The Billionaire Bum

By: Samantha Blair



Many of Jackson’s soon to be bunk-mates were eating at a church about six blocks from here, but Jackson didn’t know that. He had to be getting hungry by now. Sean said that he hadn’t eaten anything but pancakes all day.

When dinner was finished at the church, the homeless would congregate here in front of the shelter until they were allowed inside. We had about fifteen minutes to go until Jackson would encounter his first taste of what real homeless people were like.



He circled the building. When he didn’t find another open entrance he walked to the end of the block and back as if verifying that he was in the right place. A few minutes later the first man showed up with a plastic shopping bag under one arm. He ignored Jackson and shuffled back and forth in front of the shelter steps.

I pulled up the hood of my sweatshirt and moved closer. I doubted that Jackson would recognize me. We’d only met one time, and it had been several years ago. We were also at Jason’s wedding together, but we didn’t speak to each other as there were about seven hundred people in attendance, including half the politicians in the state. The Hayes family knew how to throw a great party.

I wanted to be close enough to save Jackson’s ass should he get into a fight, but far enough away to keep my cover. Jason had made the rules pretty clear to me. “Don’t let him get killed, but don’t help him either.” I chuckled under my breath. Jason was a riot.

That meant, though, that I couldn’t give Jackson the information that he needed. He was going to have to learn how to communicate with the homeless if he wanted to keep eating. It took a few minutes before Jackson even noticed that people were beginning to congregate in the street. He appeared to be in his own little world. That seemed pretty on par from what I knew of the guy–nice enough, but clearly self-centered.

Finally, he wandered over to a group of three guys who had all come together. I was fairly certain that they had walked up from the soup kitchen as a group. Homeless people had needs that went beyond food and shelter. Humans are pack animals. We all feel the need for social interaction, although some more than others.

“Is this shelter open tonight?” Jackson asked the guys.

They appraised him for a few seconds before one of them spoke up. “Yeah. They open up

‘bout eight-thirty.”

“Great.” Jackson smiled at them, and I had to stuff my fist in my mouth to keep from laughing. He clearly was not accustomed to making small talk with bums. He looked like he was about to hit them with a sales pitch. “Do you guys know where I could get some dinner?”

“You ain’t been around long have you?” another one of the guys mumbled. I think he was missing at least half of his teeth, so it came out as a mostly jumbled mess.

“Uh, no,” said Jackson. “I just recently… sort of… had well, uh… this is new to me.”

“I’ll say,” laughed the guy who had spoken originally. “But you just missed dinner. On Wednesday it’s at the church on Maple.”

“Oh,” Jackson was clearly disappointed. I wondered if this was the longest he’d ever gone without food. “What about Thursdays? Is there food somewhere tomorrow?” The three guys looked at each other, and I thought for a minute that they might lie to him and send him on a wild soup kitchen chase, but after a pretty lengthy pause one of them offered up the truth. “Yeah, the Presbyterian Church by the docks. It’s at noon.”

“Noon. By the docks,” Jackson repeated. He was shifting nervously from foot to foot. I was sure he was tired. The guy was used to sitting in meetings all day. He’d done a lot of walking and not a lot of eating. His body was working overtime. He was still incredibly clean compared to most of the guys who were now in line, but his fancy ass jeans were starting to show a little wear, and his hair looked dirtier than usual. If he didn’t find a change of clothes soon, he would start to look homeless.

Jackson kept to himself until they opened the shelter doors. He was close to the head of the line so he had a pretty good choice of sleeping space. The building used to be a convent, so there was a long hall with dorm-like rooms on each side that could house six guys in three sets of bunk beds. There was also an open area with four rows of ten cots. I waited to see where he would go before choosing my own space. He chose a top bunk in one of the smaller rooms. It wasn’t a bad choice, but the more private rooms were often out of the view of the shelter employees, which meant that there was a higher likelihood of theft. I would be surprised if Jackson made it through the night with his jacket still in his possession.

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