Police Work: Undercover as a prostitute with Carolen Bailey

Carolen Bailey walking University Avenue as a police decoy prostitute in 1974

I graduated from the University of Minnesota, worked for Ramsey County Welfare Department, and then in 1961 I was hired as a Saint Paul police woman at what was basically a detective-level salary ($200-something a week). Police women were required to have a bachelor’s degree. I began in the juvenile department, then Chief McAuliffe transferred me to the homicide unit.

Judge Bertrand Poritsky ordered that if police officers wanted to work undercover to arrest female prostitutes, they would also have to use women officers undercover to arrest male customers to avoid being discriminatory. So when that order came from the court, I went into Assistant Chief Bill McCutcheon’s office and told him that I wanted to do this—that it was a great opportunity, and I believed in the equality of it.

Most of our prostitution problem at that time was on Selby and Western. Most of the girls working that area were twelve-, thirteen-, and fourteen-year-olds, very young girls. When I told McCutcheon that I should do this, he said, “Well, we’ll try it, but I think you’re too old.” And I never let him forget it, because that first hour and five minutes, I had eleven arrests, and that first whole day, I had sixty.

Here is a picture signed in 1974 from the very first case I ever worked on. I had just pulled off my blond wig when Sgt. Paul Paulos pointed his camera at me, so I put the wig back on crooked, because I really didn’t think he’d take the photo.

I wore colors that would remind anyone of a street light—bright red stop signs and yellow slow-down colors.

In the early years, when I was in Juvenile Division, most of the undercover work involved illegal after-hours clubs; it often was associated with drugs and, of course, sale of alcohol and prostitution, so a lot of crimes developed from those clubs. I went into a lot of them more than once. I just changed my appearance. In one case, José Flood—I raided him seven times, got in every single time, looking different—he’d say to me every time, “I’ll know you next time.”

There was a club called the Turtle Club that was infamous—there were so many problems about it, and nobody could ever get in. So I went over in Minneapolis and made connections with people who were going to go into the Turtle Club. I took a spit sample of the liquor I had while I was in there, and they came in and raided it.

It ended up in the newspaper. I went over to one of the detectives to talk to him when they raided the place, and a uniform patrol officer said, “Look lady, you’re not leaving here.” And the detective laughed and said, “Don’t you know who this is?” And they explained who I was, and we all laughed, and that was the end of it.

The next morning I was called into the chief’s office ’cause he was very alarmed that I had been mistreated. The newspaper quoted me as saying it was the most harrowing experience in my career to be arrested and hauled away. I told Chief Lester McAuliffe that that didn’t happen, and he was reassured. He was very protective of me, and he used to say to the officers who were my backup, “If one hair on her head is damaged, mail your badges in, don’t come in.”


This is an oral history excerpt with retired Officer Carolen Bailey, as told to Kate Cavett of HAND in HAND Productions, for the Saint Paul Police Oral History Project. Oral history is the spoken word in print. Oral histories are personal memories shared from the perspective of the narrator. By means of recorded interviews, oral history documents contain spoken memories and personal commentaries of historical significance. These interviews are transcribed verbatim and minimally edited for readability. The greatest appreciation is gained when one can read an oral history aloud.

Leave a Reply