Jimmy Boyd in 
Long before online sportsbooks existed, betting on sports was a mostly underground affair.
Many bettors placed wagers with local bookies operating illegally, often under the influence of organized crime.
These backroom bookmakers had questionable reliability – winning big didn’t always guarantee you’d get paid in full.
For legal bets, the only option was to head to Nevada, where sports gambling was legalized in 1949.
By the 1970s, Las Vegas had become the destination for sports betting, with gigantic casino sportsbooks and flashy odds boards.
In fact, Vegas was king until the late 1990s, when a new challenger emerged: the offshore sportsbook revolution.
Two key factors set the stage for offshore betting’s rise.
First, in 1992 the U.S. passed the Professional and Amateur Sports Protection Act (PASPA), effectively banning sports betting in all states except Nevada (and limited forms in a few others).
This meant Americans outside Nevada had no legal outlet for sports wagers, pushing demand into the shadows.
Second, technology was on the verge of changing everything – the internet was about to go mainstream, and with it, new ways to wager.
Early Offshore Sports Betting Takes Root (1980s)
Offshore sportsbooks didn’t appear overnight with the internet; their seeds were planted in the 1980s.
One early pioneer was Gary Bowman, an American bookmaker who in 1985 moved to Manchester, England and launched American Football Pools.
Armed with a British gambling license, Bowman sold NFL parlay cards by mail to U.S. customers – completely legally, since he was operating from the U.K.
This made Bowman’s business arguably the world’s first true offshore book, targeting American bettors from abroad.
It proved immensely popular, and Bowman later expanded into a full sportsbook (Bowman International) offering straight bets, teasers, and more, much like a Vegas book but across the ocean.
Around the same time, other American bookmakers saw the opportunity to relocate offshore.
Notably, veteran oddsmaker Ron “Cigar” Sacco – often dubbed “the godfather of offshore gambling” – set up shop in the Dominican Republic in the late 1980s.
Sacco had been a big-time U.S. bookie (even famously flaunting his trade on a 1992 60 Minutes segment) and he moved his operation to the Caribbean to escape U.S. law enforcement.
His Dominican operation (which later evolved into CRIS – Costa Rica International Sports) accepted bets by phone from Americans and thrived by operating in a legal gray area outside U.S. jurisdiction.
Sacco’s success showed that an offshore sportsbook could attract a large U.S. clientele—as long as it stayed offshore. (CRIS, the company he founded, is still around today as Bookmaker.eu.)
By the early 1990s, a handful of enterprising bookmakers had established themselves in places like the Dominican Republic and Antigua.
These early operations relied on telephone betting – often via toll-free numbers – and word of mouth or ads in sports magazines to reach customers.
Still, their overall numbers were small.
In fact, as late as 1994 there were fewer than ten offshore sportsbooks in operation.
But that was about to change with the advent of online wagering.
The Rise of Offshore Sportsbooks in the 1990s
The mid-1990s brought the internet boom, and offshore sportsbooks eagerly rode that wave.
At first, websites were rudimentary – mostly text-based “billboards” that listed betting lines and contact info.
You couldn’t actually place a bet online in the early years; instead, you’d still call in your wager after browsing the site.
However, this was enough to spark curiosity, and more bettors started discovering these offshore sites.
Each year in the late ’90s saw tremendous growth in the industry, as new companies sprang up in various tropical locales to meet the surging demand.
One landmark moment came on January 17, 1996, when a small company called Intertops accepted what is widely regarded as the first-ever online sports bet.
On that day, a bettor from Finland logged onto Intertops’ website and wagered $50 on a European soccer match – and won $2 when it hit.
Intertops had been founded back in 1983 by a German bookmaker (after relocating to London to escape Germany’s state gambling monopoly).
By the ’90s, under the guidance of a young manager named Simon Noble, Intertops focused on the internet as the future of betting.
Their successful 1996 bet proved it was possible to take wagers online, and soon they were doing so regularly.
Intertops even launched one of the first mobile betting sites by 2000, staying on the cutting edge.
