The Billionaire Bum

“Shut up, man. Just tell me you’ll do it.”

“Yeah,” he said, “I’ll babysit him for you, but you’re paying me for the whole week even if he quits early.”

“Sure thing. Thanks, Ben.” I flipped my phone shut and put my head in my hands.

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.

Jackson

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.

I balled up my jacket and slipped it under my head as a makeshift pillow. It wouldn’t be the best night’s sleep I’d ever had, but I probably would get some sleep, and that was good enough for now.

Chapter 3: Morning Dawns on a Man for Hire

Jackson

“Wake up, sir.”

“What?” I mumbled, shielding my eyes from the blinding fluorescent light. Where the hell am I?

“I need to see your boarding pass and driver’s license.” A police officer? No, he was a security guard. Airport security. I wondered how long I’d been asleep.

“Oh, I’m sorry,” I mumbled, trying to shake off the sleep. “I um…” I didn’t have a boarding pass. I wasn’t flying anywhere. I was camping out in the airport because of some stupid-ass bet I’d made with my brother. How many beers did I have before agreeing to this?

“I haven’t checked-in for my flight yet,” I said, stupidly. “Could you tell me what time it is?”

“It’s almost four a.m.,” he said. “You can’t stay here without a boarding pass. Check-in for your flight and go through security. You can sleep at the gates but not out here.”

“Oh,” I said. “Yeah, my flight leaves in about two hours anyway, I guess. So I’ll go do that now.” He looked at my doubtfully but didn’t press any further.

Barely three hours of sleep.

I ducked into the bathroom to wash my face. Getting a toothbrush was definitely on the agenda for today. My hair was a disheveled mess, even more so than usual, and I had developed a kink in my neck from the uncomfortable sleeping position. It would be dark for at least two more hours. What on earth was I going to do until morning? I clearly couldn’t stay here, as I’d just lied to the security guard.

Leaving the bathroom, I walked down to the subway platform. The cold night air crept in here, and the cement tunnel felt eerily deserted. I sat on one of the cold wooden benches and waited for the train.

I wanted a cigarette.

I hadn’t smoked since college, and even then, I only smoked when I drank. Funny how being awake at four in the morning gave me that craving.

Eight minutes later the subway screeched to a stop, and I climbed aboard the empty car. I chose a seat in the back corner and laid my head against the window. This train was on a loop from the airport to downtown. I’d taken it occasionally when I was traveling without a lot of luggage. I preferred to leave my cars in the garage at home where I knew that they’d be safe.

Who knows what could happen to a car left unattended in the airport parking lot?

Supposedly, the train would just continue to make the loop every forty minutes or so, twenty-four hours a day. There wasn’t a lot of traffic going to and from the airport right now, so I thought my seat would remain mostly unoccupied with the possible exception of the four downtown stops. I knew it wouldn’t be great, but my body was not ready to give up on sleep yet, and I didn’t want to wander the streets until daylight. If I made the loop three times, it should get me through until morning.

Knowing that I would need to make better arrangements for tonight, I began to put a list together in my head. First things first, I would find a job. I was not a lazy homeless bum. I would work my way into a better sleeping place for tonight.

I knew that I’d have to find someone who would pay me a daily. If I had to wait a week for my first paycheck, the whole thing would be a moot point. Surely, someone would need day labor.

I slept fitfully. The first loop was all right, but as it grew closer to morning the subway became more and more crowded and sleep became less possible. It was difficult to keep track of time in an underground world, but I finally decided to make my exit when I could see the daylight filtering down the stairwell at one of the stops.

Wearily, I left my seat and climbed out into the heart of downtown. It was raining... of course. I reminded myself that it could have been worse; it could have been snow. I hoped that I wouldn’t get too soaked.