Back To The Future: Why US Sportsbooks Aren’t Embracing Offshore Talent

Twenty years ago as a clerk in Costa Rica, when he was just beginning his journey into the sports betting industry, Joey Oddessa wondered if the calls would ever stop. Today in the U.S., amid the nationwide explosion of the legal sports wagering industry, he’s wondering if his phone will ever ring.

Oddessa bet with offshore books via telephone in his youth. When he was 29, he decided he didn’t just want to bet, he wanted to be on the other side of the line. So he packed up and moved to Costa Rica in 1999 in hopes of finding a steady job.

In the wake of the May 2018 Supreme Court ruling that opened the floodgates for states to legalize sports betting, Oddessa booked a one-way ticket back home, but he’s learning that going back to the U.S. from parts of the Caribbean or Central America, or “Back to the Future,” as some North American expatriates call it, isn’t so easy for some former offshore sportsbook employees. In fact some experiences may now spell a kind of scarlet letter.

Costa Rica sports betting: Cutting his teeth
In 1999, when the New York Yankees were atop the baseball world, President Bill Clinton battled impeachment and dial-up modems ruled the Internet world, Oddessa had begun his sports betting education.

“Every time I would call one of the sportsbooks, it was Americans answering the phones,” Oddessa recalled.

A few weeks after his plane touched down in Costa Rica, he landed an entry-level position and became one of them.

He walked into a scene typical of a sportsbook call center: scores of clerks manning desks topped with matching wired telephones in a 20-row room. In front of them was a desk stretching the length of a stage. The stage was large enough to fit 10 people, but usually was occupied by just three or four, the quarterbacks of the room who sat comfortably in office chairs as they reacted to the rings and information relayed by their clerks.

On his first day, Oddessa found himself in the front row answering calls to the 800 numbers he had dialed into himself just a few months prior. Being in the first row means dealing with the “whales” — big bettors who call to wager up to six figures in a single night. These calls often came from across international waters, to clerks in one of several tropical countries just north of the equator.

“If any phones in that first row or second row rang, those were the whales, they were the wise guys,” Oddessa said. “I was just learning the software and everything. They put me in the front row because I spoke good English.”

When a deep-pocketed bettor would call in, it seemed like everything else would stop, and the room would fall quiet, but for a single sound.

“What you would do if you were on one of those first rows, when you got somebody like a whale on the phone, you start snapping your fingers,” said one former line manager, who spoke freely on condition of anonymity.
“Everybody in the room would just stop.”

Clerks started out making $3 to $6 an hour, which was plenty at the time by Costa Rican standards. Pay raises were given to those promoted to the front of the room. Oddsmakers and line managers could expect around $1,500 a month, possibly $2-3K with bonuses.

“I didn’t know what real money was until I went to Costa Rica and worked offshore.”
The pay was adequate, but that’s not what Oddessa is referring to.

“I’ll never forget the very first phone call I got,” he said. “I was like ‘Holy shit. I can’t believe this.’ A guy from one of the Carolinas called and asked for a game.”

The bet was for $50K.
“Boom.”

He started snapping.

Origins of offshore sportsbooks
At a sportsbook based in San José, Costa Rica, circa 1998 throughout the early 2000s, work attire was flip-flops and shorts.

Twenty years later, those rooms are just a memory for many of the employees who originally hailed from the U.S. and Canada. As in a lot of industries, outsourcing and the internet changed various roles, rendered some obsolete, and created new ones. For some North American expatriates, the tropical sportsbook job was a brief stop along the way. For others, it became home, and in some cases, How I Met Your Mother.

Some line managers stuck around for the long haul. By the way, don’t refer to these guys as “traders.” Their parlance, contrary to what they’re dubbed in Europe and in some parts of the U.S., is “line managers.”

Of course there’s more to a sportsbook operation: it takes customer service and marketing associates, technology staff, operations managers and more. Similar jobs now populate U.S. job sites as recruiters seek applicants willing to move to states like Iowa, Mississippi and Pennsylvania — just a few of the jurisdictions to launch legal sports betting markets after the Supreme Court ruling.

There’s people in the talent pool rich with years of experience and tangible skills that fit the industry’s needs. But it turns out these experiences, because of where they occurred, may be a detriment. Even if these candidates would be valuable in a growing U.S. market, possessing the kind of talent and insight that some European bookmakers making inroads in the states do not possess.

Indeed, a stigma looms for some who worked offshore, including some that are well-respected for their on-the-job IQ. To understand why, we have to go back to where it began.

The long arm of the law

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In the mid-to-late 1990s it seemed like the sports betting industry was on the rise everywhere but the U.S. Offices fielding calls from whales — and guppies alike — weren’t limited to Costa Rica. You could find them in Antigua, Belize, the Dominican Republic — less developed countries from where going back to the U.S. and its technologies was akin to going back to the future.