The company eventually moved part of its operations to Antigua to take advantage of the offshore-friendly climate, but it had undeniably “opened the floodgates” for online sports betting worldwide.
Another trailblazer of the era was World Sports Exchange (WSEX), founded in 1996 by three American friends: Jay Cohen, Steve Schillinger, and Haden Ware.
Cohen and Schillinger were former traders who saw parallels between Wall Street and sports betting – they envisioned an online “sports stock exchange” with continuously moving odds.
Thanks to PASPA, they couldn’t base this business on U.S. soil, so they relocated to Antigua, which welcomed online gambling with open arms.
WSEX obtained an Antiguan license (for $25,000 a year at first) that legally allowed them to take bets from anywhere in the world.
They launched their site in November 1996, initially attracting only about 20 customers, as internet usage was still nascent.
Early on, Cohen and team spent as much time teaching customers how to use the internet as they did taking bets – they’d field calls from curious bettors and literally explain how to go buy a modem at RadioShack just to get online!
Despite those humble beginnings, WSEX caught on quickly.
By 1998, it had a couple thousand customers, and by 1999, triple that.
The site aggressively advertised in U.S. sports publications and on radio, openly flaunting its services.
WSEX’s founders saw themselves as legitimate entrepreneurs rather than outlaws – as Jay Cohen famously quipped, “If you go to our website and change ‘Boston Red Sox’ to ‘Boston Market’, we’re Ameritrade”.
In their view, they were simply providing an innovative financial-like service, filling a market need left by the U.S. betting ban.
Several other offshore books launched during the 1990s, forming the first generation of online sportsbooks.
The Greek Sportsbook (originating in Jamaica, led by Spiros “The Greek” Athanas), Bodog (started by Canadian Calvin Ayre in Costa Rica in 2000), and BetCBS/BetCRIS (Sacco’s operation, which moved to Costa Rica and rebranded as Costa Rica International Sports) all gained notoriety.
By the end of the decade, the tiny industry of a few operations had exploded into dozens of sites scattered across the Caribbean and beyond.
A new era of sports gambling had arrived: anyone with an internet connection (or a phone) could suddenly bet on games from the comfort of home, no trip to Vegas or shady bookie required.
Key Early Offshore Sportsbooks and Their Founders
Let’s take a closer look at a few pioneering offshore sportsbooks from the 1990s and the people behind them:
- Intertops (Founded 1983, online in 1996): Originally a phone-based bookmaker serving Germany, Intertops made history by accepting the first online sports bet in January 1996. It was founded by Detlef Train (a German bookie who moved to London in 1983 to start the company) and later spearheaded online betting under Simon Noble’s tech leadership. Intertops relocated part of its business to Antigua to remain accessible to U.S. bettors. This trailblazer showed that internet sports betting was feasible – and profitable – sparking a rush of competitors. (Intertops remains operational today under a new name, after decades in the business.)
- World Sports Exchange – WSEX (Founded 1996 in Antigua): WSEX was founded by Jay Cohen, Steve Schillinger, and Haden Ware, who were among the first to truly harness the internet for sports betting. Cohen (a former Wall Street trader) handled public relations and legal arguments, Schillinger and Ware ran the day-to-day operations. They obtained one of Antigua’s first online betting licenses and launched WSEX in late 1996. WSEX offered an innovative “sports trading” platform and grew rapidly through the late ’90s. However, its founders soon drew the ire of U.S. authorities (with Cohen eventually returning to the U.S. to face charges – more on that below). WSEX’s bold start paved the way for the many online sportsbooks that followed.
- BetCRIS (Founded late 1980s, Costa Rica): Short for Costa Rica International Sports, BetCRIS traces its roots to the phone operation of Ron Sacco in the Dominican Republic. After facing legal heat in the DR, Sacco and other American bookies migrated to Costa Rica in the early 1990s, where they found a hospitable environment for online and phone wagering. Under various names, the business evolved into BetCRIS/Bookmaker.eu – a highly respected sportsbook known for catering to professional bettors. Sacco, known as “Cigar”, became a legendary figure until his arrest in the early 2000s reminded everyone that U.S. law was still a threat . Nonetheless, BetCRIS’s model of an offshore call-center book with an online interface became the template for many others. Today, the company (now Bookmaker.eu) is one of the oldest surviving offshore sportsbooks.
