I would sometimes rather do an investigation in a really bad neighborhood than in a rich area. When you're in the inner city, nobody cares why you're there. Some strange car on the street? Not my business! When you go to wealthy areas, though, people are on the lookout for anything that doesn't belong.
I ran a case earlier this year in downtown Chicago. The guy I was to investigate was on disability for depression. He was a venture capitalist and lived right on the lake by Navy Peir. The mirrored glass and marble high-rise building he lived in housed condominiums that must have cost at least a million each. Nice.
I started humming:
"I'm movin' on up.
To the east side.
To that deluxe apartment in the sky-hi-hi..."
At the time, I was driving a beat up '92 Ford Aerostar. Generally, it was perfect for surveillance. A vehicle more suited to a soccer mom than a P.I. But in this neighborhood, I stood out like a sore thumb. Every car I passed was a high-end luxury vehicle.
5:53 a.m. I drive by the building and note that the lobby is protected by 24-hour security personnel and two key-entry side doors. I watch a bay door open on the side of the building. A Mercedes pulls out and takes a left. Inside the bay door I see a security guard/valet manning the parking structure. And no off street parking for blocks. Great. This is going to be tough.
I end up setting up a surveillance position in the loading zone across the street with a clear view of the front door and lobby. Time to make a plan.
I don't even know what my Subject looks like. The only information I got from the insurance company is that he's a 37-year-old white male. Gee. That narrows it down to 2/3 of the men in the building. If I don't get a visual on him there is no point in my sticking around all day.
I decide to be Susan Johnson, of Omni Flower Delvery Service. I call Subject and tell him there is a delivery for him and will he be around to sign for it? Subject seems delighted and asks me who it is from. "I don't know," I say. "It's anonymous." He seems to accept that, but then asks, "Is it from Florida?" (This is where being a good liar comes in.) "It could be. We get our orders from several different flower shops in Northern Illinois. Those flower shops fill orders for a bunch of online websites that service the entire U.S. By the time it gets to me it is so far removed from the source that I really couldn't tell you were it originated." But he isn't so easily placated. "Don't they track that? They must keep a record of where the orders came from." (When all else fails, play dumb, ignorant, and helpless.) "I don't know. I'm just the delivery girl."
So, we set up a time that afternoon for me to bring him the flowers. I leave and go to the local Home Depot to hang out for a couple of hours. I love that store. I could spend a fortune there. It was the funniest thing walking around. People in designer clothes and sunglasses. Full length fur coats and high-heeled leather boots. Fabulous accessories. It was like some trippy celebrity gathering, only instead of a trendy club or restaurant, it was the Home Depot. I guess even the obscenely rich have home improvement projects.
12:46 p.m. Time to get ready. I go back to my van and hop in the back. I keep my disguises there. I pull on some tan Dickies, a bright blue polo shirt, and a black wind breaker. I gather my hair back into a ponytail and put on a blue ball cap. There we go. Delivery girl at your service.
Oh! Almost forgot. Gotta get the flowers.
I check online and find a flower shop not too far from here. I pick out some daisies and a yellow vase. I fill out the card from "Anonymous" and make sure the envelope and note card are not marked with the flower shop's name and address. Good. I don't want him to have any way of tracing the origin of the package.
I go back into my van to prepare a proof of receipt for him to sign. First I dash off a few bogus names and signitures of people I'd already deliver to that morning. Gotta make it look authentic.
1:25 p.m. I park in the loading zone outside the building. I walk inside to the desk where the doorman is sitting. He looks annoyed with me and I haven't even spoken yet. This is a new record for me because usually it takes at least a minute or two of conversation before I start to annoy people. "I've got a delivery for Subject in #1203." He looks at me suspiciously and asks me to sign a registry. While I'm doing that, he's calling up to Subject's residence. "You can go right up," he says.
I take the elevator up to the 12th floor and walk down the hall toward the residence. I can feel my hands sweating a little bit. When I knock on the door, a young girl about 10-years-old answers. I ask her if Subject is there and she says he's not but will be back soon. Ugh! I thank her and say I'll try again later.
Great. Now what?
I take the elevator back down and am just writing a message for Subject at the front desk when this gorgeous man, curly brown hair, 6'2", 190 lbs, and built like an Andonis, runs out of a stairwell. He is breathing hard. He smiles and asks me if I'm Susan. I am a little bit dazzled. Susan? Who is this "Susan" you speak of? And what sparkly blue eyes you have... But then I remember that I AM Susan. Susan, the flower delivery girl. Darn it!
We chat for a few minutes and he takes his flowers. He seems very pleased with them and wonders out loud who they are from. "Looks like you have a secret admirer," I tell him. Another great big smile and he's gone.
Didn't look very depressed to me. And what would he have to be depressed about, anyway? Rich, gorgeous, living off the backs of the hard-working public...
I walk back to my van and consider. He works out. That's obvious. Do depressed people work out? If they are well enough to workout aren't they well enough to hold down a job? Wonder where his gym is? And even if I DO get footage of him, how am I supposed to visually document depression?
An hour later he calls me on my cell. Normally, I will block my number so that Subjects won't be able to trace calls to me. In his case, he asked for my number because we were having trouble coordinating a delivery time. He asks me about who might have sent the flowers, again. I tell him I don't know but will check with my boss. He asks me out on a date. I politely decline. I can just imagine if I did go out with him. By our third date, I would have to break it to him that my name is not Susan. I would then have to break it to him that I'm not a flower delivery girl. Then I would have to explain that I am a private investigator who was sent to spy on him. "But hey, baby...don't let the fact that our relationship is based on a lie wherein I was attempting to entrap you for insurance fraud affect any possible future we might have together!"
Some P.I.'s would jump on that and use going on a date with a Subject as a means to gather information. I won't cross that line.
More later on this case.