St. Paul in the late 1920s and early 1930s was known as a “‘crooks’ haven”—a place for gangsters, bank robbers, and bootleggers from all over the Midwest to run their operations or to hide from the FBI. The concentration of local organized crime activity prompted reformers and crime reporters to call for a “cleanup” of the city in the mid-1930s.

The March 1963 murder of St. Paul wife and mother Carol Thompson shocked the Twin Cities as few local crimes have. Despite community fears of a homicidal maniac, investigators soon focused on T. Eugene "Cotton" Thompson, the victim’s husband, as their prime suspect. Three and a half months after the murder, Thompson was arrested and charged in connection with his wife’s death. In December 1963 he was convicted of first-degree murder and sentenced to life in prison.

In 1977, residents of South Minneapolis mobilized to fight the expansion of adult entertainment businesses along Lake Street. In 1983, after years of unsuccessful protest, these activists sought help from nationally known feminist theorists Catharine MacKinnon and Andrea Dworkin. MacKinnon and Dworkin wrote a controversial amendment to the city's expansive civil rights ordinance that defined pornography as a violation of women's civil rights.

On July 27, 1972, two armed, masked men walked into the Orono home of Virginia Lewis Piper and walked out with the forty-nine-year-old woman handcuffed and blindfolded. The next day, her husband, Harry C. Piper Jr., a prominent Twin Cities investment banker, personally delivered a $1 million ransom to the unidentified kidnappers. Four decades later, no one has served a day of prison time for the crime. Except for about four thousand dollars in scattered twenty-dollar bills, the Pipers’ million-dollar ransom has not been recovered.

Edward Foote Waite was a distinguished Minneapolis judge and community leader. His involvement in public affairs spanned much of the twentieth century.

The 1889 death of inmate Taylor Combs led to a scandal, and then major reforms, at the Rochester State Hospital for the Insane.

The O'Connor layover agreement was instituted by John O'Connor shortly after his promotion from St. Paul detective to chief of police on June 11, 1900. It allowed criminals to stay in the city under three conditions: that they checked in with police upon their arrival; agreed to pay bribes to city officials; and committed no major crimes in the city of St. Paul. This arrangement lasted for almost forty years, ending when rampant corruption forced crusading local citizens and the federal government to step in.

The Minnesota Commission of Public Safety (MCPS) was a watchdog group created in 1917. Its purpose was to mobilize the state's resources during World War I. During a two-year reign its members enacted policies intended to protect the state from foreign threats. They also used broad political power and a sweeping definition of disloyalty to thwart those who disagreed with them.

Ann Bilansky was the only woman executed by the action of Minnesota courts. She died in 1860, but doubts about her guilt remain alive.

In the early morning of June 2, 1895, Houston Osborne, a young African American man, broke into Frieda Kachel's bedroom in her St. Paul home. When Kachel screamed, Osborne ran; he was caught and hanged from a cottonwood tree but let down while he was still alive. He died in prison eighteen months later.