- BetOnline (Launched 2001, Panama): BetOnline’s origins go back to a U.S. bookmaker nicknamed “Joe Junior” who was taking bets in upstate New York in the early 1990s. To escape repeated arrests, he moved the operation to Costa Rica around 2000, initially calling it BestLine Sports. By 2001, the site rebranded as BetOnline and later relocated its headquarters to Panama, which offered a friendly licensing regime for online sportsbooks. BetOnline’s growth accelerated in the mid-2000s, especially after it absorbed customers and staff from a rival (BetOnSports) that was shut down by the U.S. government. The driving forces behind BetOnline included Eddie Robbins III (its CEO) and a team of experienced bookmakers and marketers. Over the years, BetOnline built a reputation for reliability and became one of the major offshore books serving U.S. players. It stands as a prime example of how a small local bookie operation transformed into a global online sportsbook when given the right environment.
These examples are just a few of the early players.
Others like The Greek, Bodog, Sportingbet, 5Dimes, and Pinnacle also launched in the late ’90s or early 2000s and gained international followings.
But the companies above are often cited among the first wave that established the offshore betting industry.
Why Certain Tropical Havens Became Sportsbook Hubs
You might wonder, why did so many sportsbooks end up in places like Antigua, Costa Rica, Curaçao, or Panama?
The short answer: these jurisdictions made it easy – or at least possible – to run an online betting business, at a time when doing so in the U.S. was illegal. Each locale had its own advantages:
- Antigua: This small Caribbean nation was one of the first to explicitly license online gambling. By the mid-1990s, Antigua was charging a ~$25,000 annual fee for an interactive betting license (later raising it to $75k and $100k as demand grew). The Antiguan government welcomed offshore sportsbooks, seeing them as a source of jobs and revenue. Companies like WSEX and Intertops flocked here because they could operate legally under Antigua’s laws and serve U.S. customers via the internet. Antigua’s proactive approach even led to a WTO dispute with the U.S. in the early 2000s, as Antigua fought for its right to host online gambling that served Americans. Despite U.S. pushback, Antigua remained a key early hub.
- Costa Rica: Costa Rica became known as the “world capital of sports betting” by the early 2000s, hosting between 200 and 300 sportsbooks at its peak. Why Costa Rica? It had a perfect mix of factors: a stable economy, good telecommunications infrastructure, a large pool of English-speaking workers, and no specific laws banning online betting. In fact, Costa Rica didn’t even require formal gambling licenses for many years – sportsbooks could operate as regular businesses as long as they didn’t take bets from locals. The government largely took a hands-off approach (aside from eventually imposing modest licensing fees around the mid-2000s). This laissez-faire attitude, along with favorable things like readily available offshore banking in nearby countries (Curaçao, Dom. Rep., Antigua), made San José a magnet for American bookmakers in exile. By basing in Costa Rica, sportsbooks like BetCRIS, Bodog, and 5Dimes could run massive operations online and by phone, relatively free from legal interference. Costa Rica became the place to be for offshore betting companies – at least until U.S. pressure later in the 2000s made some consider relocating.
- Curaçao: Part of the Netherlands Antilles in the ’90s, Curaçao was one of the first jurisdictions to regulate online gambling, with a legal framework enacted in 1993 and licenses being issued by 1996. Its one-size-fits-all license was inexpensive and widely available, attracting numerous online casinos and sportsbooks. Curaçao gained a reputation for being a straightforward, low-tax licensing haven – basically a convenient flag of convenience for many offshore operators. While not as many sportsbooks set up physical offices there (compared to Costa Rica or Antigua), Curaçao often provided the legal license that legitimized an online sportsbook’s operations. Even today, a huge number of betting sites carry a Curaçao eGaming license due to its ease of obtaining.
