During a 38-year career in law enforcement, James E. O’Grady was a second-generation Irish American police officer and then Chicago’s police superintendent for a year before later serving one term as Cook County sheriff. “Jim was a great street cop and was the first of his kind to be the super intendent,” said former Chicago police Superintendent Phil Cline, now the executive director of the Chicago Police Memorial Foundation. “Superintendent O’Grady would always acknowledge street cops when he encountered them on the street. This earned him a lot of respect from street cops.” Former Chicago police Superintendent James O'Grady. (Chicago Police Department) O’Grady, 96, died of natural causes on Jan. 5, said longtime friend and colleague Neil Sullivan, a former Cook County chief deputy sheriff. O’Grady had been a longtime resident of the Edgebrook neighborhood on the Northwest Side. Born in Chicago, James Edward O’Grady was the son of Irish immigrants. His father, Thomas O’Grady, was a Chicago police sergeant who retired in 1955. Raised in a house near the intersection of Belmont and Kedzie avenues, O’Grady graduated from St. George High School and he later went back to school, getting a bachelor’s degree from DePaul University in the mid-1970s. From 1948 until 1952, O’Grady worked as a florist for the Chicago Park District while seeking to take a police exam. In 1952, he joined the Chicago Police Department, working as a patrolman for eight years. O’Grady was promoted to be a sergeant in 1960, a lieutenant in 1965 and a captain in 1969. In his assignments, O’Grady moved up to be the head of the unit targeting prostitution and the vice control division. He later was the watch commander in the Chicago Avenue district, commander in the Prairie Avenue district — one of the city’s largest — and chief of the 1,300-person criminal investigation division. In 1968, O’Grady was knocked unconscious by a rock thrown during disturbances at the now-demolished Cabrini-Green housing complex. Then, in December 1971, while off-duty, he was shot in the left hip in a Loop alley while chasing a man who had snatched a purse from an elderly woman — an incident that earned him the Chicago Police Department’s Blue Star Award. “He whipped around and shot me, and I returned fire,” O’Grady told the Tribune’s Jack Hurst in 1978. “When I got hit I went down, and I was firing from the ground, and he was shooting at me. He fired four shots. I fired three. The guy that I was with, a sergeant, came up and went into a crouch to shoot, but by that time the guy was 125 to 150 feet away — at rush hour in the Loop. So I said, ‘Don’t fire.’ It wasn’t because I didn’t want him to shoot that sonofab—- — but sure as God made little apples, he would’ve accidentally shot somebody else.” O’Grady was appointed police superintendent in April 1978. In that short tenure, he promoted the first Black woman to the rank of sergeant, promised more meaningful use of women on the force and pledged more diversity in hiring. At the outset, he drew positive marks for getting tough on police corruption. “The toughest problem I face is getting all the people of the city to believe that the police are really serving them, that we’re doing our best to bring them good police service, that the people of this department have the welfare of citizens at heart,” O’Grady told the Tribune in 1978. “If I could change any one thing, that’s what I’d like to do.” Sullivan said O’Grady was always a police officer first. “He was good at what his life’s (work) was, and that was being a police officer — not as a command officer, but as a police officer,” Sullivan said. “When he put on his command hat, he was always very much for the rank and file, for the men and women who worked in the department to make sure that everything he did was in their best interests, to help them and make sure that they went home to their families at night.” As superintendent, O’Grady was criticized by the Better Government Association for not sufficiently curbing illegal spying by police officers on citizens and political organizations. He also came under fire after news reports that police officers were strip-searching female motorists stopped for minor traffic offenses. Although O’Grady halted strip searches in response to news articles, he admitted that police had not exactly moved expeditiously in looking into the issue, acknowledging that police had investigated complaints about improper strip searches for at least 10 months. After just a year and eight days as police superintendent, O’Grady resigned and was demoted to captain as newly sworn-in Mayor Jane Byrne had vowed to fire him, alleging that he had politicized the Police Department. Soon afterward, O’Grady went on a leave of absence from the Chicago Police Department and took a job as Cook County Sheriff Richard Elrod’s undersheriff. Two years later, in a surprise move, then-police Superintendent Richard Brzeczek brought O’Grady back as first deputy superintendent. Byrne later reversed her opinion of O’Grady, explaining that she had gotten an incorrect impression of him from newspaper articles. Asked in 1981 if he was still angry with Byrne and could work under her, O’Grady told reporters that “life is too short to have any hard feelings for anybody.” In April 1983, O’Grady became acting police superintendent upon Brzeczek’s resignation, serving in that role for more than three months. After that, he reverted to being first deputy superintendent. O’Grady left the force in 1984 to take over Special Operations Associates, a Southwest Side detective agency. The following year, he changed parties and decided to run in 1986 as a Republican against his former boss, Elrod, who had been sheriff for 16 years. “It’s more important to be loyal to the profession of policing than what Elrod perceives as loyal to him,” O’Grady told the Tribune’s Bruce Dold in 1986. In an upset, O’Grady defeated Elrod — making him the first Republican to win county office in a decade — and he pledged to clean up an office tainted by corruption. However, during O’Grady’s single term as sheriff, his undersheriff, James Dvorak, was alleged to have demanded campaign contributions from subordinates. A Tribune investigation in 1989 showed that despite campaigning for sheriff on a pledge to end political fundraising in office, O’Grady had collected more than $350,000 from jail guards, sheriff’s police and other employees. Amid allegations of corruption and political favoritism in jobs and promotions, O’Grady was soundly defeated for reelection in 1990 by Democrat Michael Sheahan both in Chicago and in then-Republican strongholds in suburban Cook County. The race was bitter and occasionally violent. A Cook County correctional officer who supported Sheahan was shot three times and critically wounded outside a South Side tavern. The Sheahan campaign said the officer was hanging Sheahan signs, but O’Grady said the officer was tearing down O’Grady signs. Three men, including a correctional officer supporting O’Grady, were arrested in the incident. In 1993, Dvorak pleaded guilty to federal bribery and other charges. He was sentenced the following year to 41 months in prison while a massive ghost-payrolling and hiring scandal in the sheriff’s office netted Dvorak an additional 40 months behind bars when he was sentenced in 1996. Though O’Grady was never charged with a crime, a lengthy federal investigation into his term produced more than a dozen guilty pleas by associates and uncovered rampant corruption, including a hiring scandal that gave jobs, badges and the legal right to carry handguns to at least 455 unqualified applicants for jobs as deputy sheriffs and correctional officers in exchange for favors. Outside of work, O’Grady was a member of Ridgemoor Country Club in Harwood Heights. He also enjoyed playing handball, softball and golf. O’Grady’s wife of 67 years, Joan, died in 2022. He is survived by two daughters, Margaret “Peggy” Parker and Joanne Dunderdale; three sons, James, Michael and John; nine grandchildren; and seven great-grandchildren. Services were held. Bob Goldsborough is a freelance reporter. ...read more read less