What the Killer Did Next

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The strange tragedy of Helen Bailey

In Crime+Investigation's new true crime series What the Killer Did Next, Philip Glenister looks at how modern sleuthing techniques can piece together the exact movements of murderers in the hours and days after they commit their darkest acts.

One case explored in the series is that of the celebrated author Helen Bailey. It’s a saga riddled with eerie ironies and unlikely twists and turns, beginning with one shocking death – her husband’s – and ending with another, her own, at the hands of the man she regarded her 'happy ever after'.

When bad things happen in good bikinis

Before her life changed one tragic day in 2011, Helen Bailey had an enviable, happy life. She was the much-lauded creator of a series of teenage novels centred around her schoolgirl heroine, Electra Brown, and was happily married to businessman John Sinfield. They’d met while working at a company that handled licensing rights for iconic characters like Snoopy and The Simpsons. 

What the Killer did Next: trailer

Deciding they were both working far too hard, in early 2011 the happy couple jetted off for some much needed R&R in Barbados. It was here that on one sun-drenched morning, while Helen was relaxing in the rays, John decided to go for a swim in the seemingly calm waters. He was caught by a riptide and drowned right there and then (a horrible irony, given that Helen’s Electra Brown novels all had titles with swimming-related puns, including Out of My Depth and Swimming Against the Tide).

Watching it all unfold in front of her, Helen was struck by how perversely unreal it all seemed, thinking to herself 'But I’m wearing a bikini, but I’m wearing a bikini'. The rude intrusion of death in the middle of a perfect, serene Barbados day inspired her to write a book called When Bad Things Happen in Good Bikinis

It chronicled how she came to terms with this sudden loss, and her slow evolution from anguish to a semblance of normality, with the help of her beloved dog, Boris. The book also touched on a new relationship with a prince charming who heralded a new chapter in her life. This prince charming was Ian Stewart. Her future murderer.

The 'gorgeous grey haired widower'

Ian Stewart was a former software engineer who, like Helen, had suffered a terrible bereavement. His wife had collapsed and died, apparently, from natural causes, one year before Helen’s husband took his fateful dip in Barbados. In fact, Helen first started chatting to him on a social media site for widows and widowers, at which point he started bombarding her with messages of affection, in a targeted 'love bombing' campaign to win her attention.

Helen later wrote about how he wasn’t even her type, and it started off as the purely platonic sharing of private grief. But, despite Ian Stewart’s unprepossessing appearance on their first physical meeting ('he turned up in a battered red Ford Mondeo estate with a Micky Mouse car aerial topper'), she soon fell in love with the man she would fondly dub the 'GGHW', or Gorgeous Grey Haired Widower.

It wasn’t easy for Helen – she felt like she was betraying the memory of her husband. She was even attacked online by members of Planet Grief, the online community of bereaved people she’d created. 'Some widows were angry with me,' she recounted, 'disappointed that I'd gone back on my earlier conviction that I'd never fall in love again.'

But she became comfortable with her new life, and the promise of lasting happiness Ian Stewart brought her. Thanks to Helen’s wealth, they were able to move into a large, plush house, and made plans to get married. Yet things were amiss. Helen’s mother became concerned about her daughter’s state of mind. Helen complained to her of feeling spaced out all hours of the day, and falling asleep randomly. One day she wandered out of a supermarket while still holding an item scanner; another time, she left her precious dog Boris on the beach. 

It wasn’t long after this that Helen – who, in another dark irony, had always dreamt of working in forensics, saying 'I’m positive if they just let me near the crime scene dressed in a fetching white boiler suit and gloves, I’d soon work out whether it was Colonel Mustard with the dagger in the library, or Mrs Peacock with the rope in the ballroom' – went missing. Her dog, too.

It took months for the truth to emerge – the truth of Ian Stewart’s real motivations, how he’d played with Helen’s mind using drugs, and the cold, remorseless cunning he’d employed in betraying and murdering the woman who looked on him as a hero in her time of need.

Since his conviction, Ian Stewart has come under increased scrutiny regarding the death of his wife in 2010, with detectives saying that – in light of what happened to Helen – they were prepared to re-evaluate whether Stewart’s wife really had passed away from natural causes. Could there be even more revelations to come, in a story that already defies belief?