses and higher ups in the Syndicate.
 
I listened silently to what seemed like an explanation that had been created after the fact. The problem was I did not know what the "fact" was.
 
We both rose to join the others in the living room and watch the election returns. As the night turned into the early morning the television reported that Ogilvie had edged out the incorruptible Roswell Spencer, formerly a squad leader in the FBI, in a close race for the office of sheriff.
 
Would that the success in the election was a sign of four good years for Sheriff Ogilvie. Unfortunately, my forebodings turned out to be more than accurate and only two years ahead Cain was to almost bring down the new sheriff.