- Panama: In the 2000s, Panama emerged as an up-and-coming hub for online sportsbooks. This financially stable, business-friendly country realized it could attract gambling companies leaving other jurisdictions. Panama City offered modern infrastructure and a highly developed banking sector (important for moving money), yet costs were lower than in Costa Rica. Panama’s government actively courted sportsbooks in the mid-2000s, even talking about bringing in a dozen major operators. They established a licensing system through the Panama Gaming Control Board, which BetOnline and others took advantage of. The only slight downside was Panama’s closer political ties to the U.S., which made some operators a bit nervous about potential cooperation with U.S. law enforcement. Even so, Panama became a significant base for some leading offshore books in the late 2000s and beyond.
In summary, these countries (along with others like Jamaica, Dominican Republic, Belize, and Isle of Man in Europe) provided a legal home for sportsbooks that wanted to take bets from the huge U.S. market (and other countries) where such betting was illegal or heavily restricted.
They offered licenses or safe harbor, decent tech infrastructure, and a pool of labor – all crucial ingredients for running an offshore sportsbook.
Without them, the offshore betting industry could never have gotten off the ground in the way it did.
Technology that Enabled Offshore Betting
Offshore sportsbooks owed their existence not just to legal loopholes, but also to technological advancements.
Two technologies in particular fueled the industry’s growth: telecommunications and the internet.
Telephone Betting: Before the web was widespread, offshore books relied on good old phone lines.
Using 1-800 (toll-free) numbers or international lines, bookmakers in the Caribbean could take calls from bettors in New York or California as easily as a local bookie could.
Thanks to fiber-optic cables and satellites, a customer could dial a number and reach a call center in Antigua or Costa Rica where English-speaking clerks would gladly take their bets.
This was a game-changer in the late ’80s and early ’90s.
A bettor could read the latest lines in a mailed newsletter or magazine ad, then call in to place a wager.
By the mid-90s, many offshore books had set up sophisticated phone banks; as one account from Costa Rica in 2005 described, a single sportsbook might have 200 phone clerks working busily on a football Sunday.
The ability to bet by phone from anywhere greatly expanded offshores’ reach.
It also helped that these books often advertised “no taxes” and better odds than Vegas, making that long-distance call quite tempting to serious bettors.
Internet and Online Wagering: Of course, the internet revolution in the mid-90s is what truly skyrocketed offshore betting.
Early on, just having a website was a novelty.
These sites were very basic – often just static pages with text, because 1994-1995 internet speeds were slow and browsers were primitive.
There weren’t even domain names at first (sites had awkward numerical addresses).
But as web technology improved, a few visionaries realized that bets could eventually be placed online, not just by phone.
Intertops’ team was the first to crack that code in 1996.
After that, companies raced to develop online wagering platforms.
By the late ’90s, many offshore books offered browser-based betting where a customer could log in, see live odds, and click to place bets.
It seems commonplace now, but at the time this was cutting-edge tech.
Implementing online betting had challenges: secure server infrastructure, software to track bets, and most critically, payment processing.
Early sportsbooks had to figure out how bettors would deposit money and withdraw winnings remotely.
They innovated by accepting credit card payments and bank wires, and later services like NETeller and Skrill arose to facilitate gambling transactions.
WSEX, for instance, proudly accepted credit cards and even did age verification checks online – steps that traditional street bookies never worried about.
This legitimacy helped gain customer trust.
Eventually, e-commerce improvements made it easy for a bettor to fund an account online, place bets instantly, and get paid out (in theory, at least) without ever speaking to a person.
Another tech element was live odds and results.
Sportsbooks invested in computer systems to update odds in real-time and grade bets quickly after games ended.
By linking their odds screens to websites, they could display up-to-the-minute lines to anyone online – something Vegas odds boards couldn’t do outside the casino walls.
All of this technology – online bet trackers, live updating odds, digital accounting of customer balances – formed the backbone of the modern online sportsbook.
By the 2000s, some offshore books even started offering live betting (wagering on games in progress) and mobile betting via early smartphones.
