Our SiGMA series, “The Online Gambling Industry: Tales from the Past,” is changing things up this time with Ian Sherrington interviewing Bryan Bailey, the founder of Casinomeister – and it’s a wild ride.

Before ‘player protection’ was even a thing, Bryan Bailey was already holding operators to account. In 1998, he launched Casinomeister.com, a site that started as a personal project and turned into one of the most trusted names in online gambling. For 25 years, Bryan ran the show with a mix of sharp thinking, transparency, and zero tolerance for nonsense.

He wasn’t a gambler. He was a creative writing professor who got into web design and had a bad run-in with a casino client that didn’t pay its bills. That was the spark for Casinomeister: a platform built to highlight good operators, expose bad ones, and give players a place to be heard.

And heard they were. From the infamous Pitch a Bitch complaint system to the Evil Player of the Year awards, Casinomeister became the go-to hub for real talk, whether you were a player chasing your winnings or a casino wondering why you just got dumped into the Rogue Pit.

In this interview, Bryan looks back at the early tech days, the scams, the CEO email chains, and the player disputes that made headlines, including the $4.1m jackpot case that still boggles the mind. He also talks candidly about his decision to sell the site, his cancer diagnosis, and what’s next for the Casinomeister legacy.

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