The first undercover case that Kevin O’Leary ever worked on is a hard one to forget: a wife was looking to hire a contract killer to get rid of her husband. O’Leary’s team were responsible for going undercover, posing as the potential killer-for-hire, to find out if she was really serious and had murderous intent, was just indulging a fantasy, or perhaps it was a cry for help. Either way, they were going into a murky underworld looking for evidence to build a case. 

“Just a normal day at the office,” jokes the 61-year-old, who retired from the Metropolitan Police a decade ago after 30 years of active service, half of which was as the Head of Undercover Operations at Scotland Yard from 2002-2010. In a role that spanned everything from infiltrating organised criminal gangs to protecting the London Olympics – which he writes about in a new book, out this month – his phone didn’t stop ringing for years.

Back to the potentially deadly wife: how does one go about finding a contract killer? Is there a Yellow Pages advertising such services? How much do you pay? “There are networks of people who ask people – if you wanted one tomorrow, you’d contact the dodgiest person you know, they wouldn’t know but they’d ask along and chain until you get there,” he explains. (In the end, the wife backed out and the case was handed to another department).

O’Leary trained as a police officer at Hendon in the 1980s, having moved from Birmingham. He climbed the career ladder, leading investigations and running undercover ops where he sent officers into covert situations. He was also a negotiator in cases of kidnapping for ransom. “The hostage-takers would demand that the person was not to call the police, so my job was to go to work alongside them in secret, feeding them lines until we located the hostage.” 

Later his name was thrown into the ring for the most senior undercover role (although he doesn’t think he was meant to be the final candidate). “There was someone else they had in mind, but they kept failing the exam. I knew they didn’t really want me – and I’ve never stayed at a party where I wasn’t welcome – but it was a once-in-a-lifetime opportunity, so I went for it,” he says.

Going into covert ops doesn’t require any specific qualifications, says O’Leary, but the selection process, including psychometric tests, is rigorous. The training has a 30-40 per cent fail rate. “It is quite hard to get into undercover,” he says – and it is seen as an exciting role, but these days officer churn is higher than it once was because of longer service and reduced pension benefits.

Once in the role, O’Leary quickly realised the magnitude of what he was responsible for. “I was reading cases that had been in the headlines – unsolved murders, criminal groups so well-established that the seniors think they’re untouchable. My jaw dropped,” he says.

The process for deciding whether to go undercover, he says, involves asking: Have other tactics been tried and failed? Is there backing? Are we capable of sustaining this? Do we have the team? (Sometimes they borrowed officers from other countries around the world to make it work.)

One of his longest-running ops was known as Operation Peyzac in 2008-09. There had been a spate of teenage killings in Edmonton, north London, and the police had reached a dead end. “The public weren’t giving us anything, nobody saw anything, nobody heard anything. They were frightened. There was a wall of silence.” Even the confidential hotline was quiet.

O’Leary’s unit had to work out how to get into a tight-knit community without raising suspicion. “To parachute in would be the wrong question – you have to attract these people to you.”

The police decided to set up a music shop, BoomBox, fitted out with a recording studio that locals could use for £10 a session – and unknowingly, record their conversations. “As we’re setting it up, we add a whiff of criminality, we tell people ‘we’ll buy and sell stuff just don’t tell us where it is from’,” he says. “We tell kids they can use the studio for free if they don’t misbehave or bring the police to our door. Meanwhile all the [staff] are undercover officers.” 

To be convincing, the staff were trained in the sort of music the shop was selling (O’Leary says they trained officers to do anything from fly a plane to pole dancing if it was needed for a cover story.) The staff began to ask around to buy guns – getting them off the street and into the hands of law enforcement. “We bought 35-40 guns that year. At the start these were serious weapons but we knew we’d exhausted the supply when we started being sold air pistols,” says O’Leary.

In the end it was shut down with a big arrest phase – “you go in with the riot gear – a lot of people were sent to prison”. (Later, the Operation Peyzac defendants went to the Court of Appeal and argued they had been entrapped, but the judge ultimately found the police did not overstep.) 

By this point in his career, O’Leary wasn’t on the ground during these operations, but in the background making sure it ran smoothly, ‘running a plot’ as it is known: moving the pieces on the chess board, normally dozens of concurrent operations – several hundred in a year – keeping officers safe, or as safe as is possible while infiltrating organised crime. 