These innovations, developed out of necessity by offshore operators competing for customers, would later be adopted by the mainstream gambling industry.
In short, offshore books were the incubators for a lot of technology that’s now standard in legal sports betting apps.
U.S. Legal Battles and Enforcement Crackdowns
Offshore sportsbooks existed in a legal gray area.
From the perspective of U.S. law, these businesses were illegal – they were taking bets from Americans in violation of laws like the Wire Act of 1961, which forbids using wire communications (interpreted to include telephone and internet) to transmit sports bets.
But enforcement was tricky: if the betting took place entirely offshore, U.S. authorities initially struggled with jurisdiction.
As a Department of Justice spokesman admitted in 1998 regarding online betting, “If the casinos are outside the United States, there’s not a thing we can do about it except prevail upon the host government.”
For a few years, that meant a Wild West environment for offshore books – they operated openly and made a lot of money serving U.S. bettors.
It didn’t take long, however, for U.S. officials to start pushing back.
The major sports leagues, especially the NFL, were vehemently opposed to these offshore books (viewing them as threats to their games’ integrity and their own cut of gambling).
By the late 1990s, the NFL was lobbying the government to take action.
In 1998, federal prosecutors in New York unveiled indictments against 21 individuals involved in offshore sportsbooks, including WSEX’s founders Jay Cohen, Schillinger, and Ware.
Cohen, believing he was on solid legal ground in Antigua, flew back to the U.S. to fight the charges – and to the surprise of some, he lost, becoming the first person convicted for running an offshore sportsbook.
He was sentenced to about 18 months in prison in 2000, sending a clear warning to others. (Schillinger and Ware remained in Antigua as fugitives; Schillinger died there in 2013, and Ware lived many years in exile.)
This case showed that the U.S. could reach offshore operators, at least those who set foot on U.S. soil or had assets in America.
Another high-profile takedown was BetOnSports, one of the largest offshore sportsbooks of the early 2000s.
In 2006, U.S. authorities indicted BetOnSports executives and successfully shut down the company.
Its CEO was arrested during a layover in Texas, and the founder pleaded guilty to racketeering charges.
The U.S. also went after media outlets that ran offshore sportsbook ads, and payment processors that facilitated bets.
That same year, Congress passed the Unlawful Internet Gambling Enforcement Act (UIGEA) of 2006, which specifically targeted the money flow to offshore betting sites.
UIGEA made it illegal for banks and payment processors to knowingly process transactions related to online gambling (including sports betting).
This law didn’t criminalize placing the bets, but by choking off credit card payments and other funding methods, it aimed to starve offshore books of U.S. business.
The UIGEA had an immediate chilling effect on the industry: several publicly traded online gambling companies (mostly based in the UK) pulled out of the U.S. market overnight to avoid legal trouble.
However, many of the privately-run offshore books (the ones we’ve been discussing) continued on, using alternative payment methods (third-party processors, cryptocurrency like Bitcoin, etc.) to get around the banking blockade.
In the years following UIGEA, the U.S. Department of Justice continued to sporadically crack down on offshore operators.
Another wave came in 2011–2012 when indictments targeted sites like Bodog and even some popular online poker rooms.
Essentially, the message from U.S. authorities was: if you take bets from Americans, you’re not safe from our reach.
Yet, despite the risks, the demand from American bettors kept the offshore industry alive.
Until very recently, if you were an American who wanted to bet on sports, you only had a few options: fly to Nevada, use a local illegal bookie, or patronize an offshore sportsbook.
It’s estimated that billions of dollars flowed to offshore betting sites every year throughout the 2000s and 2010s, even as the U.S. DOJ tried to stop it.
Offshores adapted by becoming more discreet (no more flamboyant TV interviews like Sacco’s or bold U.S. ad campaigns), but they never went away.
Indeed, many continued to thrive by offering things U.S. bettors couldn’t get locally: credit accounts, extensive betting options, and anonymity.
Ironically, the persistence of offshore sportsbooks and the huge American appetite for sports betting eventually helped lead to a reversal in U.S. law.
