A lacy pink bra and a blonde shag wig are two of the more curious artifacts tucked away at the Minnesota Historical Society. Both belonged to pioneering St. Paul police Lt. Carolen Bailey, who took down criminals and gender barriers during a 36-year law enforcement career that began in 1961 and included stints as a homicide investigator and vice squad commander.

With sergeant stripes sewn on each cup, the size 36DD bra was a gag gift presented to Bailey in 1971 at a dinner to celebrate her promotion as St. Paul’s lone female sergeant. Today women in the department make up more than 40 of its supervisors or commanders.

“In those days, people weren’t quite so sensitive but I thought it was a riot,” Bailey said of the bra. “Today? Oh, my gosh, someone would get suspended.”

Bailey, who lives in North Oaks, turns 84 next month. Along with being Minnesota’s first female police lieutenant and patrol commander, she was the state’s first female cop to dress like a street prostitute and arrest johns. That’s why the Historical Society included the wig in a vanload of artifacts it hauled away for preservation.

In 1974, a Minnesota judge ruled it was discriminatory for male cops to pose as customers to bust prostitutes if female officers weren’t going undercover to book johns. So Bailey volunteered to stand at Selby and Western avenues in a tight yellow sweater, short red skirt and that blonde wig.

Former St. Paul Police Chief William McCutcheon, who died in June at age 93, was a deputy chief at the time and noted that most prostitutes on the corner were far younger than Bailey, then 37.

“He said, ‘Well, we’ll try it, but I think you’re too old.’ And I never let him forget it, because the first hour and five minutes, I had 11 arrests and that total day, I had 60,” Bailey recalled in a fascinating oral history recorded in 2007 by police historian Kate Cavett (tinyurl.com/BaileyOralHistory).

“She did a great job with every assignment she had,” McCutcheon said in 1991. “She broke a lot of ice.”

Born Carolen Fay Gesin in Osceola, Iowa, in 1936, she spent her childhood in Brazil, where her father managed South American operations for International Harvester Co. She returned to graduate from Johnson High School in St. Paul, where she met Roger Bailey, her husband of 64 years. She earned a four-year degree in social work and psychology at the University of Minnesota in two years. “Doubled down on credits,” she said.

After a four-year stint as a case worker in child protection for Ramsey County, she was forced to quit with the pregnancy of her second son. Restless to work, she figured the police might have off-hour shifts enabling her to stay home with her two boys during the day.

Of 25 women tested by St. Paul police in 1961, Bailey was the only one hired and became only the third woman on the force. After two years in the juvenile division, and pregnant with her third son, Bailey again had to quit. But she was rehired after nine months off, at the same salary, and stepped into new turf for women cops: investigating sex crimes, robberies and homicides.

“I really enjoy the good homicide where you can put the pieces of the puzzle together and they fit,” she said in 1980. Along the way, she also taught law enforcement and served as president of the International Association of Women Police.

Her gender helped in incest cases, she said, because girls assaulted by their fathers were more likely to open up to a woman. Her direct approach also helped bridge the gap with male officers.

“I didn’t pretend to know it all and I made it very clear that I had a lot to learn and that I wanted to learn from them,” she said in her oral history. But she assured them that she learned fast.

Bailey helped convict Robert Pietraszewski in 1969 of raping and beating a 16-year-old babysitter to death with a car jack. She helped secure pivotal voiceprint recordings of the caller who lured police officer James Sackett to a fatal 1970 ambush.

In 1983, she helped put away the powerful owner of a nursing home where a mentally disabled woman died. When FBI agents had trouble serving a subpoena on a man making terrorist threats, Bailey had one of her officers dress up as a pizza delivery guy and slip the subpoena to him in the pizza box.

“She busted swindling fortunetellers, arrested a beauty operator who was sexually molesting his customers, and staked out the bedroom window of an exhibitionist who danced nude in front of female passersby,” wrote Star Tribune reporter Conrad deFiebre when Bailey retired in 1991.

That retirement didn’t last long; she joined the state Department of Public Safety and served as an assistant commissioner for five years.

Today she watches the “Me Too” movement collide with calls to defund police after George Floyd’s death.

“That was horrible and, in my 30 years, I never saw a chokehold,” Bailey said. “But to make generalities about all police isn’t fair. And cutting off funds when crime is so high? I’m just worried about what people will think when there’s an issue and no one’s there to come out.”


Curt Brown’s tales about Minnesota’s history appear each Sunday. Readers can send him ideas and suggestions at mnhistory@startribune.com. His latest book looks at 1918 Minnesota, when flu, war and fires converged: http://strib.mn/MN1918.