Posted 12/01/2014 by Jesse Scheckner in Island Fights

MMA/Boxing Hybrid Event Island Fights 31 Just the Next Big Step for Dean Toole’s Island Fights

Square Ring Promotions owner and boxing legend Roy Jones Jr. and Island Fights Championships founder, CEO and matchmaker Dean Toole's big plans for 2015 will start early this Friday with their inaugural MMA/boxing hybrid show. | Photo: Facebook

Square Ring Promotions owner and boxing legend Roy Jones Jr. and Island Fights Championships founder, CEO and matchmaker Dean Toole’s big plans for 2015 will start early this Friday. | Photo: Facebook

Hybrid Theory

If you live in Florida, its surrounding states, or are familiar with the name Roy Jones Jr., chances are you’ve heard of Island Fights Championships. Based out of Pensacola, the Florida-grown organization has been putting on some of the most consistently exciting fights in the southeast region of the United States. Founded by CEO and matchmaker Dean O. Toole, the promotion will be putting on its 31st show in four years this Friday, December 5.

This time there will be a twist; Island Fights 31 marks the first time that both mixed martial arts and boxing will grace the card.

An MMA/boxing hybrid event was always something Toole and Jones, whose Square Ring Promotions splits the profits down the middle with Island Fights, were interested in doing. However, permit troubles—specifically the Florida Boxing Commission’s previously immovable stance on MMA and boxing being unrelated sports requiring two separate $1,800 permits—proved to be too hefty a price tag. Furthermore, Toole argues, the two sports, although technically different, were similar enough that being charged twice was unnecessary.

Fortunately, the FBC’s new executive director Paul Waters is of the same mindset.

“This is something we’ve wanted to do the whole time since we started this, to do boxing and MMA on the same card, because no one else is doing it,” Toole explains.  “When Paul came into office and got the new job, we met with him and I asked him—I said, ‘Hey, we really want to do these shows. We’re one of the only people besides Fight Time and RFC who are continuously doing professional shows in Florida, we want to keep doing them and this is something we really want to do.’ And he said, ‘You know what, call me on Tuesday and we’ll see what we can work out. It makes sense. It’s one event; there should only be one permit fee.’ So he agreed with us, let us do it and now we’re going to be doing it on every show. It’s just something no one else is doing.”

Something else very few promotions in South Florida are doing that Island Fights is—something that makes them uniquely suited for holding these types of hybrid shows—is holding these fights, both MMA and boxing, in a boxing ring.

“We use a ring—I’m a big Pride fan; I loved it when Affliction came out and I thought their ring was awesome—and this is mixed martial arts. Everyone brands it as ‘cage fighting,’ but it’s mixed martial arts. That’s what we want to do. We’ve got tons of boxers on the gulf coast no one’s even seen yet and if you see these guys fight you wouldn’t even believe it. It’s amazing.”

Flexibility between the two pugilistic sports and an affinity for Japan’s most famous promotion aren’t the only reasons Island Fights chose forego following the UFC’s lead in terms of setting. Holding fights in a ring, Toole says, just plain looks better live.

“Look at a UFC event. Dana White’s s looking at TV screen, Joe Rogan’s looking at a TV screen and they’re sitting right at the cage. I go to fights in Biloxi, they have the screens on the wall and the whole entire crowd—they’re 10 feet away from the cage—the whole crowd has their necks titled to the wall to watch the video. On TV, the cage looks amazing when you’re sitting there watching it on the couch, but if you’re going to a live event and want to watch live, fights there’s nothing better than a ring.”


Dean Toole grew up a military kid, coming by his affinity for combat sports honestly and his father Robert, a standout All-Conference wrestler from Florida, saw fit to educate his boys therein. While stationed in Scotland, the elder Toole competed in and won first place at the Commonwealth Games and wrestled for the Scottish national team. Unfortunately, a bad weight cut ended his quest for Olympic gold, forcing him onto an alternates list from which his name was never called.

The Toole family returned stateside to Chicago and Dean and his brother Ryan—“the standout wrestler of the two of us”—continued the family tradition until Dean and Ryan’s 10th grade and senior year, when a move back to Florida and into a school with no supporting program put a premature end to their wresting aspirations. When Ryan graduated, he once again followed his father’s footsteps and joined the military and was stationed in Hawaii. His natural inclination towards grappling arts made him a perfect fit for the MMA upswing occurring on the island and he soon was rolling at Relson Gracie’s gym, training at 808 Fight Factory, trading punches with Chris Leben and competing in jiu-jitsu competitions including Naga, Grapplers Quest and Grapple Fest.

Dean looked up to his brother, as younger siblings do, and was inspired by his resurged enthusiasm. When Ryan moved back to Pensacola, the two of them went into business together. What started off as a modest retail enterprise selling MMA-related apparel eventually turned into the burgeoning promotion it is today.

