088: Hawaii Fivo (Jordan Robertson) - The Glasgow Gangster

088: Hawaii Fivo (Jordan Robertson) - The Glasgow Gangster

When you think of Scottish crime stories, images of gritty streets, gang culture, and prison life often come to mind. But behind every headline, there's a human story. Enter Jordan Robertson, also known as Hawaii Five — a nickname that hides a past marked by street fights, knife crime, and jail time.

On the Criminal Connection Podcast, Jordan opened up about his life growing up in Glasgow, navigating violence, prison sentences, and ultimately, transforming his life through music and creativity.

Growing Up in Glasgow: A Tough Start

Born in 1992, Jordan grew up in Cardonald, Glasgow — an area with its fair share of rough spots. After his parents split when he was just five, Jordan moved with his mother to the Moss Heights, notorious high-rise flats known for crime and gangs.

Despite his mother’s efforts to keep him indoors and out of trouble, Jordan always longed for freedom. A love for reading and PlayStation games couldn't stop the inevitable pull of the streets. As a teenager, the desire for social acceptance led him into local gang circles, a common story in Glasgow’s gang culture.

The Search for Respect: Knife Crime and Violence

Unlike many of his peers, Jordan wasn't naturally aggressive or a fighter. But carrying a knife gave him a false sense of power. In his words:

“When I had a knife on me, people would give me respect.”

This craving for respect in a world of violence led him down a dark path. At just 16, Jordan found himself embroiled in gang fights, carrying knives not necessarily with the intent to use them — but to gain that feared reputation.

But as Glasgow’s knife crime laws tightened, his decisions caught up with him. An arrest after a gang fight, when police witnessed him ditching a knife, led to his first stint behind bars. What followed was a cycle of arrests, breaches of bail, and a growing familiarity with the Scottish justice system.

Inside Scotland’s Most Violent Prison: HMP Polmont

Polmont Young Offenders Institution, infamous for housing Scotland’s most violent young inmates, became Jordan’s second home. Inside, violence was a way of life.

From sharing cells with unpredictable inmates to setting fire to mattresses and even pulling off pranks like the now-infamous “kettle incident” (you’ll have to listen to the podcast for the full story!), Jordan’s time inside was marked by both foolishness and raw survival instincts.

But even in this harsh environment, a realization was growing inside him.

The Night That Changed Everything: Stabbing Incident and Attempted Murder Charge

One fateful night, after a cocktail of drink, drugs, and a toxic relationship spat, Jordan’s life took a turn for the worse.

Fueled by anger and paranoia, a confrontation escalated into a violent stabbing — an event that left his victim in intensive care. Facing attempted murder charges, Jordan was remanded back to Polmont.

Though he initially clung to denial and tried to outsmart the police with a fabricated story, the evidence was undeniable. He eventually pled guilty to a reduced charge of serious assault to severe injury, permanent disfigurement, and to the danger of life, receiving a 4.5-year sentence.

Prison Transformation: The Gym, The Guitar, and the Turning Point

Life in prison is often a dead end, but for Jordan, it became a catalyst for change.

He threw himself into the prison gym, transforming his body and mind. Later, in the final months of his sentence, he picked up a guitar — a moment that would unknowingly shape his future.

Through music, Jordan discovered a creative outlet that gave him a new sense of identity. From casual strumming to writing his own songs, this newfound passion lit a spark in him.

Life After Prison: From Chaos to Creativity

After his release, Jordan struggled with the trappings of his old lifestyle. Nights of drug-fueled partying replaced his prison routine. But deep down, the pull of music — and the desire to escape his past — never left him.

It wasn’t until the COVID-19 lockdown that Jordan truly began to reinvent himself. Dusting off his guitar, he started sharing funny songs and sketches on Facebook and TikTok, quickly building a loyal online following.

His unique blend of humor, storytelling, and music struck a chord, turning his past mistakes into relatable, sometimes hilarious content.

Podcasting, Acting, and Finding His Voice

Jordan didn’t stop at music. He launched his own podcast, Premeditated Patter, diving into Scottish culture, prison stories, and social issues with a raw honesty that resonated with listeners.

His talent even caught the eye of filmmakers, leading to acting roles in independent films and a stint on Channel 4’s Banged Up — showcasing how far he’d come from his days in a prison cell.

From Knife Crime to New Beginnings: The Hawaii Five Legacy

Today, Jordan Robertson — aka Hawaii Five — stands as a testament to the idea that no matter how dark your past, there’s always a path forward. Whether it’s through music, creativity, or sharing raw stories, Jordan uses his platform to inspire others, especially young people caught in the web of gang culture and knife crime.

Conclusion: A Scottish Story of Redemption

Jordan’s story isn’t just about violence or prison life — it’s about resilience, reinvention, and the power of second chances.

From the streets of Glasgow to social media stardom, he’s proof that even the roughest roads can lead to meaningful destinations. His journey reminds us that creativity can transform pain into purpose — a powerful message in today’s world.

Stay tuned for his upcoming debut album and follow his journey on TikTok, Instagram, and his Premeditated Patter podcast.

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