By Drew Olson and Andy Tarnoff   Published Sep 12, 2006 at 5:36 AM Photography: Andy Tarnoff

It's approaching 10 p.m. on a drizzly weeknight in late August. While thousands of Milwaukeeans are struggling to stay awake long enough to watch the news, I'm riding shotgun in a pickup truck with Dan, a man I've known for only a few hours. We're cruising in and around an area known as Walnut Hill -- one of the more dangerous neighborhoods in the city -- and we are looking for prostitutes.

On the sidewalk adjoining a dark, drab street, we see a tall, athletic young African-American woman who appears to be in her late teens or early 20s. Dan tells me to roll down my window and pulls over to the curb.

"What are you up to tonight?" Dan asks the woman. "Are you looking to party?"

Depending on your perspective, the preceding setup may sound like a work of fiction, a comically embellished account of a bachelor party gone awry or perhaps a rock-bottom "share" from an Alcoholics Anonymous meeting.

The vignette actually took place during one of's two recent "ridealongs" with officers from the Milwaukee Police Department on a vice squad sting. Drew Olson and Andy Tarnoff split up to capture every angle of the action, tonight with new friend and driver, Detective Dan, who is a veteran vice squad detective. He's serving as one of our guides during a memorable tour of a side of the city that many people either don't notice -- or simply don't know exists.

In late June, Olson observed a group of officers from District Six during an afternoon undercover sting operation in a prostitution "hot spot" that runs from 21st St. to 35th St. around National Ave. and Greenfield Ave. Roughly two months later, Olson and Tarnoff returned to the same area with members of the vice squad to watch an afternoon sting looking for "johns" before heading to the near North Side to observe a sweep of prostitutes.

"We could be out here just about every day," says Lt. Bill Potterton, who oversaw the District Six operation. (In order to protect identities of undercover officers, won't use the last names or in some cases the real first names of some officers mentioned in this story. Supervisors like Potterton and Lt. Tom Welch didn't mind being identified.)

"Just about any time you drive through this area, you'll see prostitutes on the street and guys out looking for prostitutes."

Although prostitution is often linked to drug use and other more violent crimes, it seems to rank lower on the public awareness meter / priority scale. That is certainly understandable. Following a three-month period in which Milwaukee police arrested more than 14,000 people, confiscated 752 guns and seized 37 pounds of cocaine this summer, Chief Nan Hegerty recently spoke of a "societal crisis" in the central city.

In the past few weeks, Milwaukeeans were shocked by news of the shooting deaths of Candace Moss, a 13-year-old middle school student who was hit in the heart by a stray bullet while sitting on her neighbor's porch, and Brandon Sprewer, a 22-year-old Special Olympics athlete who was gunned down in a robbery attempt. The city was then repulsed by the multiple sexual assault of an 11-year-old girl, who was coerced by two older teens into having sexual contact on Labor Day with up to 19 men, one of whom was 40 years old. A police spokesperson said that the department has brought 453 solicitation charges this year.

Given that context, it's not surprising that prostitution arrests don't create major headlines. But, that doesn't stop the police from cracking down.

A quality of life crime

"People say it's a victimless crime, and it's not a big deal," says Officer Manny, a beat cop who took part in the District Six sting. "But, it's a big deal to the people who live in the neighborhood. You don't want to see guys driving around like that at all hours. You don't want to see condoms on the street. It's a quality of life thing.

"One Sunday morning, I was driving around, and the streets were pretty much empty. It's always quiet on Sunday. I saw a young girl at a bus stop and she was crying. I asked her what happened and some guy had just come by and asked her for sex, thinking she was a prostitute. She was just waiting for a bus to go to church. I told her,'Get in the car,' and I gave her a ride. I didn't want anyone else bothering her."

Officer Manny carries a small notebook that is packed with booking pictures of all the women he has come in contact with over the past several years. For people to whom the word "prostitute" conjures images of Julia Roberts in "Pretty Woman," Manny's book could be a shock. The women pictured look hardened and most are in throes of drug addiction.

