Life Experience of a Bookmaker in Costa Rica

After a few years of acclimating to Costa Rican culture I applied for a customer service job at an English speaking company. Little did I know, I was about to take on a job that would change my life forever. This wasn’t your ordinary CS job. The position was for a customer service clerk at an offshore gambling facility. The money was good and I would be speaking my native language all day. What more could I ask for?!?!?

Online gambling was at it’s prime and this was not your average “bookie joint”. This particular betting outlet was setup like a true business.    Complete with a customer service department, a sales department, and a betting department. With US 1-800 numbers directed to our phone system they were ready to take on the United States market. I am truly grateful to have found this job. The customer service and sales training that I had received would later prove to be a great asset in my current career.

After working there for about three years I quit and job hopped for a couple more years. While working at a gambling software company I met one of the most influential people in my life, me ex-employer. He offered me a job as a customer service/betting clerk while making urinal small talk. I kindly denied because of my work ethic and wanting to be faithful to the job I had at the moment. They laid me off about a month later because they were going out of business. Go figure! I was now unemployed and had recently turned down a seemingly good opportunity.  As being without a job for about two months started to take it’s tole I heard through the grapevine that the guy I had shared a urinating moment with was trying to track me down. Needless to say i got in contact with him and was given the job.

This job would later lead me to some of the craziest experiences anyone can ever imagine. I became the right hand man of a Los Angeles old school bookie. When I started at the company there were only four of us. After some negotiations and lots of drinks we sealed a deal with several bookies located in the New York area. The deal consisted of us processing their customers’ bets and handling all of the data entry in Costa Rica in exchange for a weekly fee per customer. This caused our business to grow exponentially in the matter of a few months. We went from having four employees to having over one hundred and thirty total employees. I was soon promoted to manager of the company and would be overseeing the day to day activity as well as entertain new and existing customers.

I soon found myself partying with entertaining customers on the streets of Costa Rica on a weekly basis. Although this was SO much fun it can start to take it’s tole. (I will touch on my partying entertaining memoirs on another post so stay tuned. If you have ever seen shows like the Sopranos or movies like Casino and Good Fellas you will have a pretty good idea of the people I would be dealing with. It was never really hard to remember names of the guys from the east coast because they were either Anthony, Stevie, Joey, Tony or any other of the Italian mobster names.

The one drawback of conducting “grey area” business in another country is getting paid. All money transactions were handled here in the United States and it was not as simple as making a deposit or sending a bank-wire since the funds were gambling related. As many of you may already know, gambling is frowned upon here in the United States unless you are in Las Vegas. The solution was simple. Send someone to meet the “fellas” in New York every two months to collect payment. That person would then fly back with the money. Just to clarify. We are not talking grocery money. I am talking about pick ups of $100,000.00 CASH. The person designated to do the pick up would get a kick back of 5% of whatever was brought back safely to Costa Rica. That’s $5000 per delivery!!

I of course volunteered several times to do the pick up since I already had a good standing relationship with the “fellas” in New York. After several successful missions I decided to do a small $40,000 pick up in Denver while on vacation with my wife ex-wife. Everything was great until our direct flight from Denver to Costa Rica was canceled and we had to reschedule a flight with a layover in Houston.

We were awaiting the arrival of the plane when I received a call from my boss. “Did you make it through the checkpoint?”. I responded with a cheerful “You bet!”. Everything seemed to be A OK. Our plane arrived and it was boarding time. As we approached the jet way I noticed several homeland security officers doing their rounds with a dog. I turned to my wife ex-wife and said: “Wow I feel so much better knowing that they have dogs looking for bombs before we get on this plane.”. We proceeded down the jet way towards the entrance of the plane. As I am walking by the homeland security officer that had the K-9 I feel the dog bite my right leg and assume the “sit” position. I looked back at the officer and he told me to  keep walking. Mind you I had the lump sum of the funds in my right hand cargo pants pocket. I was even wearing a pair of baggy sweats over my cargos. At the same moment I hear the officer yell out to the other agent who was by the door of the plane “CODE GREEN”. I thought nothing of it and kept on my way to the plane. When I arrived at the door I was confronted by a female homeland security agent. She says to me: “Hi Sir. How much money are your carrying with you today?”. I respond with:”Oh…nine hundred or so…”. She then made me sign a paper stating I was carrying only $900 cash. I gladly signed and asked if I could be on my merry way. The answer was: “No. Please step over here and empty your pockets.”. I emptied my pockets and stupidly thought I still had a chance to get out of this one until they brought the dog back over. The dog went straight for my right leg again. I was asked to empty “THAT” pocket. I emptied my pockets by the wads of $5000. In the matter of seconds I came up with a credible story. I told the agents I had no idea I had to report the funds. When asked where I got the money I told them I was playing poker at a private game in Colorado. (I have never played poker in my life!! But they didn’t need to know that :)) My wife ex-wife and I were escorted to a cold back room for interrogation. After several hours of questioning they decided to confiscate all of the money. I was given $300 of the $40,000 to get a hotel that night and a taxi back to the airport to catch next flight out.

Who would have ever thought that they have money detecting dogs. I mean come on!!!! You can only imagine the phone call of shame that I had to place to my boss informing him of the mishap. He wanted to reach through the phone and strangle me :(. The next day when we arrived in Costa Rica he was not all convinced that money sniffing dogs exist. He figured I had dropped the ball at some point in time which lead the officers to me. Not to mention the unspoken thoughts that he had of me pocketing the money and making up an elaborate story.  I did my due research and showed him videos on youtube of these dogs that were trained to sniff out large amounts of cash. He eventually got over it and told me that if I wanted to challenge the claim and get the money back I could keep it for myself.

I hired a lawyer but ended up NOT claiming the money. I didn’t want my name further involved in any talks of money laundering. In case you are wondering I did go back for a few more pick-ups but I made sure to keep it under $10,000 at any given time.

Fast-forwarding a couple years I now have a “square” nine to five job in the US and I love it!!!


3 thoughts on “Life Experience of a Bookmaker in Costa Rica

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