Matthew ‘Moneyball’ Benham: Biggest Bets, Wins and Losses

Matthew Moneyball BenhamHaving started life in the banking sector, Matthew ‘Moneyball’ Benham was always a numbers guy, but after 12 years at Bank of America – and working as the Vice President no less – he made a huge change.

He went to work for Tony Bloom, another person on this list, at his newly founded company, Premier Bet. This was back in 2001, before the online betting industry had really begun, and Benham was responsible for creating predictive gambling models using quantitative analysis and analytical data.

They were seriously ahead of their time in terms of the depth of their research, and caught the online gambling wave at the very beginning too.

The business was successful but the partnership didn’t last long, because if rumours are to be believed, Benham and Bloom (which sounds like a florists…) had a falling out, and Benham left in 2003 to set up his own company.

That company was Smart Odds, opening in 2004, which provided betting information and analysis to punters and companies alike.

He didn’t just work in the betting industry though, Benham was a big gambler himself. He regularly placed big bets via betting exchanges, but in 2011 he took things one step further and actually bought an exchange of his own – Matchbook.

There have been murmurings that he only did this in order to get bigger bets on for himself, but the truth of this will likely never be known.

In fact, Benham is so secretive that not a single one of his bets is public knowledge. We know he bets big and often, but the specific details are a mystery.

The guy is supposedly worth around £300 million though, so you can assume his wagers are regularly in 6 if not 7 figure territory. He also loaned Brentford FC £700,000 in 2007, which is some indication of his wealth at the time, and which also began his journey as a football club owner.

Buying Brentford FC

Matthew Benham Brentford Promotion

From Brentford FC

Benham got his nickname, ‘Moneyball’, because of his approach after taking over Brentford FC in 2012. His analytical and data lead decision making process reminded many people of Brad Pitt’s character, Billy Beane, in the movie Moneyball. It came out in 2011 so was fresh in people’s minds around the time Benham bought the Bees.

It wasn’t the only club he bought though, also purchasing the Dutch side, FC Midtjylland, in 2014. He did this specifically to test his analytical modelling methods, before taking what worked and applying that to Brentford, which was his boyhood club and main focus. In essence, he used FC Midtjylland as his guinea pig.

It worked too.

He sold FC Midtjylland in 2023 to a Danish billionaire, and no doubt at a profit too considering they won the Danish Superliga 3 times and the Danish Cup twice during his tenure.

He’s still in charge at Brentford though, who were promoted from League 1 of the EFL the season after he took the reigns, then promoted from the Championship to the Premier League seven seasons later.

What’s more, in their first Premier League season they finished 13th, and the next season they finished 9th. For context, most newly promoted teams struggle not to relegated again right away, so Brentford really made an impact.

His insistence on following data and statistical probabilities also led to a much stronger financial situation for his club, enabling them to buy young players with great promise on the cheap, and make a huge return on them when sold on years later.