The outfits in these countries were started by underground bookmakers that were once operating within the U.S., like Ron Sacco and Spiro “The Greek” Athanas — pioneers and/or criminals, depending on your point of view. However classified, the sportsbooks provided a highly demanded service to Americans that Congress had barred states from supplying through the now-defunct 1992 federal law, the Professional and Amateur Sports Protection Act (PASPA).

While bookmaking outside Nevada had long been illegal in the U.S., Congress began laying down the law and increasing legislation to curb illegal sports betting in the 1960s. As law enforcement continued its strong-arm through the 1980s, bookmakers grew tired of the challenging situation, and saw an opportunity to skirt U.S. law by setting up shop elsewhere. Many of the best bookmakers around the country began flocking offshore, but they did not escape the feds’ attention.

The bookmakers proceeded as though they were running kosher operations as reconstituted, or newly constituted, in Caribbean and Central American jurisdictions. Or at least the bookies felt that they were far enough outside prosecutorial reach. The U.S. government saw it differently. But sparked with newfound confidence, some once-underground bookies were ready to raise their flags like pirates sailing the sea.

One company operating the sportsbook BetOnSports, which was once floated on the London Stock Exchange’s Alternative Investment Market, even used the football season to go on a stadium tour. The company unabashedly advertised in the U.S. by driving their “Betmobile” — an RV with the company logo tattooed on the side — from one stadium to the next. And at major boxing events, you’d find their logo plastered in the middle of the ring. It was a middle finger to the U.S. government, which continued its contention that these companies were in violation of U.S. law.

But then a reckoning came in July of 2000, when bookmaker Jay Cohen, a United States citizen, was convicted in U.S. federal court for violating the Federal Wire Act of 1961. In United States v. Cohen, a Manhattan federal jury found him guilty of operating a sports betting business that illegally accepted bets on sporting events from Americans over the Internet and telephones. Although licensed in their respective jurisdictions, it wasn’t legal then for the sportsbooks to accept real-money wagers from bettors in the U.S., and it isn’t legal in 2019.

The matter of offshore bookmakers transacting with Americans also became an international dispute between Antigua and the United States that would eventually end up before the World Trade Organization. Antigua argued that the U.S. violated its international agreements by unequally enforcing the Interstate Horseracing Act, by virtue of targeting the offshore sportsbooks, and exempting some domestic operations. The panel tasked with adjudicating the matter sided with Antigua.

“This isn’t a case of forcing gambling on a population that has decided they don’t like it,” said Mark Mendel, a Texan involved in the Antigua-U.S. dispute, in a 2007 report in the New York Times. “This is the world’s biggest consumer and exporter of gambling services trying to prohibit a small country from developing its economy by offering these same services. And we find that deeply hypocritical.”

Hypocrisy or not, the impact of the legal entanglements was felt in Antigua.

The American Offshore Dream
It wasn’t just expats who were enjoying the warm climate, new lifestyle and opportunities. Locals filled the majority of jobs, which provided a ticket out of poverty as workers learned valuable skills in the process. In Antigua, Cohen’s bookmaking operation had been the second largest employer on the island. Following his conviction, Antigua’s internet gambling business declined from 119 operators, employing roughly 3,000 people and accounting for 10 percent of the island’s gross national product in 1999, to 29 and fewer than 500 employees in 2003.

Although the WTO ruled that the United States had acted in a manner inconsistent with its treaty obligations, Cohen remained behind bars in a federal prison that sat, ironically, in the shadow of the Las Vegas Strip.

Cohen’s bookmaking company wasn’t the only one that provided an economic boost to developing countries and those that powered the flourishing, controversial enterprises as they gained momentum. As Americans’ voracious appetite for sports betting persisted in the face of prohibition, offshore sports betting companies proliferated, and so too did the economic opportunities.

These were opportunities that, if you were looking solely in the U.S., could only be found in Nevada. Even for those willing to sweat in the Las Vegas heat, it wasn’t so easy to get your foot in the door. Jobs in the regulated sports betting industry remained scarce, as sports wagering was restricted to brick-and-mortar casinos in Sin City. The emergence of offshore sports betting presented a new opportunity for Americans who once thought a career of this kind was only a dream.

It wasn’t a hard sell. People wanted to work in the sports betting industry then, for the same reasons they do now: reasonable compensation, a competitive working environment with upward mobility, but mainly, love of sports. Unsurprisingly, most of the Americans willing to leave the mainland were young single males who had a healthy dose of ambition and a hint of rebelliousness.