"They're not out on the street because they're nymphomaniacs and they love sex," Detective Dan says during the North Side sting. "They've basically sold everything they have and now they're reduced to selling their bodies.

"Prostitution is just fueled by crack addition. I'd say 95 percent of prostitutes on the street level are addicted to crack cocaine. Years ago, it was heroin. Now, it's almost exclusively crack. Once in awhile, you run into a heroin addict. But, it's mostly crack."

Welch said that street prostitutes in Milwaukee charge anywhere from $20 to $40 for a oral sex and $40 to $100 for intercourse. "You might get a girl (to perform) 'half and half' for 20 bucks," he said. "It just depends how bad she needs the money and how much you want to barter with her."

Detective Dan and I are standing at the temporary command post, where police had set up a van behind a vacant building to house and begin processing the prostitutes picked up in the sweep. "Come on, let's go for a ride," he says. "We'll see what's going on with the guys out there."

Our intent is to check on the police officers posing as johns for this operation. But, we get into it a little deeper when we see Shauna (not her real name), standing across from a car in which another woman, whom Shauna said is her sister, is reclining on the passenger side.

"What are you guys doing?" Shauna asks. "It's his bachelor party," Dan says, motioning toward me. "We're looking to have a little party at our place over on the East Side. Do you want to party with us?"

Uncertain what is going to happen and not wanting to screw up a potential arrest, I slide my left hand under my leg so Shauna can't see my wedding ring. What bachelor wears a ring to his bachelor party?

Detective Dan engages Shauna in a discussion / negotiation. In a few minutes, she agrees to have sex with both of us for $50. "Hop in," he says to Shauna. Then he looks at me and says, "Get out and let her sit between us."

During afternoon operations on the South Side, police put female decoys out on the street and wait for johns to approach them. It seldom takes long. The female officers are not equipped with microphones or radio transmitters and almost always unarmed.

"Sometimes in the winter, you can conceal (a gun)," one of the decoys says. "Not in the summertime. There is nowhere to put it."

The decoys are watched from a distance by a "shadow" or "cover" officer, who remains in radio contact with a "takedown" car a short distance away.

Hurry up and wait

At 3 p.m., the takedown car is parked in an alley off National Ave. and the two young police officers are displaying a calm, almost Zen-like approach to their assignment with the vice squad. During these occasional sweeps, Lt. Thomas Welch of the vice squad asks supervisors from different districts to provide officers to help with the operation.

"It's another day, for the most part," says the officer behind the wheel, undercover in a 49ers jersey, white visor and bulletproof vest. Even though it's one of the most prestigious responsibilities in the force, both cops seem somewhat unfazed.

"You don't get picked for doing anything special," says the second. "But it's a nice change of pace."

Almost an hour passes before the first arrest. The shadow car announces each potential pick up over the radio. "Tan Saturn," it squawks. Then about 10 seconds later: "No go."

A few minutes later, we hear, "Black Nissan, four-door." Then again, "No go."

The officers put the unmarked car back in park and continue talking about family, the dangers on the job, but mostly about all the paperwork that comes with police work. It's not, they say, all about busting bad guys. "There's a continuum of things you go through," says the officer who is riding shotgun.

After about 40 minutes, the decoy has found a john and given a signal to the shadow officer. "Red Civic," the radio announces. "Go!"

And just like that it's a scene straight out of any TV police show. The officers slap the portable siren on the dash, crank it up and floor it around the alley. They spring out of their car, surprising the young suspect in the Civic hatchback. He's more clean-cut than you might expect, wearing work clothes, looking like he just ended his shift at a nearby mechanic shop.

The suspect is completely stunned as the officers cuff him, put him in the back of the red Crown Vic and take him to the staging area a few blocks away. They quickly search his car and begin to interview the suspect, who will eventually sit for the next several hours in the back of a van filling with sullen-looking men.

"He's looking at a $500 fine," says one of the officers before he heads out for another pick up.

