My Mom would kill me if she knew I put $1000 on red at a roulette table. Oh, wait, she reads this site. Hi Mom! Guess what I did this weekend?

Since a few coworkers and I have been at our company for more than four years now, we're all fully vested. What's the best way to celebrate being fully vested? Why, blowing all that hard-earned cash in Vegas, of course!

Disclaimer: I'm not much of a gambler. In fact, the most I've ever won in Vegas is negative-twenty-bucks. The working assumption under which I act is: the cash I bring to Vegas will be the cash I lose in Vegas. And so far, I haven't been wrong.

Two hours before we had to check out of the hotel and catch our plane, I was $1000 in the hole. I was in better shape than my friends, but still, that's a big chunk of money.

My mind raced. What could I do to win back that $1000 easily and quickly?

I think it was a combination of things that lead me to the answer. First, there was the alcohol. I had a Bloody Mary that morning and the dull taste of stale scotch still lingered in my mouth from the night before. Next, there was the lack of sleep. I'm sure I had more sleep than most people, but four hours of winks isn't nearly enough for my old bones.

Finally, there was the sheer stupidity of my brain. Because, only a stupid brain could honestly ask a question like: "What could I do to win back that $1000 easily and quickly?" with a straight face.

By now, you know the answer already. My stupid, tired, drunken brain told me the answer was… roulette!

I approached the table with a mixture of adrenalin, anticipation, and sweaty palms. Also: a $1000 bulge in my pocket. (Now how's that for a pick-up line?)

I looked the dealer in the eyes, whipped out my money clip, and threw ten $100 bills onto red. The dealer grinned and spun the ball. My eyes locked onto that tiny ball as it spun and spun and spun… and finally, it landed on…

…well, before I get there, let me tell you how this weekend started. Right after we dropped off our stuff in the hotel room, we prepared ourselves with a glass of 30yo Macallan Scotch Whisky each. Then we strolled into the High-Limit Slots area to blow a quick wad. Of money, I mean.

While a friend sat down at a $100 slot machine, I opted for a $25 machine. After two simple pulls, I made $1175. Not bad for the first hour in Vegas, huh?

Now back to the roulette game. As it spun, another player looked up at me with a smile. "I'm rooting for red for you, man!" he cheered. I kissed my empty money clip, touched it to my forehead, shoulders, and chest, and uttered a silent prayer. The dealer chuckled and nodded. And finally, it landed on…

…oh, let me tell you about my great new gambling strategy. Each time I sat down at a new game, I allotted only $200 to play. If I lost it all, I'd stop playing and move on to another game (or stop playing for a while). If I won more, I'd stop playing and leave with my winnings. It's a prudent and conservative strategy that saved me from losing mucho dinero.

And in direct conflict to this prudent and conservative strategy was my other great new gambling strategy. I only played when I began to "feel" it. If I didn't "feel" it, then I'd get a drink or watch my friends play. "It" being the vibe, the warm tinglies in my gut, the sense of being a Winna!

This novel strategy was applied liberally to games of lower odds, like slots and roulette. Why? Well, remember what I was saying about my stupid, tired, drunken brain? Good.

For instance, I occasionally would get a very strong sense of "Red red red!" Whenever that feeling hit me, I'd look at the roulette table and pretend to bet on red. And what would win? Red! Same for "Black black black!"

I only pretended to bet because, at the time, my confidence level in roulette was still pretty low. These pretend bets served to hone my "feeling" to be more, uh, accurate. Um, yea.

So if I was "feeling" the right colors, I should play them, right? Right. Now let's get back to the roulette game in progress.

As it spun, I reflected back on my entire weekend of excess, greed, and gluttony. What have I become, I asked myself. Here I was, throwing away $1000 in hard-earned cash. Because of what? A "feeling"? Some little voice inside my head? I worked hard for this money. Now I was gambling it all away. What the hell was I doing??

Fear and grief began to creep into my stupid, tired, drunken brain. I began to regret dropping that much money onto the table. There was nothing I could do though; it was too late to take it back now.

I tried to turn away from watching the ball, but couldn't because, hey, we all love a good car wreck, right?

And finally, it landed on…

…on…

…on…

…don't you love suspense…

…on…

…Red!

Holy shit I won! I just won a thousand friggin' dollars!! Gambling rules! That little voice in my head rules! My new gambling strategy rules! $1000! Woooooo!!

Whew! That was too easy. I've broken even. I won back that $1000 easily and quickly. What do I do with all this money now? Let it ride? Hmmm.

Don't worry Mom, I didn't gamble anymore. I put it into my pocket and didn't take it out again until I was at the bank to deposit it.

But still… I could be depositing double that right now. Because after I won that round, I had the "feeling" again.

"Red red red!" Which must mean that red is another Winna!

. . .

What's the most you've gambled?