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James E. O'Grady
Sheriff of Cook County, Illinois
In office
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
Democratic (until 1985)

James E. O'Grady (born 1929) is a former law enforcement official who served as Superintendent of the Chicago Police Department and Sheriff of Cook County, Illinois.

Early life

O'Grady was born in 1929 in Chicago. His father was a police officer.

Chicago Police Department career

Early career

In 1952, O'Grady became a member of the Chicago Police Department.


In 1968, he was knocked unconscious after a rock was thrown at him during disturbances at the Cabrini–Green Homes. In 1971, while off-duty, he was shot in his left hip whilst chasing a purse-snatcher in The Loop.

By the mid-1970s, O'Grady had become the department's Chief of Detectives.

Superintendent of the Chicago Police Department

After the resignation of James M. Rochford as Superintendent of Police, mayor Michael Bilandic appointed O'Grady as his replacement on April 10, 1978.

In 1978, during his tenure as Superintendent, a police fleeing O'Grady after O'Grady ordered him to stop his car came close to running O'Grady over.

O'Grady promoted the first black woman to the rank of sergeant in Chicago's police force. In his tenure, he won praise for being tough on police corruption. However, the Better Government Association criticized him for failing to sufficiently curb illegal spying by officers on citizens and political organizations.

Another controversy arose when the media reported that police officers were strip searching female motorists stopped for minor traffic offenses. Despite having had an already ten-month long investigation of this practice, O'Grady did not put an end to it until the media reported on it.

Another controversy occurred in the department when Thomas Donovan, then the patronage chief of the mayor's office, called police officers to his home following the arrest of his son for bicycle theft.

During the 1979 Chicago mayoral election, candidate Jane Byrne pledged to remove O'Grady as police chief if elected, accusing him of having "politicized" the department. Byrne defeated Bilandic for the Democratic nomination, and was elected mayor. Days after her inauguration as mayor, O'Grady resigned his position of Superintendent. His tenure as Superintendent was just over a year in length.

Cook County Undersheriff

For a two-year period, from 1979 through 1981, he left the Chicago Police Department to work for the Cook County Sheriff's Office as the undersheriff to Sheriff Richard Elrod.

Return to Chicago Police Department

In 1981, he returned to the Chicago Police Department this time as First Deputy Superintendent. Mayor Byrne rescinded her past accusations that he had politicized the department while Superintendent.

Interim Superintendent of the Chicago Police Department

After Richard J. Brzeczek resigned as Superintendent of the Chicago Police Department on April 29, 1983, mayor Byrne (on her last day in office) appointed O'Grady as interim superintendent. On August 27, 1983, Fred Rice, Jr., appointed by mayor Harold Washington, took over as permanent superintendent.

That year, O'Grady resigned from the police force, ultimately ending his 32 year Chicago Police Department career.

Interim private sector career

O'Grady founded the private security firm Special Operations Associates (SOA), which he co-owned with James Dvorak, Daniel M. Davis, and Mike Caccitolo. He served as its CEO for a while. Amid O'Grady's bid to be Cook County Sheriff, the firm was contracted to investigate the unsolved murder of Diane Masters, and uncovered evidence which pointed to her husband being responsible.

Cook County Sheriff

1986 election

O'Grady was elected Sheriff as a Republican in the Democratic Party-dominated Cook County, Illinois, unseating incumbent Democrat Richard Elrod. He was the first Republican elected to countywide office there since Bernard Carey, who had been elected to his final term as Cook County State's Attorney in 1976. Upon his victory, he spoke of creating, "a new generation of politics" in Cook County. His victory came from winning the county's suburbs by a 2-1 margin. He had also performed well in some of the ethnically white wards of Chicago, being able to carry 14 of the city's 50 wards.

O'Grady, up until then a Democrat, had switched his party registration to Republican in September 1985, in order to run under the Republican Party's ballot line. In switching parties, O'Grady had revealed that in the previous two presidential elections, he had voted for the Republican ticket, and had grown disaffected from the national Democratic party in the recent years. He had been courted by President Ronald Reagan and Vice President George H. W. Bush to run for office. When rumors had arisen in 1985 that O'Grady would potentially challenge Elrod, either in the general election as a Republican or in the primary as a Democrat, Cook County Republican Party chairman Donald Totten actively courted O'Grady to run as a Republican. Other Republicans that courted O'Grady to switch parties were former governor Richard B. Ogilvie, Chicago Republican Party chairman Lou Kasper, and former U.S Attorney Dan K. Webb.

O'Grady's campaign was run by James Dvorak, who he would later hire as Undersheriff once he took office. He was a first-time candidate for political office.

During his campaign he pledged to get rid of political influences in the sheriff's office (such as all political fundraising activities by the office), strengthen jail security, and develop a disaster plan. He also pledged to combat corruption in the office.

O'Grady won the endorsement of the editorial board of the Chicago Tribune.

During his campaign, O'Grady had strong network of campaign workers, and strong fundraising totals. He received strong support from police officers.


O'Grady was, early in his tenure, a popular politician, speculated for a potential future run for Chicago mayor, County Board president, or governor.

In 1988, his undersheriff James Dvorak made a successful bid to be Chairman of the Cook County Republican Party Dvorak had been backed by Governor James R. Thompson against incumbent Donald Totten.

..... This occurred during a restructuring of the office's previously scandal-plagued vice unit.

O'Grady ultimately had failed to live up to his campaign promises of disposing of politics and corruption in the Cook County Sheriff's Office, and had become unpopular among his constituents.

1990 reelection campaign

Corruption allegations took a toll on O'Grady's prospects for reelection.

Amid the 1990 reelection campaign, a Cook County correctional officer was shot and critically wounded while hanging signs for O'Grady's Democratic opponent Michael Sheahan outside of the South Side bar. Three men, including a correctional officer who supported O'Grady, were arrested for this. This led to a decline of O'Grady's support in the polls. Additionally, an incident soon after occurred where Sheahan had a campaign office shot at.

In 1990, he was defeated for reelection by a broad margin by Sheahan. His defeat was one of the biggest defeats that a Republican Party nominee had experienced in a countywide Cook County election in years. Sheahan had managed to beat him in 24 of the county's 30 suburban townships. The ethnically white wards of Chicago, where O'Grady had performed well in 1986, went to Sheahan in 1990, with O'Grady failing to carry a single ward of the city. O'Grady had even failed to carry many of the county's Republican strongholds. Within the city of Chicago, O'Grady even trailed Harold Washington Party nominee Tommy Brewer, who was considered a political unknown.

Electoral history

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 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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