It was 10:30 AM on a sunny winter morning. Looking for a break, I bundled up and walked up to the convenience store to buy my lottery ticket. Now, I know what you’re thinking. I’ve heard it before. “Lotteries are a tax on people who don’t understand math.” It’s true. And especially for those who don’t understand the branch of math known as probability. If you spend money on tickets while thinking, “I’m gonna win,” you’ve already lost.

But that’s not how I buy lottery tickets. For me, they’re a form of entertainment. My wife loves to go to concerts and plays and movies as her form of entertainment. She easily spends hundreds of dollars per year. She gets charged up in crowds. Me? I get drained by being in crowds. I’ll do it occasionally, mind you. I go to some of the concerts, plays, and movies with her. While I do it, I’m often thinking I could be home working. So, how does a workaholic with an aversion to crowds let off steam and recharge? Daydreams. I can spend a buck or two on a ticket and then take a 10-minute break every few hours to imagine how my life would change if I won. Usually, it comes down to, who would I give the money to? I like what I do. I wouldn’t stop doing it just because I won a lottery. Still, my church could use a bit more and there are a few non-profits I would support, and I might set up something for my nieces and nephews, although that is less likely. The older ones have never done anything to contact me. I send them presents, and what do I get? A thank you note? Nope. Forget about them.

For the little one-state lotto, it’s one buck, and is drawn twice per week. If I buy a ticket for every drawing, it’s no more than $104 per year. There are also the two big multi-state lotteries. These days, their tickets are up to $2. Again, even figure that I bought all three for every drawing, it comes out to $510, which is still a bit less than my wife pays for her types of entertainment tickets in a year. Of course, I don’t buy a ticket every time. I only bother with the big ones when they get above a quarter billion for the grand prize. That is worth paying a couple bucks to dream about. Of course, I’ll pay $1 for the state lotto to dream about what I’d do with a prize that’s usually between one and two million. Go figure. As I said earlier, it’s not about the math. It’s about the dreams.

I work from home and walk to the convenience store to get my tickets. It’s less than half a mile away. As I came into their lot, I saw two vehicles there. There was the store owner’s black Jag and a limo that appeared to be private with the chauffeur in the front. That was it. It was between the morning rush and the lunch rush, which was exactly how I timed it to be. As I walked in, the owner was talking with an old guy who seemed to be looking at the liquor behind the counter.

“Get me a bottle of cinnamon schnapps,” he said as he pointed.

“Certainly, certainly,” the owner reached back and grabbed the bottle and started ringing it up.

They were at the right-hand register. I bellied up to the counter at the left-hand register. They have lottery information posted there. The really big multi-state lottery was up over a quarter billion. It had also been so on the last drawing, and nobody had won the grand prize. I had bought a ticket for it the Wednesday before, and it had been a $4 winner. I knew all this, of course, but I had to look at the list to get the names right. I’ve been playing these games for years, and every once in awhile, they change the games and the names to something new. Unfortunately, the old names are still in my head. Every time I go in, I have to look at the list to get the names right. Otherwise, I might ask for “The Big Game” or “Lotto*America” or another game that has gone the way of the dodo.

The boss finished selling the other guy the booze and came over to me, “You have decided to come back to us!”

He seems to think if he doesn’t see me for a few months that I’m not coming in, as if he didn’t have employees who worked the evening shifts. I handed him the $4 winner, “It’s only been two days, Sridar.”

“Oh, you got this here? We gave you a winner? It must have been a mistake. I’ll do better this time.”

“Thanks. I appreciate your vote of confidence. Get me one of the state and one of the really big one.”

“Don’t bother with the really big one,” the other customer said as he cracked open his bottle and took a swig.

“Beg pardon?” I asked.

“Look, kid, if you win the little one, you’ve got some spare change in your pocket, you know? But you go on with life. But winning the grand prize on the big one? That will mess up your whole life.”

“Oh, really?”

“I could tell you stories, kid.”

“Are you a bankruptcy lawyer? I’ve heard a lot of folks who win lotteries wind up going bankrupt.”

“Nah,” he shook his head and took another swig, “I’m an artist, but I won the big one several years back when they first started the multi-state ones. It was the biggest pot ever up to that point.”

The owner handed me my two tickets and the dollar in change from my $4 winner.

“Well, too late. I have the ticket now. I guess I’ll have to deal with it if I win,” I gave the old guy a smile and stuffed the tickets and dollar bill into my inside coat pocket. I went back out into the cold sunshine with the old guy right behind me.

“Is that your Jag?” he asked.

“No, it’s his,” I nodded back at the building to indicate the owner.

He looked around the parking lot, “Well, where are your wheels?”