States saw how much money was leaving the country via offshore sites and local bookies, and many grew eager to legalize and regulate betting themselves to keep that revenue.
This culminated in the Supreme Court’s 2018 decision to strike down PASPA, lifting the federal ban on sports wagering.
Since that ruling, over 30 states have legalized sports betting in some form, creating a booming new legal market in the U.S.
The NFL and other leagues have even partnered with betting companies – a far cry from the 1990s stance.
Legacy of the Early Offshore Sportsbooks
The early offshore sportsbooks of the 1980s and 1990s fundamentally shaped today’s sports betting landscape.
These pioneers demonstrated the immense demand for convenient, remote sports wagering – a demand that Las Vegas alone couldn’t satisfy under restrictive laws.
By serving U.S. bettors when nobody else would, offshore books kept the sports betting culture alive and growing.
They essentially proved the market’s size: even with legal risks and zero advertising on mainstream TV, millions of Americans were willing to wager online if given the opportunity.
This underground popularity laid the groundwork for the eventual legalization push; lawmakers couldn’t ignore that sports betting had gone mainstream.
Technologically, offshore books were the innovators of online betting.
They built the first platforms to accept sports wagers on the internet, developed online payment solutions, and honed the user experience of betting from a home computer or mobile device.
Features we take for granted now – like live odds updates, easy parlay bet builders, and mobile betting apps – have roots in the tools created by those early offshore operators competing for customers.
Even concepts like in-play betting and diverse prop bets were field-tested by offshore sites long before they were offered in Las Vegas.
When you open a modern sportsbook app from DraftKings or FanDuel, you’re using an interface and system that evolved from what those offshore pioneers started decades ago.
The offshore era also created a generation of expert bookmakers and bettors.
Many staff from early offshore books have since moved into the legal gaming industry, bringing their know-how to regulated sportsbooks. (For example, some U.S. companies quietly hire consultants who cut their teeth in Costa Rica or Antigua in the ’90s.)
The knowledge of setting sharp lines for a global audience, managing risk on huge volumes of bets, and balancing a sportsbook’s finances through wild swings – all that institutional experience largely comes from the offshore world.
It’s often said that offshore books “kept the fire burning” for sports betting during the dark years when it was outlawed in most of the U.S.
They created a huge base of seasoned bettors who were ready and waiting when legal alternatives finally arrived.
Of course, the legacy isn’t all rosy.
The offshore model also highlighted risks that modern regulators aim to avoid: players occasionally got burned when a shady sportsbook disappeared with their funds, and the lack of oversight meant no guaranteed consumer protections.
These cautionary tales influenced how states now structure legal betting (with strict licensing and bankroll requirements to protect customers).
And not all pioneers survived to see the new era – some, like Jay Cohen and Ron Sacco, paid a personal price in legal battles, and a few early companies collapsed under pressure or mismanagement.
Nonetheless, the influence of those first offshore sportsbooks is undeniable.
They paved the way for online sports betting to become a legitimate, multi-billion-dollar industry.
What started as a few guys taking bets from Caribbean phone banks has turned into a global enterprise where anyone in New Jersey or Colorado can legally wager on an app that looks a lot like the ones developed in Costa Rica years ago.
The story has come full circle: the same professional leagues that once helped shut down offshore books now embrace betting partnerships, and U.S. gamblers have options galore that were only a dream in the 90s.
We have the ingenuity and daring of the offshore sportsbook pioneers to thank for that evolution.
In the end, the question “Who started the first offshore sportsbooks?” can be answered by naming individuals like Gary Bowman, Ron Sacco, Jay Cohen, and others – but it’s also a story of why they started them.
They saw an opportunity to serve sports fans who simply wanted to bet on games, legally if possible, and they seized it.
They combined old-school bookmaking know-how with new technology and favorable foreign jurisdictions to build something groundbreaking.
The first offshore sportsbooks were started by risk-takers and visionaries operating on the fringe – and their legacy is a sports betting landscape that’s more accessible and innovative than ever, whether offshore or onshore.