The johns caught in sting operations come from every social, racial and economic strata of the city. Some are laborers driving company trucks, which are impounded until a representative from the business comes to get them. One man recently propositioned a decoy while riding a bicycle, which was impounded, and another came up on a motorcycle, which was tucked away near the command post.

Some of the johns are white-collar workers. Recently, a suburban police officer was arrested for offering a decoy $15 for oral sex.

Although many johns are considered not dangerous, some are under the influence of alcohol or drugs, some are carrying weapons or drugs and others get nervous because they are on parole.

"Most of them just kind of hang their heads and say, 'Don't call my wife,'" Welch says. "One or two sweeps ago, we got a guy who was a bigwig at a bank. The first thing he did was call his wife and say, 'Hey, I just got arrested, well, you know, in that part of town where we go once in awhile ...' It turned out they were swingers and they would pick up prostitutes together."

Off the streets

Prostitution in Milwaukee is not limited to street activity. At the other end of the spectrum are escorts who work in hotels and nightclubs and often get customers through ads in newspapers or online.

"Somehow, they think they are better than the street girls," Detective Dan says. "But, they're doing the same thing. These women can charge anywhere from $100 to $500 an hour for their services. They'll do it in a hotel room or wherever."

Dan recently arrested a 43-year-old escort; a single mother with two older children, a good job in the medical field and a nice home in Glendale.

"She had rented an apartment downtown," he said, referring to the new units near police headquarters. "She figured it was more cost-effective to rent an apartment for $1,000 a month than spend $60 to $70 for a hotel room every time. So, she furnished this apartment and used it for the sole purpose of engaging with her upscale Milwaukee clientele. She was good looking, in good shape for her age and she was doing it for the money. She had regular clients and she was charging $250 per trick.

"She got charged with operating a place of prostitution. It doesn't matter whether you're using it for yourself or with 20 girls - if that's the primary purpose, it's a whorehouse."

A spontaneous act

During a stint in the "cover car" Detective Dan said that many of the johns are acting spontaneously. As he speaks, several cars slow down and talk to the decoy, but none proposition her. First, it's a brown sedan that stops to chat, but leaves, presumably spooked. Then it's a silver mini van ... nothing. Next a black Toyota Highlander makes two passes, so does a Corolla. Later, the decoy will tell me that she had each of the license plates memorized by the time the cars passed by. She paces back and forth, looking casual as can be -- but all of her senses are piqued and alert.

At 4:11 p.m., the silver Corolla makes another pass. The driver stops and tries to get the decoy into his car. "I just want to talk, why don't you just get in?" he says to her. Something must feel wrong to the driver, because he changes his mind and leaves.

A few minutes later, a red Camry pulls up to the decoy officer. But he sees the cover car watching from the parking lot, and leaves in a hurry. "He's been scoping (the decoy)," says the lieutenant.

Finally, the decoy motions us over and suggests we try another corner. We move a few blocks south and east and park a bit father away.

At 4:42 p.m., a pedestrian approaches the decoy, who is now standing on a corner in front of a school. He walks away, but two minutes later, another man walks up. We might be in business.

After a short conversation, he leaves, too, but at 4:56 p.m. he comes back, holding a paper bag in his hand, concealing a 40-ounce bottle of malt liquor. A few moments later, the decoy gives her pre-determined sign that she's been propositioned and it's time to move in. The lieutenant gives the take-down call over the radio, and we watch as an unmarked police car pulls up -- mere seconds later.

The suspect, visibly intoxicated, doesn't even know what's happening until the two officers are perhaps six feet away from him. They slap cuffs on him, while our decoy returns to the truck.

"His speech was slurred, but he didn't smell like booze," she says.

According to the officer, the conversation was relatively straightforward. First, the suspect asked if the decoy would have sex with her for free, then asked specifically for oral sex. He pointed down the street and suggested they go back to his house. He asked her how much; she replied "$20." According to the decoy, he said in broken English, "OK, we go to my house."

