Why Gambling On Horses Is Fun:

The morning after a massive night of pretending that I am still 10% as awesome as I used to be in college, I crawled to the couch and cracked open my laptop just in time for the third race at Pimlico. Big Slim had miraculously beat me out of bed that morning so I was stuck on the shitty couch.

Not a big deal though because Big Slim has the uncanny ability to pick winners strictly based on the name of the horse. No odds necessary. Before I was done reading him the names of all the horses running in third race, he said, “I don’t know how you don’t go with Diabolical in this spot.” I then proceeded to tell him what a retard loser he was for not paying attention to all the names and all the odds.

Diabolical then proceeded to win the third race. Dagger!

Big Slim managed to pick me three consecutive winners based on the ‘Money Name Theory’ before he passed out on the couch. I tried my luck at picking the next race based on generally accepted handicapping methods that I have picked up from some pretty seedy bastards with mustaches that I’ve met in Vegas and Tunica.

My horse came in 6th out of 7 horses running. And I think the 7th horse took a break to get a BJ during the race.

I tried to go back to the Big Slim well, but when I woke him up he noticed he had a missed call from some married chick he’s been trying to bone, so he left me solo on the couch. His reasoning was something along the lines of bitches being cooler than horses, but I didn’t really get it.

Needless to say my generally accepted handicapping methods produced zero wins the rest of the day. As a nice kick in the balls, Toast managed to call me about five minutes before the Preakness asking me to put a bet in for him. He was in the NYC with our boy JB, and instead of taking them to the off-track betting site JB was supposed to be leading them to, they had ended up at a massage parlor.

Being the outstanding friend that I am, I placed Toast’s two bets of 1) Curlin to win the Preakness, and 2) Curlin and Street Sense to hit the Exacta.

They both won. And that, my friends, is why gambling on horses is fun. Where else can you help your friends win money and also toss around terms like Exacta?

How I Learned How To Buy A Horse:

The Monday after the Preakness I was viciously bored at work. Big surprise. It’s hard to stay interested when you’ve made a pact with yourself to not work while you’re at work.

I started surfing ESPN.com. On that particular Monday I found an awesome article about racehorse ownership where you can buy percentages of Racehorses through “syndicates”. The syndicates do everything for you. You are essentially a silent investor. I was immediately sold.

After some brief research, I came to the decision that Team Cool & Tough needed to own a racehorse. And that WestPoint Thoroughbreds was the least shady group to help us do it. We could buy 5% of a 250K horse if we had 25 guys throw down 500 bucks each. Here are the highlights from Team C&T’s NextRound page in reaction to buying a horse:

On The Investment:

Steve Irony: I might be in… I just cashed in [insert Steve Irony’s baby daughter’s name here… henceforth known as Lil’ Irony] college fund. I am banking on her getting a scholarship.

Maske: I have so many jokes about Lil’ Irony and scholarships they’re making my head hurt. (Many more Lil’ Irony scholarship jokes were made.)

Booth: I spoke to JK, he is in and asked if he could just give me some cash if I meet him at the Pink Pony tonight. (It was a Tuesday.)

Big Cherry: Fuck it. I’m in. This can’t be any worse than some of my Vegas decisions. I have a feeling this money is going to get me a picture of a horse that was found on Google images. (Big Cherry has made some really shitty decisions in Vegas.)

Old Balls S-Mac: horse breaders/owners are notoriously sketchy, so it will be interesting to see what the ‘interest’ for your investment really is…and just so you know, unless this thing has a shot at racing Pimlico, there is little chance i ‘pony’ up the required funds. (Old Balls S-Mac has not knocked the cobwebs off his wallet in quite some time.)

Toast: Do we really have a chance to make money at this or this just a way to say we own a horse? I am in either way. (Toast wants a cool line to drop on chicks after his divorce is finalized.)

Steve Irony: I am ready…. If this works out I have another venture for us to look into: www.spaceregistry.org. (As we’ve mentioned before, SI was a big, big fan of “Highlander: The Series”.)

On What To Name The Horse:

Toast: Is he already named or can we name him C Puncher?

Anonymous: If not C Puncher, how about Dick Knife?

On What The Horse Will Look Like:

Big Slim: I found a picture of the thoroughbred Booth wants to buy, I know he doesn’t look like much but he is a beast on the back stretch. (C Puncher is pictured to the right.)

Steve Irony: Can I put a picture of the horse on a T-Shirt? Maybe we could make a calendar. (SI has a big hard-on for shitty memorabilia.)

Old Balls S-Mac: I like Steve Irony’s idea of a calendar. We could have the coolest donkey on the block with naked bitches sitting on him and shit.

On Concerns About Upkeep:

Steve Irony: What about the upkeep? (After having several unplanned kids, SI is a bit of a worrier.)

Old Balls S-Mac: Horses are expensive yo. They eat a lot and shit a lot. Who’s gonna care for Dknife? Scoop it’s shit, feed it, brush it’s mane? Who’s gonna give him a good pull when he get’s stressed out and needs to fire the cannons??

On What To Wear To The Race:

JB: I’d love to get a horse that raced in Monmouth. And Booth could wear his jean shorts to the race and not be criticized by anyone outside of our group, seeing that’s it socially acceptable there and all. S-Mac and I could wear gold rope chains and matching UF & UM tank tops to rep FL properly.

Steve Irony: I am dusting off the Sear Sucker suit and top hat right now…

When Everyone Bought In:

Booth: All 25 shares are officially off the market. The horse is 5% ours, which means:

• Steve Irony will remain a high maintenance part of my life for the next 3-5 years.

• Candle Man’s wife will continually ask him when he is building a shed in the backyard to put the racehorse they just bought in.

• And I will have an excuse to bet on horse racing on random Tuesday afternoons. I am sending out an email with a complete list of participants.

After I Forgot To Include JB In The Email:

JB: Booth your such a fucking idiot to not include me on the email.

AND…

And that is how Team Cool & Tough got into racehorse ownership.

See you at the track.

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