A young football star who ended up on the wrong side of the law has opened up about the sickening moment he came face-to-face with a depraved serial killer as part of a daring, top secret undercover mission that saved countless lives.
James “Jimmy” Keene’s incredible life story is portrayed in the award-winning Apple TV+ true crime series Black Bird, featuring stars including Taron Edgerton, Greg Kinnear, Ray Liotta in one of his final roles, Paul Walter Hauser, who won the Golden Globe for Best Supporting Actor – Television Limited Series/Motion Picture for his performance in Black Bird.
Now, the former sports star-turned-prisoner-turned-hero is speaking out about the incredible experience that changed his life, telling news.com.au about the huge personal sacrifice that could have cost him his own life.
Keene had a tough upbringing in the south side of Chicago as the eldest of four children, with the young family forced to rely on his mother’s part-time waitressing salary following his parents’ divorce when he was 10 years old.
His father went on to remarry and start a second family, and money was tight for many years.
“We were dirt poor at that point, not to mention that I’m from the south side of Chicago, which had the highest crime rate in the nation through this era, and when I was growing up it had the highest unemployment rate in the state,” Keene told news.com.au of his early days.
“The options for any kind of success in that place were limited … So where did that lead me?
“We had nothing. I was a decent-looking guy, but that doesn’t really give me automatic privileges.”
Keene eventually got involved in the marijuana business, and by the time he was 17, he was making serious money, deciding to turn down scholarships to universities in other states and instead remain in the Chicago area to attend a junior college while still playing football and wrestling and continuing his business.
“It wasn’t even a conscious thought at that age – if I’m making half a million, a million a year, and eventually way more, why would I walk away from the business when I could just go to college here in Chicago and build up my savings?” he said.
“I went to college … and had a blast and the weed business grew and grew.”
Keene is adamant that he believes in individualism and allowing others to do as they please, although he personally never uses drugs.
“If a person wants to do something, then who am I to tell you no? But I was into my sports, with football, wrestling, martial arts, track and field and hockey keeping me busy all year, so I didn’t want to be smoking weed,” he explained.
Over the years, Keene’s weed business grew, and he eventually became minimally involved in “blow” (cocaine) too – as well as a string of other legal businesses, including a real estate firm, high-end car dealerships, a restaurant and Italian food company and a strip club.
The businesses grew from strength to strength, and he was able to buy a “mansion” at the age of 20 overlooking Lake Michigan, where he hosted epic parties attended by celebrities.
“I was a very entrepreneurial guy, a businessman by nature. I was making millions and millions as a 20-year-old,” he said.
But in the mid-1990s, when he was in his early 30s, things came crashing down when he was finally arrested on hearsay conspiracy charges as part of Operation Snowplow, a major police operation tackling drug offences which resulted in more than 170 arrests.
In the end, he was sentenced to 10 years in prison after two former lifelong friends turned on him, claiming he had sold them drugs – but failing to recall specifics such as quantities and when and where the alleged deals took place.
“The judge had to calm me down four times in my evidentiary trial … I was arguing, saying ‘she the hearsay witness is lying, she can’t remember a single thing – times, dates, places, so called amounts’. But I got railroaded anyway and shafted and sent to prison.
“But I still had four appeal options, and they knew I was probably going to get something reversed back on appeal, get some time knocked off my sentence. They knew I’d find a way to get out of there.”
Then, not too long into his sentence, Keene was approached by Assistant US Attorney Larry Beaumont, who had one hell of an offer for him.
Initially, Keene believed the authorities wanted him to snitch on local gangsters or cartel members – something he refused to ever do.
“I didn’t snitch on nobody, and I could have told on everybody and their brother and never spent a day in jail,” he said.
“I was never going to tell on someone – that’s not the cloth I’m cut from.
“All the mobsters in the Chicago area – the mafia was real, and they were very powerful people, and I was involved with them as a young guy. They loved me, they said ‘Jimmy man, you’re the most stand-up guy we’ve ever seen.”
But the offer being made to Keene was beyond anything he could have imagined – to become an undercover agent, transfer to the Springfield maximum-security prison and befriend notorious serial killer Larry Hall in order to extract a confession out of him – in exchange for having his sentence waived and his record scrubbed clean.
Initially, Keene wanted nothing to do with the bold plan, but was finally convinced after his beloved father had a stroke, and he realised he wanted to be able to spend as much time as possible with him.
“I broke down and cried – this man was superman to me for my whole life, I thought … I have to do something,” he said.
“Unlike [what was shown] in the Black Birdseries, there were no other candidates – Beaumont wanted only me. Beaumont came to me and wholeheartedly wanted me and only me to do this.”
At the time, Hall was preparing to appeal his sentence, and according to Keene, he would have won as there were a string of paperwork mistakes that likely would have seen his sentence overturned.
“There were plenty of technicality issues because the Feds were in such a rush to arrest him they messed up, and he definitely would have had his case overturned,” he said.
Keene recalls being shown a thick accordion file with photograph after photograph of dead and mutilated young girls – Hall’s victims – and being told he was the only one who could help keep the monster behind bars.
“I said, ‘I’m not a serial killer hunter, but how can I help?’” he said.
“Beaumont said ‘If he gets out, he’s going to kill again, and I’ve been watching you for 20 years – you’ve got charisma from the street level to the boardroom unlike anyone I’ve ever seen before, you’re trained in martial arts so you can protect yourself in a dangerous environment, you have an IQ of 168 so it’s hard for people to get something over you, and you’re trained in police counter surveillance. Hell, you’re an outlaw James Bond. You’re the only guy I can think that can do this and I know you can pull this off’.”
Keene said it wasn’t an option to send in undercover FBI agents as their true identities would be obvious within seconds in prison, although they attempted to train him in “FBI 101” in the lead up to his transfer to the new prison where he would come face-to-face with Hall.
However, while Keene wasn’t looking forward to “befriending” the cold-blooded killer, he was confident that if he could pull it off – it would be on his own terms.
“I definitely didn’t want to be in his presence because he repulsed me,” he said.
“But my biggest apprehension was that he was so cagey, so if I said one wrong little word, he would go into his turtle shell and he would never be coming out. My fear was that I had to be so smooth – if he didn’t want anything to do with me, then we were screwed and it would be all over.”