Occupational hazards

One of the female decoys was involved in a scuffle during a recent sweep, but it wasn't related to prostitution.

"She was on the southwest corner of the street and there was a corn vendor on the southeast corner," says Welch. "Three suspects ran up to him and started pounding the s--- out of him. They were going for his pockets. She decided to come out of her undercover role. She had her ID on her, but that's all she had. One guy turned on her and just labeled her five times to the head. We couldn't get across the street quick enough. She was down, but she grabbed the guy again. The takedown car and cover car got there and we got two of the three guys, the other one - who spit on her - got away. She was OK. There were no major injuries. In fact, she came back the next day. She's a tough girl; a good cop."

John the john

At 6:55 p.m. on the South Side, a call comes over the radio to take down a blue van that just propositioned one of the other three police decoys. The stunned suspect is a scruffy, older, toothless and drunk man named, ironically, John.

The officer riding shotgun takes the van back to the staging area, while the cop with the white visor, takes the suspect back in the police car. He drives quickly, very quickly, as John the john grunts in the backseat.

"What were you doing out there, John?" he asks, politely.

"I was just going to Popeye's," John slurs. "I've been home all day, and I went out because I was bored. I saw (the decoy) and thought maybe she wanted to a ride."

The officer asks if John is married and if he has any prior arrests. John says he's 65 and single, and did time in Oklahoma for armed robbery many years ago.

Flipping the sting

With the afternoon operation on the South Side complete, the officers return to headquarters to pick up unmarked cars, all of which were seized in other crimes, and take a quick break for dinner. The operation at night is flipped: the female decoys are now in charge of booking and interviewing the women being picked up for prostitution.

The men are posing as johns, which is a dangerous, and very solo, operation.

The officers go "radio silent," relying on their experience and instincts to pick up the prostitutes. They're still armed, but their pistols are concealed, usually behind their backs. Many of the suspects are armed, too, usually with box cutters in their purse. Nearly all of them, the officers say, are drug addicts, but few of them have drugs on them when they're arrested -- probably because they've already smoked their crack and are out raising money to buy more.

The unmarked decoy cars are non-descript. The men from District Six explain that savvy prostitutes connote a lack of trash - fast food bags, newspapers, soda cans - as a sign that it's an undercover police car.

"We had one girl make our guy look at the pen in the car," says an officer, holding up a black PaperMate ballpoint. "She said, 'You're the Po-po. That's a Po-po pen.'"

Some undercover johns will stock their cars with props. A hard hat. A lunch box. Some tools.

Suspicious behavior

The North Side operation has a different tone than the South Side. While the johns seem embarrassed and hapless, the prostitutes, for the most part, seem desperate and pathetic.

You wonder how police can avoid depression seeing things like that on a nightly basis. Welch says that camaraderie between officers helps, but admits that it can be difficult for cops to avoid becoming jaded by what they see.

"When I first started on the job, my mom wasn't worried about me taking a bullet," he says. "She was worried about me becoming hardened. For me, it's my family and my faith that gets me through." Separately, the cop who was riding shotgun earlier says the exact same thing.

Although officers call it a slow night -- maybe the drizzle is keeping people off the streets -- the arrests start pouring in. A 52-year-old well-dressed woman named Helen is picked up. She seems sad and frustrated, but resigned to her fate. Another prostitute, who claims she's not a regular drug user and this is her first arrest, is already sitting in the van, joking with officers and other suspects. She's prettier and more intelligent than the rest, and nearly everyone comments later that she could be doing better with her life.

Riding with Lt. Welch, we drive back and forth down North Ave., looking for suspicious behavior. There seems to be a ton of it.

Now close to 10 p.m., many people are milling about the streets. But the police are only going after the hookers tonight. The women who are alone, making eye contact with our SUV, are the ones who will eventually wind up arrested in our staging area. Almost all of them have drug paraphernalia in their purses.

