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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.
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.
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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."
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."

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