Degenerate Gambler: 'The wins just kept coming'

When normal people decide to travel to Las Vegas, the gambling usually begins after they get off the plane and check into a nice hotel. For a guy like me, though, the rolling of dice started long before I stepped on the casino floor.

In the fall of 2007 my foursome won a regional qualifier and were handed an all expenses paid trip to Sin City to compete in the Playboy Golf Scramble. While the rest of my team basked in glory and lamented about the excursion, my mind wandered to a dark place.

Visions of inserting myself into a large piece of luggage near the Seattle border and hearing the sound of a trunk slam down on me clouded my thoughts. Some legal mumbo jumbo from my past that would cause issues at the border was throwing a monkey wrench into my celebration.

There was only one logical thing to do about the impasse. I emptied my hockey gear all over the basement floor and told my brother to drive me across the border - literally.

Not many things are more helpless and humiliating than being smuggled into a foreign land inside a stinky sack, but I have a talent for allowing myself to sink to levels the average man can’t comprehend.

After successfully gaining entry I popped out of the compartment like a young Luke Skywalker exiting the belly of a fallen ton ton. My lungs quickly filled with precious United States oxygen.

I considered this personal victory my first winning wager.

A one way ticket from Seattle to Las Vegas had me checking into Treasure Island and reuniting with my team within a couple hours.

The golf was good, the Playmates were great, but the gambling was sensational.

Three days of sun coated my skin with a Côte D'Azur tan and three nights of hitting, splitting and doubling down found me 12 grand richer.

The profits afforded me a freedom not known to many degenerates. For a small period in time all doors were open.

I took the tram to the Mirage to experience Cirque de Soliel's presentation of the Beatles’ Love.

The next night I got a taste of anarchy when the pirates invaded the MGM Grand for a Jimmy Buffet concert. I capped my week by spending a few hours with Elton John and his Little Red Piano at Caesers.

My human trafficking experience was a one time deal so I decided to try and see as much as I could before making an exit. I left Vegas in an exotic rental and blew through the Mojave desert en route to L.A.

The Sunset Strip rewarded me with fine establishments like the 7th Vail and Crazy Girls where I threw my profits around like confetti while baptizing single mothers of all shapes and sizes with charitable donations.

I travelled the California coast and spent the day frolicking along the fairways of Pebble Beach before continuing my journey through Santa Cruz and on to San Francisco.

I placed my bets online Sunday morning from the hotel and settled in for some action. I took the Browns over St. Louis in the early game and the Bills over the Jets in the late.

By the time I finished breakfast, Cleveland was down 14 points and I accepted that my luck had finally run out. I couldn’t stomach watching the game any longer so I drove to the corner of Haight and Ashbury to pay my respects to the Grateful Dead, went for a walk around the Bay which showcased the infamous Alcatraz Penetintary, and arrived back at the hotel just in time to see the Browns cover the spread by returning a Marc Bulger interception for a last minute touchdown.

Cash, not gas, was fueling this road trip. The wins just kept coming.

Suddenly, it was all worth it.

The Bills later paid me a handsome reward and I reinvested a nice chunk of the profits on the Red Sox later that night as they swept the Colorado Rockies in the final game of the World Series.

My vacation turned into a scene from Brewsters Millions where I just couldn’t spend the cash faster than I was making it. My love for this addict

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Posted by eprieto2
4 years ago

"My love for this addiction allows me to reflect on these journeys and these wagers like former lovers that have had a profound impact on my soul." This is so true what gambler doesn't recall the incredible runs they've gone on, and imagine that it should be like that every time. My personal favorite was being stuck in Vegas with nothing more than $10. Winning three 2 team parlays in a row and then turning that $250 into $5,000 at blackjack. I went from not knowing how I was going to get home, to taking a limo to the airport. I wish you would write a monthly article DG. Thanks for the read.
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Posted by agentino
5 years ago

Hey DG, Great articles. I love your vibe. Don;t be drawn in by the bellends who can neve know what it is like to experience the lows, highs and then lows again. Keep em coming Denis
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Posted by surferjohn
5 years ago

