The Billionaire Bum

By: Samantha Blair

I left the courthouse and went across the street to the post office to have the money order made. The total in my wallet was reduced to $21.74, but I was one step closer to a job.

They still hadn’t called my number when I returned, but thankfully this line was not as long as the other. The birth certificate proved to be easier than I thought. I was afraid that there could be a waiting period, but they were able to print me a copy while I waited.

It was now 4:30 pm. I knew that I couldn’t make it back to the social security office by 5:00, and even if I could, I was short sixteen dollars. It seemed more logical to head over to the shelter.

Perhaps I could borrow the money from one of the shelter workers if I explained the situation? I could pay it back as soon as I got my tips the following night.


I had to give him some credit. Jackson hadn’t given up yet. Granted, he hadn’t come across any real trouble yet either. I hoped his luck would hold out.

I’d started following him last night as soon as Jason had called. Jason thought it was likely that he would head out to the airport. Apparently, it was one of the places that Jackson felt most comfortable, and Jason was right. We’d found him there, asleep, about an hour before the security guard woke him.

Once you lost a subject it was much harder to find them again, which meant that we were working around the clock. I had Sean, another bodyguard, following him during the day, and I was taking the night shift.

I’d placed a few phone calls today and had gotten a full report on the homeless scene.

Fortunately, my work didn’t usually require spending the night in shelters and eating in soup kitchens, but I knew from past experiences the right questions to ask. I’d gone through enough rough patches in my life to understand what it meant to be uprooted and alone in a city. It was not easy, but it was manageable if you could establish a routine that involved eating at least once a day, sleeping somewhere safe, and staying out of the elements.

According to Sean’s report, Jackson had actually done really well today. He’d found a bar-tending job and gotten a copy of his birth certificate. He’d need a social security card to be able to work, unless he found someone who was willing to pay him under the table. If he was able to work, he might just make it through the week. He was more resourceful than I’d given him credit for. I thought for sure he’d spend the first night in a cheap hotel and go home as soon as he realized that there were cockroaches in the tub.

What concerned me now, however, was the subway stop. I’d been sitting four rows behind Jackson on the subway talking with Sean, but after he’d finished his report he headed off home leaving me to follow Jackson alone. Sean hadn’t been sure where he was headed. He knew that Jackson had gone into a couple of churches earlier, but he hadn’t heard the conversations that took place indoors, so we weren’t sure what information he had obtained. We thought that it was safe to assume that he was looking for a place to spend the night, most likely a homeless shelter.

Homeless shelters were usually unsafe at best and could sometimes be downright dangerous. There were four in the city, and unfortunately, the subway stop where he was now exiting was only close to one of them—the worst possible choice. Most shelters would turn you away if you appeared to be high, severely intoxicated, or likely to stir up trouble for another reason. This one did not. For someone like Jackson, coming here was like begging for trouble.

Would he know that? I doubted it. I didn’t think that he would have had any reason to visit this place in the past. Shelters weren’t usually on the radar of the extremely wealthy. The Hayes were good people, they gave a lot of money to a lot of good organizations, but they were the type to hand over large checks at fund-raising banquets, not the type who volunteered to scrub toilets in homeless shelters.

My fears were realized when Jackson pulled on the locked shelter doors. This was going to be a long night.

I stayed out front and watched him walk up the alley looking for a back door. If he found one, it would be locked as well. Everyone planning to stay the night in the shelter would line up in front of the building starting around 7:30 in the evening. They would let the homeless guys in around 8:30. Lights out at 10:00. A privileged few would manage to get into the showers before lights out. The other would try in the morning before they were evicted. Only about a third of the guys would actually get a shower. During the colder months the shelters would be packed full.

They would still be crowded this time of year, but some people would prefer sleeping outside to being here, even if it did get down to about forty-five degrees at night.

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