Vegas And March Madness: A Tradition Like No Other

About eight years ago, I sent out an email to a few guys who had gone to school with me. It was a message that would change the course of history (for me anyway) and carve out one weekend a year where I could escape my obligations and responsibilities. Many of you know this email, because you once sent it yourself.

The email made the ludicrous suggestion that my buddies and I keep in contact by doing March Madness in Vegas. Who knows, we might even make a tradition of it. I never expected my friends to go for it. For the ones that were relatively local, these were the same guys that I couldn't bribe to get together for a pick-up football game or a poker night. We had jobs that wanted our undivided attention and I was sure that some would respond that their wives or girlfriends wanted to know why it was an all-guys trip (the answer being so that we can have an entire weekend without questions like that one). Yet, to my utter shock, the yes responses kept coming in, and a few months later, eight of us flew into Vegas for 72 hours of being up all night and gambling on 654 basketball games at the same time.

This will be our ninth annual trip. A few of the names have changed-although our core four people go every year without fail. We all have wives. We all have kids or are about to. We've all slowed down a little bit. I can tell we've all slowed down because the itinerary has also changed. I made one important change after year one: four nights instead of three. You can't try to squeeze Vegas or you'll be exhausted and it will be over before you know it; and, if you have kids and you try to pull the "wow, honey Vegas really wore me out" card on your wife when you get home, you'll be sleeping on the couch until your next Vegas trip-if you get to go again.

We also made a second change around year three or four that shows our age a bit: that year, we were forced to go during the second weekend, and discovered that we liked it even better; a little less crowded, a little less craziness to our Madness.

So, on Wednesday, March 24th, I will make my annual pilgrimage. And it really is a pilgrimage. Actually, Vegas is less of a city than it is a cult. You ever try to talk to someone who's been to Vegas a couple of times without getting unwanted advice on everything? I rarely go to Vegas more than the once a year, yet I feel like I know the Strip like the back of my hand: every hotel, every restaurant. Speaking of restaurants, yes, Vegas is all about gambling, the lights, the glitz, the people watching, and of course during March, the basketball. At the same time, if you ignore the fact that you have access to about three dozen of the world's top restaurants on the same block, you're out of your mind.

In fact, for our Vegas trip, everything revolves around the food. Vegas is the ultimate cruise-ship experience. One guy wants to watch basketball, one wants to play blackjack, another one wants to go to the spa, another is a poker player? It's all good. Our reservation is at 8pm. Just don't be late.

Now, some of you might be thinking that I've gone a little soft. And yes, I have. I pace myself. That first morning I wake up early and go to the Bellagio spa, get some cucumber water, and soak in the Jacuzzi and take a deep breath confirming that I am indeed on vacation. I get a massage and then while still in my robe, I walk out onto the spa balcony eating an orange, and I look over the people gathering by the pool as I convince myself that I am Caesar and these are my subjects. I get dressed slowly before heading down to the Venetian poker tournament (placing a few basketball bets on the way) with the hope that I will finish in the money just before we are due at Prime Steakhouse that evening. I typically go to bed by (gasp) 2 am, and I come home on Sunday refreshed and relaxed-for at least a day or two.

That being said, there is little that can match the thrill of winning a big, or even a little March Madness parlay. I've spent more energy and care cheering on a $50 money-line bet on a 12-seed than I ever have on any poker hand in my life. Betting on the tourney can bring out the best and the worst emotions in us. As for the best, as one of my friends who had never placed a bet before year one naively said (with the exuberance of a small child): "Gambling makes everything better!"

However, there is definitely a dark side. After two years in a row of screwing me in the worst possible gut-wrenching ways, I went six years before I could hear the word "Wisconsin" and not want to punch someone.

I've also had bad losses where I didn't blame the team at all, but rather blamed my own stupidity. Worst karma mistake I've ever made: March 26, 2005. A nice-sized bet on the three-seed Arizona Wildcats to win outright against #1 Illinois and go to the Final Four. Arizona is up by 15 with just under four minutes left to play. I'm in the sports book, screaming my head off. And that's when it happened. My friend calls my cell phone. First off, let me digress by saying that the following should be the number one reason for not allowing cell phones in sports books, as opposed to any illicit activity. . . . He says: "I'm in the hotel room. Are you watching this?" I respond: "Yes! I'm in the sports book. Come . . . down . . . and . . . [in the movie, this would be in slow motion] . . . celebraaaaate . . . withhhhh . . . meeeeeee."

Oh, no.

I hung up the phone as quick as I could. No one could be that much of an idiot. I literally started yelling out, "who wants to buy an Arizona to win bet from me?" Alas, no takers. Three minutes later, the game went into an overtime that Illinois would win-by one point just to taunt me. It's probably around that time that I started playing more poker during these trips and betting on fewer basketball games. At least I can't screw up the lives of a bunch of college kids that way.

So, for those of you heading to your first of what may become many annual pilgrimages, I offer just a few bits of advice. Pace yourself and remember you are on vacation. Spread your gambling around: diversity is the key to any good investment portfolio. Bet some underdogs straight up and also bet some over-unders, since those bets are, by far, the most fun. Use any and all winnings to splurge on the amazing restaurants. And, above all else, don't ever, ever, claim victory before the final buzzer. If I didn't, we might all be thinking back to that gutsy 2005 Championship team from the great state of Arizona.

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