Bad Boy is a documentary that takes an intriguing approach to crime, personality and reputation. At its heart is the 2026 Securitas heist, when just over £50 million was stolen from the Securitas depot robbery in Tonbridge. By far the UK's largest cash heist, in fact, it was so big that the criminal gang had to leave £154 million behind because they didn't have space. Not that you'll learn many details like that from this documentary.

The subject is really Jeremy Bailey, the ‘Bad Boy' of the title, whose trial for concealing criminal property after the heist resulted in no conviction during some costly proceedings. It's this part of Bailey's life that this documentary uses as an anchor for a study of the reputational issues that continue to dog this livewire subject.

Bad Boy doesn't offer up facts per se, although judicial rulings and the factual incidents play a major role. Instead, it provides several talking heads and a host of anecdotes, opinions and interpretations to build a picture of the Securitas heist and Bailey's decades of run-ins with the police. With Bailey himself—first introduced alongside his car number plates SET IIP and PAY UP—taking most of the screentime, he makes a fascinating and engaging subject as he, essentially, sets out his stall.

As Terry ‘Turbo' Stone, partial narrator, player in proceedings, and co-director says about Bailey's involvement in the heist, ‘We will let you decide.'

Bad Boy retraces Bailey's quite extraordinary life, from growing up in Basingstoke, and his early brushes with the law, to his life-changing move into MMA. MMA may form the common link between those seven convicted for the Securitas Heist, but Bad Boy soon moves on to Bailey's more recent life, as he provides the kids of his home town the opportunities he never had through his lavish gym (complete with octagonal cage) or living it up in Marbella (gleefully called the Costa del Crime), where he's built a considerable network.

Bailey and others provide some lengthy anecdotes, often skating around the legality and sometimes stopping themselves in their tracks before they cross the line (“I've got to say that for legal reasons”). A self-effacing and gnarly anecdote from his days bouncing at Brixton Academy is reeled off as simply as the story of how he went through one tournament with a dislocated knee.

However, it's Bailey's long war of words and more with the police that provides a particularly fascinating spine. At one point, one of the teens from Bailey's gym colourfully recounts a recent police run-in she witnessed. Dropped in throughout is footage recorded by Bailey during the making of the documentary that shows him being stopped by police on the side of the road.

Perhaps, the most insightful input, though, comes from Bailey's droll lawyer. He described Bailey as being dogged by MI6 and NCA (over the top to the point of preposterous), but also incapable of change (choosing his strong belief of what's right and wrong over any risk of further action from the police). Alongside Bailey's input, it's crucial for us to draw our own conclusions.

The Securitas heist doesn't really come into proceedings (no pun intended) until well past halfway. With a sizable amount of money still missing (£31 million), Bailey makes some knowledgeable and astute observations on what could have happened to that money. When it comes to the legal process and the intricacies of the Securitas heist, he certainly knows his stuff.

With an extraordinary approach to an extraordinary subject, this 70-minute documentary is more than a snapshot of Bailey's life, and more than an interesting diversion for fans of MMA and true crime. It's food for thought.