“I walked here.”

“How about if I give you a lift?” he gestured at the limo.

“You got three blondes and a redhead in there?” I made as if trying to see through the dark windows in the back.

“No, nothing like that. Truth to tell, I’d just like to talk to someone, someone who isn’t an employee,” he gestured at the chauffeur, “and someone who doesn’t owe me anything. I don’t have anyone like that in my life.”

I may be foolish, but I think I have a pretty good read on people. The old guy didn’t seem like a serial killer. He seemed like a lonely old man who wanted to talk.

I shrugged, “Sure. Don’t know how much talking we’ll get done driving two blocks, though.”

“I’ll throw in lunch at the Trumpeter, if you’d like.” The Trumpeter is an upscale restaurant nearby, although pretty casual in atmosphere. Personally, I’m too cheap to spend that much on food. I’m a simple man with simple tastes. My car is a quarter of a century old, mainly because I can’t see investing in a newer car when this one is still running and treating me well. Go out to an expensive restaurant? Not something I’d pay for, but if offered in exchange for listening to an old man talk, I’m no fool.

I laughed, “You’re on.”

We got into the back of the limo and he pressed a button to announce the destination, “The Trumpeter, if you please, Floyd.”

“Yes, sir,” came from the speaker. And the limo started maneuvering in the small parking lot to get pack out onto the main street.

The old guy sighed, “I’m an artist. I always wanted to be an artist. I planned it from youth, but I never wanted to be a struggling artist. Being half-starved never held any attraction for me. So, I had my first two degrees in business. After I got my MBA, I went back and got an MFA. College, even graduate degrees, were relatively cheaper when I was young. And I was working hard to pay my way through. I didn’t take out any loans. MFA is Master of Fine Arts, by the way. It’s a terminal degree that allows one to get a job teaching college in various studio arts programs around the country. Do I look like a college professor?”

“I seem to remember some pretty strange-looking ducks at the head of my college classrooms, especially for the economics courses.”

He laughed, “They were a fairly buttoned-down lot when I got my MBA, but you’re a bit younger. Things had become more casual by the time you probably went to college. They all wore suits and ties in my day. But getting back, I had a business consulting career with art on the side as I built up my practice and reputation. The consulting provided a good income and surprisingly many contacts for the art. When I was probably a bit younger than you are, I got a job teaching art at the college level and left the consulting behind.”

He took another swig from his bottle of schnapps and handed it across to me. At my hesitation, he said, “The alcohol content will kill any germs.”

Hell, I always liked anything with cinnamon, I went ahead and took a small swig and handed the bottle back. That was about when we arrived at the Trumpeter. We went in, got a table, and placed our orders before he started again.

“Teaching is good, but it can be wearing. I loved it, but after seven years, I was ready for my sabbatical. I planned to make art and enjoy the year off from students. The only problem was that there had been a downturn in the market. I wasn’t as financially secure as I had intended to be, and I had some plans for some big, expensive artworks. I started buying an occasional lottery ticket.’” He laughed, “The only problem is that I am the unluckiest man in the world.”

“If you’ll forgive my saying so, you don’t seem that unlucky to me.”

He ran a hand through his white hair, “It’s true though. Every team I root for loses, doesn’t matter the sport. Every four years, I forget and start rooting for some Presidential candidate in the primaries. It’s the kiss of death for every one of them as I move my hopes from one to the next. The last election, I got smart and declared for the candidate of the other party for the general, so my party won. My curse killed their chances the two times before that. I should have stuck with the crazy third-party I used to be with. Anyway, the universe has a great deal of spite towards my declared intentions. I occasionally remember this and use it for my benefit, but I don’t remember very often.”

“And this applies to the lottery?” I asked.

“Oh, yes,” he shook his head as if remembering a thousand regrets. “I was buying the occasional state lottery ticket. Didn’t really think I would win, but it was better than doing nothing, and it didn’t cost me much. I was never one of these guys who would blow the budget on gambling. My expectations were met pretty well. I got an occasional dollar or two back. Then they came up with this big multi-state thing. And the one that was available where I was at the time got way, way up.

“With the little state lottery, I wanted to win. A million or so? Take the cash option and pay the taxes, you might end up with a few hundred grand, you know what I mean? That’s a nice bonus. Might buy a house or pay off an existing mortgage, which changes the cashflow situation. In my case, it would have allowed a few really big and great artistic projects that sabbatical year.

“The big multi-state, though? Especially when it was up where one winner would take home eight figures after cash option and taxes? It was too much. It would give a man instant celebrity, which is the worst kind. The other thing is that you have to agree to be part of their advertising to collect your prize. With the single state lottery, you can keep your name private and out of the news. But you win the multi-state, your name gets plastered everywhere, and every financial wizard investment adviser,” he made air quotes here, “and false family member comes out of the woodwork to share in your good fortune.”

