Canadian Haralabos "bob" Voulgaris the master in poker

He is a vastly successful bettor, poker player, and analyst who has built his fortune in poker and sports betting - and is a household name thanks to his unconventional and data-driven approach to the latter.

Born to Greek immigrant parents in Canada, money-making acumen is in his blood. His father was a successful restauranteur and owned a real-estate business in Winnipeg. His enterprise and hard work meant his net worth crept into the millions. However, gambling was not a strength. Indeed, he credits his dad for teaching him some crucial life lessons - though not for the reasons one might think.

In an interview with Business Insider back in 2011, he said:

“I learned a lot from my father, but most of the stuff I learned was what didn't work. I learned that if you didn't have an edge on something, you weren't going to win.”

His father went broke twice through gambling on cards, sports, horses, and anything you punt on, which is why Voulgaris refers to him as an "unsuccessful gambler" in an interview with the Guardian.

“They had to sell the house, the business. At 15, 16 I had to get a job to pay my parents' rent. That taught me that I'm careful about always being honest. I became untrusting. I'm grateful because it made me very self-reliant, resilient.”

After finishing high school, Bob had a gap year - travelling to Greece back to his cultural roots - before attending the University of Manitoba, where he studied philosophy. During this time, he started experimenting with data analysis and creating models to predict outcomes in sports games. And in 1999, he made the bet that changed everything.

Voulgaris was not naive to his father's problems—at 18, he often accompanied him on trips to Las Vegas. During his time in Sin City, Voulgaris spent much of his time watching and studying Basketball in sportsbooks. He was too young to be on the casino floor - the legal age requirement is 21 in the USA - but could try his hand at the NBA.

In 1999, he made the bet that would change everything and "fast-forward my life five years."

After looking at the odds for the Lakers to win the Championship—they were 6.5 when he placed the bet—Voulgaris compared the price to his model, which had them at a much shorter price, and decided to risk everything. He placed his entire life savings, approximately $80,000, on them to get the job done. They obliged, and his bankroll ballooned to half a million dollars.

His big sports betting win gave him the freedom to pursue another passion - poker, expressly limit hold 'em and cash games. He quickly became known for his ability to read his opponents and make strategic decisions based on their playing style.

Voulgaris has over $3 million in tournament winnings from a career spanning 14 years. His major hauls include sizeable cashes in the High Roller for One Drop and a memorable second-placed finish in the WPT Main Event No Limit Hold'em Championship 2005.

By 2018, the rise and rise of Voulgaris was the stuff of legend, and his light burned too brightly for Dallas Mavericks owner and eccentric businessman Mark Cuban to ignore. Cuban was, and remains, a big proponent of analytics and forward-thinking data collection - and Voulgaris ticked all the boxes.

He was brought in as a Director Of Quantitative Research. His remit was to develop strategies for data analysis, assess players, and provide in-depth reports to senior management after every game.

Sadly, it didn't work out. After his contract expired in 2021, the new president and general manager, Nico Harrison, did not renew it.

His sports franchise odyssey was far from finished—in July 2022; he purchased the Spanish third-tier club with the goal of bringing them back to the big leagues for the first time in more than 30 years.

CD Castellón is based in Castellón de la Plana, which is located on the east coast of Spain. The club was founded in 1922 and has since established itself as one of the most traditional and beloved clubs in the Valencian Community.

They have a passionate fanbase, as Voulgaris acknowledged when announcing the takeover back in July 2022:

“This team has the potential to be a LaLiga team. It has the local support from its fans, it has a very deep and rich history.”

Two years in and the project appears to be on track - at the time of writing, CD Castellón are top of the league with 60 points from 26 games. With 55 goals in that run, they are averaging nearly two goals a game. They are nine points ahead of Malaga CF, a team that was playing in the Champions League as recently as 2013.

Will Voulgaris' moneyballi-fication of Spanish football pay dividends? You wouldn't bet against it.