“We had a little kiosk on the military base and we used to make a killing selling Tapout, Throwdown, Hitman Fight Gear… just all of those brands back in the day when people wore fight shirts. I moved to a store in the mall, but soon Tapout was selling their shirts through Champs Sporting Goods and Pacific Sunwear, and every single store in the mall now had all these brand and I kind of had to close that deal. When I had the store, everyone wanted to train. My brother was back from Hawaii, everyone wanted a place to train and [the sport] wasn’t that big back then. We opened a gym—a huge facility—and had world champion boxing coaches at the gym, Ezra Seller. Derrick “Smoke” Gainer used to train at our gym. We had a state championship wrestling coach—Keith Erickson from Virginia. We had Rico Holanda as our Brazilian jiu-jitsu coach. He was a purple belt at the time. I had that open for about four years. [MMA} wasn’t legal in Florida, so we do these amateur kickboxing and boxing shows and then, when it became legal, we started doing our shows, but the fights go so busy that I couldn’t keep the gym open. When you’re in the fight business you can’t do anything else. So that’s kind of how it took off. My first-ever fight was on Pensacola beach, and it’s an island, so that’s why we call it Island Fights.”

(L-R) Square Ring Promotions' McGee Wright, undefeated Island Fights heavyweight star Dillon Clecker and Island Fights CEO Dean Toole. | Photo: Facebook

(L-R) Square Ring Promotions' McGee Wright, undefeated Island Fights heavyweight star Dillon Clecker and Island Fights CEO Dean Toole. | Photo: Facebook

Tilting the scale

Looking over Island Fights’ history, specifically its many events’ fight results, one thing sticks out more than anything else: there are a hell of a lot of finishes—a disproportionate amount compared to other similar promotions. The reason for this anomaly is simple enough; Island Fights is something of a specialty regarding one specific weight class: the heavyweights.

“Let me tell you how that panned out, because it’s really interesting. Dillon [Clecker, undefeated at 7-0 with seven finishes, who is headlining Island Fights 31] is one of my really good friends. I always make it a point when I find an opponent for him, that they know this. This isn’t an ‘I’m setting you up against Dillon Clecker to lose’ type of situation. After the last four years of trying to find someone to fight him, it’s the hardest thing in the world. The [fighters with] really good records won’t fight him because they have a goal to get into the UFC and if they take a loss they go ten steps backwards. You’ve got to be on a four or five fight win streak in this sport to get into the UFC or you have to be undefeated.”

Toole breaks off momentarily to explain that this isn’t really the case with Richard White, Clecker’s opponent this Friday, and although his record on sits at 18-16 (inaccurate, he says, asserting that White’s record is 25-16), White started off his career with eight or nine consecutive wins before running into some trouble once the level of his opposition rose.

“The reason I have so many heavyweights is because I’ve always had to search for heavyweights for Dillon. I’d go find all these heavyweights—I was constantly out talking to and recruiting heavyweights—and I started to develop relationships with so many of them. Now they all call me and it’s kind of crazy situation. I literally have about 50-60 heavyweights. Our biggest problem, honestly, is that we don’t have enough room to put these guys on.”

Future growth

Moving forward, Toole has high aspirations for his and Jones’ business. They plan on remaining in Florida for the time being, expanding their reach to Orlando, farther south into Palm Beach County and doing four shows annually in both areas, bringing their yearly schedule up to 12 events. They’re also in the market for a TV deal and are still considering using Jones’ sizable presence not only promotionally, but possibly competitively as well.

“There are a few things we’re working on, but sometimes this business is about who contacts who. We’d like to do some stuff with Roy in the future, perhaps get him to fight on one of the cards. We’ve talked about that. That’s the overall plan. Roy’s been trying to do this Anderson Silva fight for a while, but [Silva] just extended his contract with the UFC, so I’m not so sure how that would play out. There’s talks about Rampage Jackson, if you’ve heard that recently and Kimbo Slice—those types of things.”

Now that South Florida MMA kingpin Championship Fighting Alliance is gone, Island Fights is positioning itself to fill the void Oscar de la Noval’s now-defunct promotion left behind, and Toole believes they’d be an ideal fit—especially considering their larger-than-usual roster.

“We’d love to be on TV. An AXS TV type deal… that would be perfect for us. These other people are getting these deals, but we’re that company. You’ve got all these camps in Florida, all these gyms down south, and when we go down south hopefully all those guys will be fighting on our shows. The only thing we’re missing is a TV deal.”

Island Fights Championships 31 is taking place on Friday, December 5, 2014 at the Hadji Shriner Temple in Pensacola, located at 800 W. Nine Mile Road. Doors open at 7 p.m. For more information, visit the Island Fights website and follow them on Twitter, Instagram and Facebook.


A freelance MMA, entertainment and business journo born, raised and residing in Miami, FL, Jesse Scheckner is a musician, cinephile and recovering ne’er-do-well who still believes Mickey Rourke’s finest days in film have yet to come. He‘s editor-in-chief. Follow him on Twitter: @JesseScheckner.

Jesse Scheckner

A freelance MMA, entertainment and business journo born, raised and residing in Miami, FL, Jesse Scheckner is a former semi-serious musician, cinephile and recovering ne’er-do-well committed to nonfiction storytelling. He is the 2014 Florida MMA Awards "Best MMA Media Correspondent" winner and a two-time Miami New Times "Best Of" winner. Follow him on Twitter @JesseScheckner to talk about the stuff he writes about with him.