“But you bought a ticket anyway,” I said.

He nodded with a rueful smile, “With its being so high of a prize, I nearly felt obligated. I didn’t want to buy one but felt I had to. I even calculated the odds in the game. Sure, someone has to win eventually, it’s the way the game goes. It was so high that there was a huge run at all the stores. People were buying hundreds of tickets. In my calculations, I figured that there should have been at least 12 winners of that pot, if the tickets were evenly distributed across the numbers. There was no way that one person would win the whole pot, and I sure as hell didn’t want it.”

“But you won it all?” It was pretty easy to see where the story was going.

“I did. My mistake was declaring there was no way it could happen and that I didn’t even want to be one of the twelve on average. It was the same as my declaring for a Presidential candidate. Surefire disaster. Have I mentioned I am the unluckiest man in the world?”

“I can probably think of worse things that could happen to a guy.”

He shook his head, “It was bad. I had to change my phone number. I had to move. I was too busy dodging the dodgy people who suddenly showed up in my life to make any art. I finally had to legally change my name and move to another state. My career as an art professor was also done.”

“Well, in the new state under the new name, did you manage to at least pursue your art?”

“No, I tried, but the money weighed on me. The more you have, the more space it takes in your mind.”

I smiled, “I figure if I won too much, I could always give it to charity.”

“No charity believes in a one-time gift,” he said. “You give, and they come back to ask for more and more. If you give a lot, they come back with naming opportunities. ‘If you give us another million, we’ll name the new building after you.’ I did give away some, but eight figures is a lot of money. It’s a lot of work giving it away. I finally set up a foundation that had very strict rules about not contacting or soliciting. Any non-profit that does will never be considered for a grant again.

“Still, I only put about half the money into that, because it was too much work giving the whole thing away. I hatched a plan to get rid of the other half.”

I raised an eyebrow, “Was this some sort of Brewster’s Millions scheme where you’d give it away to anyone who could spend it in services?”

“No, no, nothing like that. I decided to lose it in the stock market. I have an MBA in finance, and I decided to put it to work. I started searching the various trading boards for stocks that were highly overvalued and due for a fall. I would buy a few thousand shares here and a few thousand shares there waiting for the fall. My plan was to buy high and sell low until most of the money was gone. I would leave myself enough to live comfortably and go back to creating art, knowing that I would have to re-establish a reputation under my new name. I couldn’t go back to the old name and have people track me down.”

The food came at that point, and there was a break in any conversation that didn’t involve praising the meal.

As I finally pushed my plate away, I asked, “So how did that work, with the stock market?”

He looked at me and shook his head, “Have I mentioned that I’m the unluckiest man in the world? I bought stocks that should have fallen soon, and they moved up. After a few months of gains, I would give up and sell the shares, and then they would finally drop. No matter what stupid moves I made, what stupid things I bought, they would go up until I finally would sell them. I could not lose money. I got involved in derivatives trading that should have lost me money. They never did.

“Finally, I just gave up. I bet against the whole damned thing. I created what might be called an anti-hedge fund. Instead of managing risk, it exacerbated it. With the market going as it was, it should have lost me a ton of money.”

“You’re going to tell me this was right before the big financial collapse, aren’t you?”

“It was,” he shrugged.

“Have you tried to make money on the stock market? Losing money doesn’t seem to be working for you.”

“I should have thought of that earlier,” he admitted. “It’s not natural to think of oneself as unlucky when one has a roof over one’s head and money in the bank. But at this point, it’s too late. I’m an old man, and I’m dying, and I never managed to get back to art, because I was so busy trying to lose money. I have more money than ever. I have been moving more and more into my foundation. But even the foundation’s investments are making money.”

“I guess you can’t lose for winning,” I quipped.

“I suppose so,” the old man dug out a money clip and peeled off two C-notes, one for the meal and one for the tip, “There’s no reason not to be overly generous for a man like me.”

We got back in the limousine, and he dropped me off at a corner near my home. Neither of us wanted to spoil the anonymity of our interaction. As I stepped out of the limo, he gestured to my coat where the inside pocket was that I had stuffed my tickets into and said, “Son, don’t take this the wrong way, but I certainly hope you don’t win that big lottery. I wouldn’t want it to destroy your life as it destroyed mine.”

“Thanks,” I said, “and thanks for lunch.”

I closed the door and the limo drove away.

Now, I’m sitting here looking at a ticket that the unluckiest man in the world hopes loses in the drawing tomorrow night.