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James E. O'Grady
Sheriff of Cook County, Illinois
In office
1986–1990
Preceded by Richard Elrod
Succeeded by Michael F. Sheahan
Superintendent of the Chicago Police Department
In office
April 29 – August 27, 1983 (August 27, 1983) (interim)
Mayor Jane Byrne
Harold Washington
Preceded by Richard J. Brzeczek
Succeeded by Fred Rice, Jr.
In office
April 10, 1978 (April 10, 1978) – April 25, 1979 (April 25, 1979)
Mayor Michael A. Bilandic
Jane Byrne
Preceded by Michael Spiotto (interim)
Succeeded by Joseph DiLeonardi (interim)
Personal details
Born 1929
Chicago, Illinois
Political party Republican (since 1985)
Other political
affiliations
Democratic (until 1985)

James E. O'Grady, born in 1929, is a former law enforcement official from Chicago. He held two very important jobs: he was the top police officer for the Chicago Police Department and later the Sheriff of Cook County, Illinois.

Early Life and Police Career

James O'Grady was born in Chicago in 1929. His father was also a police officer, which might have inspired him to join the force.

Joining the Chicago Police Department

In 1952, O'Grady started his career with the Chicago Police Department. He worked his way up through different roles. In 1968, he was hurt during a disturbance when a rock hit him. A few years later, in 1971, he was shot in the hip while chasing a thief when he was off-duty. By the mid-1970s, he became the Chief of Detectives, which meant he was in charge of all police investigations.

Becoming Police Superintendent

On April 10, 1978, Mayor Michael Bilandic chose O'Grady to be the new Superintendent of the Chicago Police Department. This was the highest position in the city's police force. During his time as Superintendent, he made history by promoting the first Black woman to the rank of sergeant. He was also praised for being tough on police officers who were involved in corruption. However, some groups criticized him for not doing enough to stop officers from secretly watching citizens and political groups.

In 1979, during the Chicago mayoral election, candidate Jane Byrne said she would remove O'Grady if she won. She accused him of letting politics influence the police department. After Byrne won the election, O'Grady resigned from his position. He had been Superintendent for just over a year.

Working for Cook County

After leaving the Chicago Police Department, O'Grady worked for the Cook County Sheriff's Office for two years, from 1979 to 1981. He served as the Undersheriff, which is the second-in-command to the Sheriff.

Returning to Chicago Police

In 1981, O'Grady returned to the Chicago Police Department as the First Deputy Superintendent. Mayor Jane Byrne, who had previously criticized him, now said that her accusations about him mixing politics with police work were no longer true.

Interim Police Superintendent Again

On April 29, 1983, Mayor Byrne appointed O'Grady as the interim (temporary) Superintendent of the Chicago Police Department. This was on her last day in office. A few months later, on August 27, 1983, Fred Rice, Jr. became the permanent Superintendent, appointed by the new mayor, Harold Washington. That same year, O'Grady officially left the police force, ending his 32-year career with the Chicago Police Department.

Starting a Private Security Company

After leaving the police force, O'Grady started his own private security company called Special Operations Associates (SOA). He was the CEO for a while. His company was even hired to investigate a difficult unsolved case, and they found important clues.

Becoming Cook County Sheriff

The 1986 Election

In 1986, James O'Grady decided to run for Sheriff of Cook County, Illinois. He ran as a Republican, even though Cook County usually votes for Democrats. He won the election, defeating the current Sheriff, Richard Elrod. This was a big deal because he was the first Republican to win a county-wide election in Cook County in many years.

Before running, O'Grady had been a Democrat, but he switched to the Republican Party in September 1985. He said he had been voting for Republican presidents for a while and felt more aligned with their ideas. Important Republican leaders, including President Ronald Reagan, encouraged him to run.

During his campaign, O'Grady promised to remove political influences from the Sheriff's office. He also pledged to make the jails safer and to fight against corruption. He received strong support from police officers and had a lot of campaign workers and money. The Chicago Tribune newspaper also supported him.

Sheriff's Term and Challenges

When O'Grady first became Sheriff, he was very popular. Some people even thought he might run for mayor of Chicago or governor someday.

However, during his time as Sheriff, there were many challenges. He had promised to get rid of politics and corruption in the Sheriff's office, but it became clear that this was difficult.

Investigations and Problems in the Office

Federal investigators began looking into O'Grady and his Undersheriff, James Dvorak, in 1989. A newspaper series claimed that O'Grady had asked for campaign donations from his employees and given important jobs to his political friends. It also suggested that jobs were being sold and that there was other corruption. After these reports, Dvorak and another high-ranking employee resigned.

Later, investigators looked into a contract worth $1.8 million that O'Grady and Dvorak had given to a company. This company was connected to O'Grady's private security firm. There were also claims that a mob boss had paid money to Dvorak for protection.

Even after O'Grady left office, more problems from his time as Sheriff came to light. For example, an investigator for the Sheriff's office admitted to taking bribes to change test scores for people applying for jobs. It was found that many people got jobs even though they failed the required tests. James Dvorak later pleaded guilty to charges related to bribery and rigging hiring tests. O'Grady himself was not charged.

The 1990 Reelection Campaign

The problems and corruption claims hurt O'Grady's chances for reelection in 1990. During the campaign, an incident occurred where a correctional officer supporting O'Grady's opponent was shot while putting up signs. This caused O'Grady's support to drop.

In 1990, O'Grady lost his reelection bid by a large margin to Michael F. Sheahan. It was one of the biggest losses for a Republican in Cook County in many years. He even lost in areas that usually voted Republican and failed to win any of Chicago's wards.

Electoral History

1987
1987 Cook County Sheriff Republican primary
Party Candidate Votes %
Republican James O'Grady 82,185 100
1986 Cook County Sheriff election
Party Candidate Votes %
Republican James E. O'Grady 706,659 51.21
Democratic Richard J. Elrod (incumbent) 673,233 48.79
Total votes 1,379,892 100
1990
1990 Cook County Sheriff Republican primary
Party Candidate Votes %
Republican James E. O'Grady (incumbent) 136,857 100
Total votes 136,857 100
1990 Cook County Sheriff election
Party Candidate Votes %
Democratic Michael F. Sheahan 719,489 55.41
Republican James E. O'Grady (incumbent) 369,631 28.47
Harold Washington Tommy Brewer 191,101 14.72
Illinois Solidarity William M. Piechuch Sr. 18,318 1.41
Total votes 1,298,539 100
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