Offshore bookmaking was an art, at least for the ones who did it right. The premier sportsbooks staffed with talent weren’t turning away sharp bettors, a trend that appears to be on the rise in the U.S. Rather, they welcomed them, but the action required steady handles at the wheel, and the ability to manage risk. Which often meant quiet.

“The talking would stop because the guys on stage that are going to move that number need to know what large bets are coming in, so the clerks 20 rows behind don’t take bets on the same exact game at the same exact price,” Oddessa said.

He worked up to eight shifts a week when he started his career in Costa Rica, adding doubles to his schedule whenever he had the chance.

His diligence paid off. For some shifts, he earned a spot on the stage, leading a team of clerks as he had once been led. Armed with a computer and phones in hand, the clerks took calls from wise guys in Australia, Asia and the U.S.

“We’re taking everybody in the world, anybody that could log onto a computer and pick up a phone,” Oddessa said. “There was half a dozen super sharp guys that were betting big into the office in all sports, especially when we opened the first number.”

Oddessa recalled what one of his early mentors told him. “You have to take all of them or you have to take none of them.”

Pros and Joes and stereotypes
Sharps provided valuable information. When booking their bets, Oddessa and his team would adjust accordingly, hoping to pit wise guys against each other to ensure profits for the sportsbook.

“I was working and learning from some of the smartest, most brilliant people I’ve ever met in my life,” he said.

Parlaying his experience as a collegiate wrestler with a sharp eye for numbers and the skills he had learned as a clerk and then on stage, Oddessa’s superiors eventually made him an oddsmaker, the person in charge of creating the lines. Focusing on combat sports such as boxing, mixed martial arts, judo, amateur wrestling and other fighting sports, Oddessa began making a name for himself.

As one industry insider told me, markets for many of the fights had their genesis in Oddessa’s office. Oddessa looked at fights as if he were solving a puzzle, and most of the time he could put the pieces together. His industry peers took notice.

With stops in Belize, Curacao and Montreal, Oddessa’s rising career took him around the world for nearly two decades as bookmakers who were unhappy with their hold percentages in the fighting markets turned to him for help.

“It opened my eyes,” he said. “The world is full of opportunity if you take the leap. That’s what Costa Rica and the offshore industry was for so many people.”

But coming back to the U.S. nearly two decades later, following the landmark SCOTUS decision, there was no red carpet awaiting him, and no new job lined up. An aura of lawlessness follows not just the risk-taking bookies who started offshore sites and fronted the capital, but also those who worked for them. However as they see it, their services — services that helped take sharp bets and meet the demand of U.S. sports bettors— are something to be proud of, and their acumen became respected within the states.

Professional sports bettors, often disgruntled with strict limits or outright refusals to take action at some U.S. sportsbooks, speak glowingly of offshore talent. One of the more outspoken figures is a New Jersey resident who goes by the name of Spanky. If you’re on #GamblingTwitter, you’ve seen his commentary before.

Shared a few laughs with many old friends while reminiscing on the past.

Doesn’t matter if I’m breaking bread with billionaires or drinking beer with locals. In Costa Rica, I’m at home with my peers.

The heartbeat of US sports betting remains in CR.

Till next time,
Pura Vida!

— spanky (@spanky) August 25, 2019

I caught up with Spanky to find out what he meant. He was quick to double down on his tweets, praising the talent in Costa Rica and the service he received and still receives.
“The talent pool is tremendous and many of these guys aren’t afraid to take a bet. The small limits you see in the states is a sign of lack of talent,” Spanky said. “Just because you’re the house doesn’t mean you can’t be beat. Instead of kicking out guys like me, these offshore bookmakers take my bets, but work their asses off to keep their edge.”

For pros, half the battle is finding a way to get enough money down. That task became more difficult following the passage of the Unlawful Internet Gambling Enforcement Act (UIGEA) in 2006, when respected sportsbooks and line originators like Pinnacle and Betcris raised the white flag, at least in regards to their U.S. customer base. Now to bet with Pinnacle, headquartered in Gibraltar, or Betcris in San Jose, Costa Rica, you must live outside of the U.S., or have a network of colleagues outside the states placing bets on your behalf.

The unpredictable political climates are also a threat. What if you have five figures in your account and the Costa Rican government shuts down your offshore sportsbook? Tough luck.

And like any industry, there are bad apples. There are ill-reputed sportsbook sites, like the Antigua-based MyBookie, which has been accused of voiding bets, withholding payment from winners and other shenanigans. Since it’s offshore, there’s little recourse a bettor can take. Regulatory bodies in Nevada and other states, for instance, allow for a patron-dispute process when such circumstances arise. Even absent anti-consumer practices, withdrawing money is difficult enough following the passage of UIGEA, which targets online financial transactions.

