A former gangster, once branded one of the most feared men in New York, has lifted the lid on his life of crime, from committing his first killing aged just 14 to becoming a hitman and beating several attempted murder charges.
Henry Medina, now 67, was the leader of a brutal street gang in the 1970s and 80s, running drugs, dodging death and taking lives, including his first victim, a 15-year-old boy, when he was still a teenager himself.
After a brutal upbringing, Henry began slipping into gang life and made a bold move at age 13 to approach a feared local outfit, the Galaxy Gang, asking if he could set up a junior branch.
He became the leader of the now-defunct Young Galaxy Gang, and it wasn’t long before he was tested with real bloodshed.
‘A few weeks after we formed the gang, some people broke into our clubhouse, and they messed it up, and we were told that it was a gang called the Caribbean Kings,’ he says.
‘So when we found that out, I told my gang, we’re going up there. And I grabbed a big knife.
‘I didn’t have intentions of killing somebody at 14 – I really didn’t. That wasn’t my intention.
‘My intention was to grab the knife so that I could look like a tough guy because at that time, that’s what everybody thought of me.’
Henry Medina was one of the most feared gangsters in New York after first killing at 14
But later, Henry found out the Caribbean Kings had nothing to do with the destruction – it was set up by the older members of the Galaxy Gang who wanted their younger counterparts to prove themselves.
Henry bursts into tears as he adds: ‘I wound up taking the life of an innocent young man. He was an innocent young man, 15 years old, and I took his life.
‘And I believe that the reason I did it was because I was holding all that anger from what my father did.
‘That was the thing that exploded. The anger came out, and I did what I did.’
Although Henry was arrested and sent to a youth detention centre, police were forced to let him go as no one would talk. ‘Snitching’ meant death.
‘I was in a youth house for three weeks. Nobody wanted to testify because they knew if they did, this was going to get even worse.
‘That was the rule in the street. You don’t talk about anything you do with your gang. That’s how I got away with it.
‘I eventually told them I did so they could let my friends go, but they still had no evidence to charge me, so they dismissed the case.’
Henry, who was just a teenager at the time of the crime was not punished for the crime as there was no evidence and no one was willing to talk
That deadly code of silence allowed Henry to continue rising through the ranks of the underworld, and his crimes grew darker.
‘Do I have other secrets? Yes. But the statute of limitations does not run out on homicides, so I’m not going to sit here and write a book and tell on myself about who I did what to,’ he admits.
‘I became a hitman, and I kept coming in and out of jail. So I cannot speak about certain things because I got away with them.
‘There’re some of it I just have to hold it in and never speak on it because the time of limitation never goes away.
‘The only things I speak about are things that can’t hurt me. I had five counts of attempted homicide – I beat that case.
‘The last time I went to jail, I was caught with 800 bags of heroin.’
Henry was only arrested that day by pure chance – police happened to raid the flat just as he walked in with the drugs.
Throughout the 70s and 80s, Henry cheated death again and again. He lived life on the edge every single day.
Throughout the 70s and 80s, Henry was involved in shootouts, police chases, and several crimes
He remembers a time when he and his friends were caught in a sticky situation that ended up in a rooftop chase and an escape reminiscent of a Hollywood movie.
He recalls: ‘I had a friend called Johnny – we used to go rob cocaine drug dealers – the big-time drug dealers. Not the little ones you see in the streets.
‘I’m talking about the ones that came off the ships and aeroplanes with kilos. One of our rules was not to rob the same place twice.
‘We robbed this place and made away with around $80,000 worth of money, drugs and jewellery.’
But with Johnny desperate for more money, he enlisted Henry and another friend, Jay, to go loot the same place, breaking their own cardinal rule.
Henry says he knew he had to be there to protect Johnny, as Jay could not be trusted.
‘Jay is a straight killer. He will kill his own mother if he wants to’, Henry says.
But this time, the trio were not so lucky.
He was last locked up in prison for dealing drugs after a life of crime, including serving as a hitman
Henry explains: ‘Johnny had this lady by the neck and used her as a shield as we made our way into the apartment.
‘There was commotion, but we didn’t know that it had led people to call the cops.
‘Some kid came running out of a room with his hands around his waist. I didn’t know what he had there, so I shot at him and hit him twice.
‘We got some money and drugs, but as we were coming down the apartment, we saw two cops who told us to freeze.
‘Jay ran to the rooftop, and one of the cops chased after him. The other one stayed with me and kicked the gun out of my hands.
