Life Mistakes: Paying to fight Kimbo Slice.

Kimbo Slice. Even the name sounds frightening. He’s huge, jacked, and angry looking. He’s got a penchant for wearing the Bahama’s flag out to the ring and shaving his chest hair in interesting patterns. His beard swallows souls (get close enough and you can hear faint whispers coming from it’s center). I could see why people might want to fight him in the MMA world; I understand that. He’s a marquee name and locking yourself in a cage with him (even if you lose) will probably land you attention and quite a bit of money.

But paying to fight Kimbo? Thats madness, and not British humor ape-in-a-library-messing-up-the-card-catalog madness, but the Leonidas-kicks-you-into-a-hole madness. And yet, there are several men out there who can make that very claim. During his street fighting days, before you were allowed to fight Kimbo, you had to put up 10 grand. That’s the deal. Your 10g’s v.s Kimbo and his crew’s. I wonder if these guys ever stopped to think why Kimbo’s crew was so willing to put 10 large up. Or if they’d ever seen a picture of Kimbo. Or if they’d ever looked in a mirror and really just, head-on-hands reflected on the direction their life was headed.

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Regardless, here’s a list of the guys who decided it was a good investment (Tip: it’s not).

Big D

Strengths: Not really knowing what was about to happen to him.

Weaknesses: Eye prone to explosion when bludgeoned.

This fight brought Kimbo to a new level of Internet fame. A backyard brawl where the combatants must consider, not just head movement and slipping punches, but also not destroying/impaling themselves on the home owner’s satellite dish (backyard brawl may disrupt service). Ends with Kimbo taking a punch on purpose directly to his face and then crushing Big D’s eye socket/orbital bone. Then they hug and someone talks about South beat records like anyone gives a shit about that. Big D’s new nickname is ‘Squishy Eye,’ one he doesn’t like but can’t seem to shake. (YouTube)

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Dread (Or Rasta)

Strengths : Bright enough to be afraid.

Weaknesses: Everything else, including hair.

We go from the backyard to the boatyard, where Kimbo damn near punches this ‘Dread’ character’s head straight off his shoulders. In retrospect, Dread probably should have invested in a industrial strength hair-tie, because 30 seconds into this fight it goes from interesting haircut to interesting way to completely blind yourself. Kimbo’s crew gives Dread a bottled water after the fight. Probably the most expensive bottled water he’ll ever drink. (YouTube)

Sean ‘The Cannon’ Gannon

Strengths: Ground fighting, actual training, submission acumen.

Weaknesses: Many but they don’t really come into play here.

Kimbo loses this fight, supposedly. Though it’s impossible to tell, as a good portion of the fight is really a shouting match/debate between the two crews on what the actual rules are. Someone should’ve typed those up (or at least written them down on a napkin) with $20,000 at stake. Between attempting a standing guillotine and being the first and only street fighter in a Kimbo video to throw knees from the clinch, Gannon was by far the most diverse fighter that Slice had faced up until this point.’The Cannon’ got a UFC fight from this where he was completely destroyed by Heavyweight guppy Brandon Lee Hinkle. (YouTube)


Strengths: Afro

Weaknesses: Afro

At the start of this video, we’re told that Afropuff (no, it’s not a snack food) weighs 300lbs. That’s a full 40 pounds on the 260 Kimbo Slice. Unfortunately, no one told Afropuff that being 300lbs and fat isn’t the same/better than being 260 with abs. Kimbo punches Afro so hard at one point that he makes a pigeon-esqe cooing noise, eventually succumbing after getting hit in the face a lot. Still has good hair though. (YouTube)

Big Mac

Strengths: Face constructed completely out of top-secret-government-project alloy, lack of concern for braincells.

Weaknesses: Fighting style resembles ancient ‘slap-fu’ AKA ‘the windmill.’

Big Mac is tough. That’s for sure. Unfortunately, his tactic of letting Kimbo hit him in the head over and over in hopes that he might faint/spontaneously explode into a ball of flame and beard particles ends poorly for Mac. Kimbo’s crew almost displays compassion by begging Mac to give up, as he is without his own corner man (boatyard man) to throw in the towel, or in this case, box of towels. This video holds the record for most knockouts in a single fight with the same 2 people fighting at five. (YouTube)


Strengths: Can crack his knuckles in a bizarre way.