Winning days like that is what keeps us coming back!!!Everything you touch turns into gold ;-)..
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Posted by bodio
5 years ago

cool story
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Posted by the_DG
5 years ago

I love to hear about your win JTC...nothing lingers longer than victory.. Hey spivince...i know it hurts your self essteen to aknowledge that this is fact..but this is true..sometimes i cant believe it myself.. My team finished 4th overall in the Playboy Scramble...-13 day 1..-15 day 2 = -28..it was held at the 36 hole Angel- Mountain Golf course..our pictures may still be on their website??..the top 5 teams recieved an invitation the the Playboy mansion and our team was honored at the Banquet I have the ticket stubs for the concerts..i have the pics of the event I played 27 holes at Spy Glass Hill for the twilight rate of 187.00 and they let me play until i ran out of light..i got my picture taken with the US open trophey which they keep in the pro shop at Pebble Beach in a thick glassed cube I rented an SUV from Avis car rental at the Venetian..they offered one way drop off..i drove it from Vegas to the San Fran and returned it at the airport before boarding a flight for Seattle I ran out of gas in Pescadero and had to hitch hike up to Half Moon Bay and paid the boyfriend of the girl who worked in the gas station 100 bucks to drive me back to my truck with a jerry can of gas I watched the Bills game from the 49 er lounge I watched the Red Sox sweep the Rockies from a bar called Chillies across from the Supersonics Stadium My brother met me at the bar and we watched the baseball game together and we drove across the border with me in the passenger seat without issue.. Sadly this article is 100 percent true It is kind of amazing i guess?
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Posted by spivince
5 years ago

Quit lying and believing ur own lies! Ur an idiot
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Posted by Philly215
5 years ago

Another good read from the DG, keep em coming man I gotta have something to get me through the work day.
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Posted by djspurlz
5 years ago

Loved the story - always great reads DG - please keep them coming - glad you went home with plus money
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Posted by RyanRebman
5 years ago

Well, I finally read it and it isn't even that interesting of a story. The only somewhat interesting part is where he has to be snuck in via a hockey bag. Even with that, a lot of people have done something along those lines. My thing is that these stories are irrelevant and should not be the lead story on covers. KongKiller... The name is Rebman.. I don't care if you disparage me, just spell the name correctly. I at least have credibility.. you are just another covers poster who has no back up. Good Luck All.
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Posted by ShuffleList
5 years ago

Sounds like a great script for a film, but too bad Hollywood would want to end up making the character lose all their money in the end and teach all the viewers some kind of lesson that there are more important things than money.... right right.
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Posted by Sberenson
5 years ago

THATS EPIC
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Posted by KongKiller
5 years ago

Ryan Rebmen go choke on one of your 10 star plays.......loser hack
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Posted by jimmygo89
5 years ago

Your stories are always worth the read...if you have any sense of humor at all. Sorry you are such a drag Ryno...loosen up! "I popped out of the compartment like a young Luke Skywalker exiting the belly of a fallen ton ton" - classic!!
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Posted by DtotheP
5 years ago

I have a talent for allowing myself to sink to levels the average man can't comprehend. BRAVO! DG
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Posted by tabasco_cat
5 years ago

Good Story, that's pretty halarious.
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Posted by rossoneri
5 years ago

UEFA CHAMPIONS LEAGUE: Unirea Urziceni - Glasgow Rangers PICK : X (TIE GAME) Standard Liege - Olympiakos Pireus PICK: HOME (S. LIEGE) Dynamo Kiev - Inter Milan PICK: Double chance on dinamo x1 or drow no bet -dinamo good luck!!!! Forza Milan!!!!
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Posted by RyanRebman
5 years ago

I didn't even read this story, but I know this article is always long winded.. Hopefully this is the last story
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Top Response

Posted by RyanRebman
5 years ago

"I didn't even read this story, but I know this article is always long winded.. Hopefully this is the last story"