‘But what he didn’t know was that Johnny always kept two guns with him. We suddenly heard a gunshot sound on the roof.
‘When the policeman who was with us looked up at the roof, Johnny shot at him and we ran away in opposite directions.
His friend Jay was chased all across the roof of the building but miraculously escaped.
Henry, with a fellow inmate at the Lompoc Penitentiary in California
In another incident, Jay provoked an altercation with drug dealers, leading to catastrophic consequences.
‘These Cubans chased us into a room, and there was no means to escape. Although they knew me, but started shooting at us.
‘I pulled Jay on top of me because I thought if they were going to keep shooting, they might as well shoot him.
‘They finally told us to leave, but Jay was all bloodied and shot up. I put him in the back of a cab and took him to the hospital – he survived, man.
But unlike Henry, his two friends didn’t live long enough to tell the tales of their colourful past.
Not too long afterwards, Jay was killed when a man opened a machine gun on him while he was in the toilet.
Henry says: ‘Jay did so much dirt to people. You live by the gun, you die by the gun.
Johnny was also killed when a rival slit his throat. Henry emotionally says he was in prison at the time of Johnny’s murder, so he could not do anything to help him.
Henry lived a dangerous life where he was forced to constantly look over his shoulders for rivals
Henry also had his own encounters where he was targeted by people he had wronged, including a man who wanted revenge for getting robbed.
‘He saw me in an apartment and pulled out a gun and started shooting at me. Of course, I ran. I didn’t go back to the neighbourhood for a long time.
‘When I robbed him, I had a mask on, but he was still able to know who I was. That told me that somebody had ratted me out to him.’
‘I beat five counts of attempted murder,’ he says calmly.
His gang’s power was so entrenched that they even had an informant inside the NYPD – a federal agent who helped them outsmart authorities and taught them military-style tactics.
‘We called him Mandigo. He went rogue, and he hung out with us. So he taught us a lot of different tactics on how to approach people in the street and how to get inside apartments,’ Henry says.
‘And then he had practice – we would flip over cars like we’re running, and we would throw ourselves, flip over the car.
‘It was crazy. I don’t know what the f**k had us doing this type of stuff.’
Henry, back, centre, now says he suffers from severe PTSD after everything he has experienced
Mandigo was eventually killed. He was set up, shot in the neck and paraded around the neighbourhood for people to see he had been slaughtered.
Now in his late 60s, Henry lives with the scars of his past. He suffers from PTSD and says the trauma of his crimes still haunts him to this day.
Henry believes his shocking childhood growing up in the tough streets of New York’s Lower East Side is what plunged him into a life of chaos.
Henry grew up in a home plagued by domestic violence and fear.
‘My dad was a drinker, and he used to get violent when he was drunk’, he explains.
He would put his hands on my mum, and I was too young to do anything about it. When I got in the middle, he’d start whipping on me.
Eventually, his mother found the courage to leave – but the terror didn’t end there.
‘One day, my father showed up to kill all of us. He had a knife to my mum’s throat.
Henry says his life of crime and gang activity stemmed from his difficult childhood
‘I didn’t know what to do, so I jumped on my dad and began beating on him with my older brother.
‘I took the razor from him and I wanted to cut his throat. My mum stopped me. She yelled at me and stopped me.’
To ask for forgiveness for the crimes of his childhood, Henry went back to the place where he had killed the 15-year-old boy.
He emotionally says: ‘I lit a candle up exactly where I stuck a knife in him, and I wrote a letter explaining to him how sorry I am and asked him to forgive me.
But instead of running from his past, he’s trying to turn his story into a warning.
Henry tearfully says: ‘God has a reason for me to stay alive after everything I have done to people – there’s got to be a reason. I’m now trying to do the right thing.
He’s written a book and now speaks publicly about his violent past in the hope of steering young people away from gangs.
‘I’m regretful for everything I’ve done,’ he says. ‘I want to give back. I want to help.’
Henry says he wrote his book to warn young people about the dangers of gang life
After his last stint in prison, Henry worked with gang members to help turn their lives away from a life on the streets.
His work, recognised by several organisations, has earned him many accolades.
These days, he lives with his 90-year-old mother, who he takes care of full time.
He has also held on to his lifelong passion as a graffiti artist, which he says always helped him in his dark days.
He was one of the people who pioneered graffitiing in New York City and made it the phenomenon it is today.
Many of his iconic designs, featuring his name Henry 161, can still be seen on trains and subways.
Once a feared gangster who ruled the streets and dodged the law for decades, Henry Medina is now a man searching for redemption.