Weaknesses: Jaw shatters when struck. Suffers from imaginary lats syndrome.

I can see why Adryan would take this fight. Suffering from ILS (imaginary lats syndrome) makes Adryan think he is much bigger/muscular then he actually is. Unfortunately, his imaginary lats can’t save his real jaw from getting exploded mere seconds into the fight. Listen to the interesting gurgle he makes after the first few punches.

Interesting tidbit, in this version that I linked, you see the cheapshot Kimbo takes when Adryan turns away. In other versions this is edited out. Hmmmmmmm. (YouTube)


Strengths: Apparent punching power, sporty headband.

Weaknesses: Dread strength, rule reading ability, cluttered garage causes panic.

This one’s exciting. Bouncer (probably a bouncer) actually hits Kimbo, or pushes him, and knocks him to the ground. He then proceeds to break the ‘rules’ of this bare knuckle street fight by hitting Kimbo while he’s down. This causes Kimbo to shoot for a double leg and charge Bouncer directly into a messy garage. I think I see a sweet neon green hat…and a bucket…some paints, and I think thats a door completely off hinges. The mess causes Bouncer to panic and run for his life, allowing Kimbo to land a bunch of unanswered shots, the end result being Bouncer slipping into the sweet hug of unconsciousness. There’s another round, which is basically forced on the poor guy because of the hit to a grounded opponent, but it only lasts a few seconds. Lesson is, don’t cheat in a bare knuckle contest with Kimbo or they’ll make you fight him even longer. (YouTube)


Strengths: Boxing, Chin, looks like some wrestling probably too.

Weaknesses: Agreeing to a stand up only bare knuckle fight with Kimbo, about 20 pounds.

The best actual fight of the bunch, it seems like poor Chico does has a good amount of actual skill. He shows some good head movement, footwork, hand speed and decent power, dropping Kimbo early in the fight. Eventually, Kimbo figures him out and cuts off the ring…errr…yard, trapping Chico in a corner. He beats him senseless. Chico gets back up (10g’s makes you do things) and gets hit again. He succumbs. They hug. Chico has blood on his face, but at least he’s got both his eyes. Kimbo looks in the camera and insists it “don’t stop.” His beard forces me to believe him. (YouTube)

Regardless of why they did it, respect to anyone who dares fight Kimbo in the street or the ring. I’m anxious to see him fight a ranked heavyweight, or at least someone I’ve heard of who isn’t famous for losing in exciting fashion (James Thompson). A bout against EliteXC heavyweight Brett Rogers should prove a good test.

4 thoughts on “Life Mistakes: Paying to fight Kimbo Slice.”

  1. Michael Terry

    Why on earth would you claim there was doubt about him losing to Sean Gannon? I've seen that video and he lost clearly.

  2. have to agree with Michael Terry. Gannon whooped his ass and the beating would have been much worse if not for his sham crew butting in.
    He's good at knocking out punks, but a trained fighter will whoop him up pretty good. That's whay he's only been fighting guys WELL on the wrong side of 40.
    Also the bouncer knocks him on his ass and his crew intercedes again claiming some sort of 'rules' violation. Who knew that existed in a STREET FIGHT. 🙂 Also, look at how many times Kimbo knocks people out by punching them in the back of the head (including the bouncer) That doesn't seem to be in the spirit of things.

    Also his original internet crew were a bunch of porno producers and he used to appear in a non-performer with girls role in many of them. They just reeked of a set up.

  3. A.D. - Columbia Coll

    If the rules where indeed 'no submissions' as many people claim, that minute long guillotine is a direct break of those. He loses, though, certainly.

    Good thing Gannon was smart enough to bring a bunch of his own people.

  4. What a ^%$&$%$ man!!!!!!!!!!!!!!!The magazine SEEKING GOSSIP reported him joined the rich men for beautiful women site"S e e k i n g R i c h . c o m " and he is mentioned to find his sugar girl there! the magazine foolx he????????????or fools us。。。。

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