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The popular sports and trading card-breaking web show hosted by rapper Conway The Machine and Ian Schwartzman premiered with Mike Tyson as the first guest.

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The former heavyweight champion joined a list of celebrities who appear on the show, talk about hip-hop, and more importantly, rip open packs of rare sports and trading cards. As they sat down for a chat, the opening episode of “Rippin’ 2gether,” Season 2, sparked a deeply emotional moment, particularly for Mike Tyson when Conway the Machine narrated his story about a harrowing shooting incident.

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“I got shot in the head and in the neck, and I thought I wouldn’t even be able to rap again in 2012, and I got a little dark in my mind and a [expletive] up headspace and all that [expletive] like not knowing if I wanted to do it anymore,” the rapper said.

He was talking about the life-threatening situation that developed after he was shot in the head and neck. As a result, Conway the Machine, whose real name is Demond Price, suffered paralysis on the right side of his face, commonly known as Bell’s Palsy.

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Left with a permanent speech impediment, the incident forced him to relearn normal activities like eating and talking.

However, the setback only stirred him to fight back and put his career back on track, leading to founding a new label called Griseida Records and Drumwork. During that period, one of the biggest inspirations came from Mike Tyson’s life.

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“I didn’t know if I wanted to keep going and stuff, and then I watched a guy like you, who, you know, respectfully, I’m sure you’ve been seeing both sides of the coin—the ups and the downs more than probably a lot of us,” the rapper added. “How do you navigate through that? Like how you push through it? What gave you the resilience, the motivation to be like, ‘Nah, f**k that. This ain’t the end for me?'”

In response, the former heavyweight champion revealed that his biggest motivation came from the realization that he needed to stay ahead of everyone else, rather than allow anyone to see him slide downhill.

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When Schwartzman pointed out how Tyson had been carrying that mindset and outlook in every endeavor he had ever undertaken, the boxing legend could barely hold his tears. “I’m the monster,” he said, before adding, “That’s my security.”

Sitting among the hosts, Tyson clearly felt embarrassed as he became emotional.

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Yet, his tears say a lot. While he may not have faced a scary situation like Conway the Machine did when someone shot at him, Tyson has also come through dangerous situations in life. Growing up in a dangerous neighborhood, the heavyweight champion faced uncertainty from an early age.

Compounded by a troubled family life, Tyson was often a victim of bullying that pitted him against much bigger guys.

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“I was abused any way a human being can be abused as a kid,” Tyson said in an interview with GQ. “So, I don’t know, I’ve been bullied all the time. It has a profound effect on me, being bullied. I wish it didn’t, but it had a real profound effect. I’m kind of… I’m a really sensitive guy, and I’m… How can I explain this? For being bullied, I could be really, really malevolent, you know?”

Following a life in crime, things didn’t change until he picked up boxing. Once he picked up the tools of the sport under Cus D’Amato’s care, Tyson became a changed person. From someone who was once afraid, he became one of the most feared fighters in the world.

Looking back, as Tyson himself described, he adopted that mentality to ward off rivals and naysayers. However, like Conway the Machine and many others, Tyson’s adversity ultimately helped shape him into a stronger person, allowing him to reach unprecedented heights.

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Jaideep R Unnithan

3,892 Articles

Jaideep R. Unnithan is a Senior Boxing Writer at EssentiallySports and one of the division’s most trusted voices. Since joining in October 2022, he has brought a deep love for the sport into every story, whether reporting on live bouts with the ES LiveEvent Desk or unpacking the legacy of fighters from different eras as part of the features desk. Trained under EssentiallySports’ prestigious Journalistic Excellence Program, which is a specialized training initiative designed to refine top writers' skills through mentorship and advanced sports journalism techniques, Jaideep’s writing reflects a quiet authority shaped by two years of covering boxing’s flashpoints and fault lines. He is drawn to the warrior code of legends like Alexis Argüello and Marvin Hagler, while also staying attuned to the promise of rising stars like Jesse 'Bam' Rodriguez, David Benavidez, and Dmitry Bivol. Jaideep has a special fascination with Naoya Inoue’s old-school grit. Beyond writing, he reads widely, a habit that sharpens his storytelling, whether he’s tracing the rhythm of a classic fight or preparing his next ringside dispatch. Before joining EssentiallySports, Jaideep worked as a client manager and team manager in corporate roles, bringing strong organizational and communication skills to his journalistic career. He has also completed notable certifications, including a Non-Fiction Book Writing Workshop.

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Yeswanth Praveen

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