But for pro bettors like Spanky, offshore was the only place they could bet while PASPA was the law of the land; and now, as legal U.S. sportsbooks limit or turn them away in a new era, premier offshore books remain one of the few places they can get heavy action down.

Cold shoulder
According to sources, some bookmakers now operating in multiple U.S. jurisdictions will not consider candidates, under any circumstances, if offshore experience is on their resume or found to be omitted.

There may be a licensing issue, perceived or real, at play here. Regulators pay attention to someone’s employment and income history. Compliance officers at many properties will err on the side of caution, i.e., not in favor of those who have worked in a legal grey area.
In states including New Jersey and Pennsylvania, all sportsbook employees must be licensed. The level of scrutiny on the background check may also vary depending on the seniority of the position. Sources said there is no apparent black-and-white rule regarding previous experiences at offshore sportsbooks. Some regulated organizations have not expressed any trepidation about hiring qualified candidates trained outside the U.S.

As a practical matter, contrary to stereotype, offshore sportsbook employees didn’t and don’t walk down dimly lit hallways with flickering lights. There’s not a back room filled with cigar smoke and stacks of cash on the table.

“The organizations I’ve worked for are literally Fortune 500 companies that aren’t reported in Forbes,” said one industry insider, who spoke on condition of anonymity.

Other anonymous sources echoed the sentiment. The way they see it, their offshore experience was with large companies run by sharp, honest businessmen. Companies that were properly licensed in their jurisdictions, paid taxes, and legally employed thousands. There are exceptions, but most were not accessories to scams.

“Contrary to what many with special interests would want you to believe, the offshore industry was built on the shoulders of honorable and decent bookmakers,” one industry insider said. “People new to the business seem to ignore the fact that credibility and trust are at its foundation.”

To his point, the top-tier offshore books were started as credit businesses, as opposed to post-ups. That is, betting without depositing (posting up) money first. And the credit business boomed. Not because scores of patrons got stiffed — because of bets paid and good reputations made.

“Reputation is everything,” Spanky explained. “When I won, I didn’t get paid because of a binding legal contract; they paid me because of a handshake.”
It wasn’t only a handshake, though. It was in bookmakers’ self-interest to pay when customers won. Reputation was king; more trust meant more clients. More clients meant more bets. And more bets meant more profit, even if it requires paying out sharps like Spanky along the way.

Who knows? They do
“Vegas knows.”

You’ve heard your friends say it. It’s a bettor’s favorite explanation for betting lines that look too good to be true. They don’t realize it, but it’s usually not Vegas they’re referencing.

For years, NFL and college football spreads have been imported from offshore, as sharp sportsbooks like Betcris set the market.

“In the first few hours, especially early in the season, the spreads move quickly and often, and the market doesn’t normally settle until prominent offshore book Betcris posts its opening numbers,” write David Purdum and Doug Kezirian for ESPN Chalk. “Betcris is known to cater to sharp bettors and offer among the highest limits. Its influence on the market is significant, and lines and totals regularly drift toward the Betcris number.”

Mitigating its risk, Vegas often sat back to see how the line was bet offshore before putting numbers on the board. In essence, it wanted to know what Costa Rica knew. In fact, it still does.

It’s not surprising that the same people who left their homeland willing at the risk of some legal peril also wanted to write as much action as possible, even if most of it came from sharp, professional bettors.

“Take the bet, move the number, and just don’t fall asleep at the wheel,” was the motto.

Looking back at it all, it’s worth pondering if we’d still be waiting for the arrival of widespread regulated sports betting in the U.S., without the renegades that helped the offshore industry flourish.

Social change doesn’t happen overnight. However you feel about them, offshore sportsbooks kept the fire burning to create a climate hungry for a regulated, fair and competitive sports betting ecosystem in the U.S. that is now celebrated by the very pro sports leagues that once fought to uphold the ban.

Sports wagering is not new in the U.S. It’s ingrained in our culture, featuring a sense of rugged individualism and responsibility, allowing someone to dream of finding an edge to make a living while watching and betting on sports — or now, working on the other side of the counter.

Some with offshore experience have found success and landed jobs in the growing U.S. marketplace. Some guys came back to the future earlier than Oddessa. But in any case, successful moves into the U.S. industry is a good sign for those still looking to get a foot in the door.

“It’s a win for all of us,” a source said. “It’s one less barrier for us to break down and prove that we belong.”

Back in Florida, Oddessa is still waiting. But you won’t hear any excuses.

“Fair? Life’s not fair. That’s just the way it is,” Oddessa said.

After all, his life’s work is bookmaking and sports, in which upsets and injustices are part of the game.

| Title: Back To The Future: Why US Sportsbooks Aren’t Embracing Offshore Talent
| Author: Matt Schmitto
| Date: Jan 6, 2020