The Billionaire Bum

By: Samantha Blair

Shel would probably kick my ass when she found out what I’d done. Jackson had totally gone off the deep end on me. I know the stupid bet was my idea, but I didn’t actually expect him to take me up on it. Dude clearly had no sense of self-preservation. He’d be lucky to not get his ass killed in the first twenty-four hours.

I called Ben as soon as I got home. Someone had to watch him to make sure that he didn’t really get into too much trouble. Ben and I had played college football together; he was almost as big as I was. We’d stayed in touch periodically, and I knew that he was still in the area.

Ben worked in the security business as a personal bodyguard and had more common sense than most people. I knew that he wouldn’t let anything really bad happen to my brother.

Jackson had almost seventy dollars on him when I left him, and he’d just eaten, so he wouldn’t starve over night. I just hoped that he wouldn’t get himself shot or beaten to death. This was a pretty safe city, all things considered, but he wasn’t exactly the picture of street smart. A real learning experience was coming his way.

One night on the streets might even be good for him—teach him a little humility. I’d be the first to admit that we were both born with silver spoons in our mouths. I’m not sure that Jackson ever really understood how blessed we were. As much as I loved my brother, I could admit that he had a sense of entitlement about him that had always bugged me. Grades, money, women—everything came easily for him. He hadn’t been told no very often in his life, but that was all right. He was amazing at his job, and for the most part I thought he was pretty happy with life, but there were times, like last night, when I thought he’d really lost touch with the world. He could get so caught up in the stressful details of his own shit that he missed the big picture completely.

Who was I to judge, though? I could be like that, too. Thank you, God, for sending me Shelby. That woman had a way of grounding me and setting my ass straight. Jackson needed a woman like that.


What the hell am I going to do now?

I really hadn’t thought this through the whole way. If I had, I probably would have insisted on waiting until morning to start this ridiculous charade. I could have had one more good night’s sleep in my own bed. I also would have dressed a little more appropriately. As it was, I was wearing designer jeans, a plain grey t-shirt, and light spring jacket. At least I changed out of my suit. I wasn’t exactly planning on tenting out for the week.

First order of business: find a place to bed down for the night.

I ran a list of possibilities through my head. I knew that this city had homeless shelters somewhere, but of course I had no idea where they might be, and I couldn’t Google it because Jason took my iPhone. The thought of a shelter didn’t really appeal to me anyway, but it was better than staying outside. It still got pretty cold at night in the spring. Of course, the doorman for my own building knew me. I owned the whole place and paid his salary. I could get into my penthouse apartment without my keys, if I really wanted to, but I was no cheater, and I had a feeling that Jason would find out somehow if I did go home.

Could I find a hotel cheap enough? That was probably a bad idea. I needed to put myself on a budget. I had about ten dollars a day if I wanted to last the week. A hotel that cost less than fifty bucks a night wasn’t exactly my idea of fun anyway.

So that left public places where you could sleep without being noticed or bothered. The subway was good thought. I knew I’d seen homeless people camped out there. It was still cold though, and I was hoping for somewhere warmer. The airport? I didn’t have any luggage, but I was well enough dressed with my three hundred dollar shoes, and I thought I could pass for a traveler waiting for an early morning transfer. No one brought carry-on luggage anymore anyway, right? It was too much of a security pain.

That seemed like the best idea. I’d come up with a better plan for tomorrow night, but it was already creeping up on midnight, and I was ready to lie down for a while.

It was only about twenty minutes to the airport by subway and the trip passed quickly despite my dislike of public transportation. The ticket cost eight dollars, but it was good for three days anywhere on the whole subway system. I had a feeling that mobility might be important in this game.

The airport was pretty dead this time of night. Most of the shops and restaurants were closed and only a small handful of employees were left at the ticket counters checking-in late night passengers. I found a vacant set of three chairs linked together in the hallway around the corner from the United Airlines check-in counter. The bathrooms were right across the hall, and I was just out of sight of the security line. Perfect.

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