Sometimes, the women resist more than the men. "It's funny," says one officer. "You can see two of us take down a drunk guy who is 6-foot-4 and weighs 250 pounds without a major problem, but it can take five of us to subdue a 5-foot, 90-pound prostitute who is on crack."

Shauna's take down

It's a long drive from the point where we picked up Shauna to the command post, and Detective Dan is making small talk to keep her from getting suspicious. In what I thought was an inspired ad-lib, I had said that I needed to hit an ATM in order to get her money.

"You're sexy," he says. "Do you work out?" When he includes me, I try to play along. "Do we have any beers at home?" he asks. "We better," I say. "If those assholes drank 'em all, I'm going to be pissed."

Dan asks Shauna what she likes to do. She asks if we smoke crack. "We've got some weed," he says. "We don't do crack. Do you do that?" Shauna says, "No. I don't do any of that."

Shauna seems relaxed, which makes me think she's happy to be off her feet or thinking about the money she is about to make. After a few minutes, she stares out the window and asks, "Where are we going, anyway?" Dan says, "We're going to our place on the East Side, just across the river. I don't to do anything here because there are cops around." I reiterate my need to hit an ATM.

As we wind through side streets and near the alley where the command post is located, Dan asks me, "Where is that ATM?," to which I reply: "Man, I thought you knew!" Detective Dan asks Shauna, "Where are we, anyway?" Shauna says, "You don't know where you're going?"

With that, Dan pulls into the alley and interlocks his right arm with Shauna's left arm. "We're the Milwaukee Police, honey," he says, zooming up to the command post. I jump out of the truck and let the other officers take Shauna into custody. She seems too shocked to resist.

As she is taken toward the holding van, Detective Dan smiles at me and says, "You can't get any closer than that." A few minutes later, another cop jokes about my being "deputized" and asks Detective Dan how I handled the situation. "He s--- his pants," Dan says, laughing. "No, he was fine. Of course, now he might have to testify in the case."

During questioning, Shauna shows a bit of a cagey side. She claims she doesn't have an address because she is homeless. (A lot of people lie to police for various reasons, including prior offenses, parole status, etc.) Detective Dan tries to speed the process. "You better start cooperating," he says. "If you cooperate, I'm only going to charge you with one count. I could charge you with two, because you agreed to do both of us. So, tell us what we need to know and this won't be a big deal."

Legalize it?

As the night progresses, we watch a half-dozen undercover johns pull into the alley with prostitutes of all shapes and sizes on the passenger side.

A few of the women already in custody begin to shout, usually proclaiming their innocence, but the alley remains mostly quiet.

"We're lucky," one officer says. "They're behaving themselves pretty good. Sometimes, you get one that's riled up and it can get pretty ugly."

We ask Detective Dan whether he agrees with some who say that prostitution should be legalized or allowed to go on in a "red-light district?"

"I understand why people say that, but I'm not for legalizing anything that isn't a betterment to society," he says. "That's a question you hear with all the vices. Why don't we legalize drugs, gambling and prostitution?

"Well, as you legalize it, you've got to regulate it. Think about all that would go into the regulation and compliance and overseeing these women and the millions of dollars you're going to spend on that.

"You're not going to take away the illegal activity. When gambling was legalized in this state, they created an entire Wisconsin gaming commission to oversee the dog tracks, the casinos and the lottery. We spend millions of dollars on that, so we don't have any illegal gambling in Wisconsin, right? Don't fool yourself. You can go to your local tavern and play a slot machine or put down a bet on a football game.

"If you go to Nevada, prostitution is legal everywhere but it's not in the city limits of Las Vegas. Well, there is an inch of hookers' full-page ads in the Vegas phone book. Every casino has hookers in it and they're walking down the streets.

"The way I look at it, you're not going to eliminate illegal stuff, so what are you going to gain?

"People who talk about putting (a red-light district) down in the Third Ward or in the valley; well, who wants to live over there? A lot of people want to legalize it, but they don't want to live next to it.

"I don't know the answer. I just know that as long as it's illegal, we're going to be out there trying to stop it."