Did it ever go wrong? Did officers get found out? “Sometimes they do get confronted and beaten up – that happened a few times. But we’ve got a well-worn protocol to sort it out.” Not exactly “secret squirrel”, but it involves using a cover officer – someone who isn’t visibly on the ground but is a handler that bridges the undercover person and the police – and a metaphorical emergency button to notify them that they’ve been compromised. “My phone was on 24/7 even if I was on annual leave,” he says. (When he left the role, he called Vodafone to check his mobile was still connected as he was so shocked by the drop-off in contact.) 

One of the more common threats was the danger the officer posed to themselves in living a double life. O’Leary says there is a “corrosive” effect. “Imagine you’re deep infiltrating criminals and then have to go home, mow the lawn, and take the kids to park, as your true self. Switching out is really difficult,” he says. “That impacts them greatly the longer it goes on.”

Prior to O’Leary’s leadership, officers could remain full-time undercover indefinitely, but he changed that and required them to have an exit plan. “One of the biggest things a leader has to do in undercover is fight your own staff, because they’re so passionate and committed they don’t realise they’re burning out. [Because] they’ll be the first one to tell me I’ve broken them, that your family has split up, and you’re drinking too much because we left you in too long.”

Undercover policing has come under scrutiny in recent years, specifically with regards to ‘honeytrap’ relationships. Mark Kennedy, a Met undercover officer, posed as environmental campaigner ‘Mark Stone’ and formed close relationships with a number of women. O’Leary knew him personally. “Those undercover relationships were totally inappropriate,” he says, adding that Kennedy’s case was the perfect example of how corrosive long-term placements can be.

O’Leary is keen to draw a distinction between the work he did and that sort of undercover work. “Our objective was always to send cases to court for prosecution, so [everything we were doing] was always going to be looked at by a judge,” he says, whereas other units were “intelligence-gathering for internal consumption to build a picture” – for example, to understand what an activist group might be planning to do. 

“I’m not condemning [these] operations, they had their purpose, but what the police should caution against is mission creep – it gets wider and wider. It takes a really disciplined senior officer to call it and say stop, and I don’t think that was always done,” he says.

There are laws about what undercover officers are allowed to do and not do: they are governed by the Regulation of Investigatory Powers Act 2000 (RIPA) and the Home Office Code of Practice on Covert Human Intelligence Sources (CHIS). In 2015, former Home Secretary Theresa May set up the Undercover Policing Inquiry to investigate allegations, which is still ongoing.

But perhaps undercover work is always going to be controversial: a new BBC podcast featured undercover officer Neil Woods, who admitted: “I would seek out the most vulnerable people in those communities… [they] are the easiest to manipulate. If that sounds ruthless, well, of course it’s ruthless. A key thing about undercover policing is that it necessitates ruthlessness.”

The Met also continues to battle corruption and malpractice – seen most recently in the cases of Wayne Couzens, David Carrick, and the Charing Cross WhatsApp groups. “There was behaviour of some cops that was just deplorable,” says O’Leary. He saw firsthand corrupt officers uncovered during the course of his operations. “You can’t pick and choose what you discover when undercover. We’d be trying to investigate criminals and would be just getting a foothold and realise there were some officers on the periphery that are corrupt.” 

He still thinks of himself as police – referring to ‘we’. “I still love the organisation I spent 30 years of my life in, but I felt the rot start to set in about 2010. “It started changing, austerity came in and suddenly kicked out people who had a load of experience.” He says that to be a good undercover officer, at their core, one must have curiosity, be proactive, stay calm under pressure and manage yourself. “Everyone feels they are a Netflix detective these days.”

After decades in the force, even in his final role, O’Leary could hardly be accused of kicking back. He was appointed Commander for Crime and Intelligence for the London 2012 Olympics.

The security plans drawn up were extensive: missile launchers on tower blocks, a battleship stationed in the Thames (“it was a scarecrow – if you’re coming at us, we’ll fire back”) and also a wealth of less visible policing – combating fraud during stadium construction or environmental crimes from waste dumping, as well as increased rates of domestic violence, which happens alongside sporting events, regardless of medals or not. “We prepared for everything,” he says.

And was it alright on the opening night? “We had a protest group of cyclists – who’d been given approval to protest south of the Thames – but they came towards the Olympic stadium, they were just 100 metres away from the Queen’s convoy. Fortunately an astute copper saw a chance to direct them up onto the Bow flyover so they were elevated in the air when she came past. It was a stressful night, but we got away with it” [182 cyclists were arrested]. 

Looking at the force now, 10 years after he hung up his badge, does he think there are lessons to be learned? “Policies and processes might change, and there are different priorities, but human beings are the same, criminals are the same, and young enthusiastic cops are the same – they want to go in and change the world just like I did.”