Today in MMA History: A boxing champ in tax trouble takes on an MMA star – sound familiar?

(Editor’s note: This story originally published on Aug. 28, 2017.)

On Aug. 26, 2017, UFC lightweight champion Conor McGregor earned the biggest payday of his career when he crossed over to unfamiliar territory, challenging Floyd Mayweather in a boxing mega fight worth hundreds of millions of dollars.

It was a bold move to go from one sport to the other, jumping in at the highest level with little opportunity to prepare and no relevant professional experience.

Seven years ago today, another fighter tried the same thing in the other direction. He did it for a fraction of the price, and put up nowhere near as much of a fight, even if he was just as enthusiastic as McGregor about the opportunity itself.

In late 2009 and early 2010, James Toney was a man on a mission. A boxing champion in three divisions, the 41-year-old Toney had begun showing up at UFC press conferences, where he was impossible to ignore as he insisted that UFC President Dana White give him an MMA fight.

“I want him to put his money where his mouth is,” Toney said after UFC 108 in January 2010. “Who’s better: MMA or boxing?”

It was exactly the kind of challenge that White was uniquely incapable of resisting. A longtime boxing fan, White reiterated his respect for Toney and his career accomplishments again and again. He’d been a champion as a light heavyweight, a cruiserweight, and a heavyweight by that point. He had more than 80 professional fights to his credit, and had been in the ring with legends of the sport like Evander Holyfield and Roy Jones Jr.

“(Toney) is actually a guy whom I respect,” White said. “This guy is tough as nails. He’s mean. He’s nasty.”

What Toney wanted most of all, it seemed, was a paycheck. Though he was technically a heavyweight champion after a controversial split-decision win over Fres Oquendo in 2008, Toney complained that no other heavyweight champs would fight him. In the boxing world, he’d begun to look like damaged goods. His age was showing. His speech sounded more and more slurred. He still had the same old stubborn arrogance and gleaming diamond jewelry, but he’d become more of a relic than a star.

To make matters worse, Toney was in trouble with the IRS, which had already seized a six-figure payday from him in 1997, and he needed a big fight to lift him out of the hole he’d dug for himself.

That’s where the UFC came in. While he might have lost a lot of his shine in the boxing world, in MMA was a novelty. He followed the UFC from Memphis to Las Vegas, using his mouth to make himself the center of attention as he demanded a chance to prove boxing’s supremacy. His true motives for doing this were not lost on White.

“How much is (Toney) making right now?” White said. “He’s chasing me around for a reason. He’s not chasing me around because he’s making money, you know what I mean?”

But the more Toney talked, the more MMA fans listened. There was something charismatic about him, in a slightly absurd way. Despite spending his entire life as a boxer, he claimed he had a well-rounded martial arts skill set that no one knew about. In a closed-door meeting with White, who peppered Toney with questions about leg kicks, Toney insisted on his abilities with a cool confidence that bordered on delusion.

“I know how to do all of that,” Toney said. “Front kick, back kick, all of that. Side check kick.”

He was apparently convincing enough for White. The UFC announced Toney’s signing on March 3, but said no opponent or date had been finalized for his MMA debut. Later that same day, former UFC light heavyweight and heavyweight champion Randy Couture took to Twitter with a suggestion.

I hope I’m the first guy they call to fight tony ! 🙂

— Randy Couture (@Randy_Couture) March 4, 2010

At first it seemed like a casual mention, but Couture refused to let it go. In subsequent interviews that spring he continued to express his desire to be Toney’s first opponent, presenting himself as the ideal representative for MMA’s battle for bragging rights.

“There’s been several boxers that have stepped up and run their mouths about mixed martial artists and how bad our striking is and how they’d knock us out,” Couture said that April. “That’s kind of created this rivalry, plus we’re always compared to boxing since I started this sport. So to have one of (boxing’s) former world champions step up to foray into mixed martial arts, I think it’s a big fight. It’s a huge fight. It answers some questions that people want to see the answers to, so I’m more than willing to step up and see that happen.”

That June, the fight was made official for UFC 118 in Boston. While it still seemed like a mismatch in terms of MMA experience, Couture was some five years older than Toney, making it seem like a bout between peers in at least one sense.

As the fight neared, Toney continued to perpetuate the ruse that he was secretly skilled in all facets of MMA. He was said to be working with Juanito Ibarra, who had trained Quinton “Rampage” Jackson for years. Other reports had him under the tutelage of jiu-jitsu ace Dean Lister. A rumor even spread that he’d even submitted former Strikeforce champion Mo Lawal with a guillotine in training.

For his part, Couture seemed unconcerned. Three weeks before the bout he threw out the first pitch at an Oakland A’s game to help promote UFC 117 that same day. Asked if he believed reports that Toney had been hard at work studying the ground game, Couture smiled and shook his head.

“Nah, I don’t believe that,” Couture said. “He’s probably doing some wrestling with Mo Lawal. That wouldn’t surprise me. I know he’s not training with Dean Lister. Dean called me himself when that one broke and said, ‘I’m not training with that guy. Don’t believe that stuff.’ But it doesn’t matter. All the talk is just talk. No matter who he can get to say he’s tapped them out in training, on the day he’s still going to walk down to the cage and get in there with me and that’s when all that stuff stops.”

As the fight got closer, Toney’s trash talk only intensified. MMA fans thought Couture was so great? He was going to teach them otherwise, he said.

“Ya’ll say Randy Couture does ‘dirty boxing,’ whatever the (expletive) that means, and he’s a wrestler. Hey, this is war for me – this guy, who ya’ll claim is the greatest MMA fighter to put gloves on. (Boxers) are the superior strikers. … I look at this as a way to let everybody know that boxing reigns supreme.”

At the same time, even Toney seemed to acknowledge that he was getting a skilled and experienced opponent for his MMA debut, and he knew what that meant. He was being “set up to fail,” he said, and seasoned observers had to admit there was some sense in his argument.

After all, while Toney brought a different kind of interest and maybe some fresh fans to the pay-per-view, there wasn’t much upside to the UFC in seeing him win. He was too old to have much of a future in MMA, after all, and he was adamant about continuing to box. To some, this seemed like a repeat of when the UFC signed Sean Gannon, the Boston cop who’d gained notoriety for an underground brawl with Kevin “Kimbo Slice” Ferguson, only to overmatch him in his first fight to prove a not-so subtle point.

But if Toney was worried, you couldn’t tell from his pre-fight remarks.

“If Randy Couture takes me to the ground, I will knock him out,” he said. “Ya’ll ain’t never seen nobody get knocked out from the floor, right? Ribs will be broken. I’m very comfortable from the floor.”

They were slated for the co-main event that night in Boston. A lightweight title rematch between champion Frankie Edgar and challenger B.J. Penn served as the night’s headliner. Toney paced in his corner during pre-fight introductions, sporting a physique that could best be described as unimpressive.

Couture, even at 47, looked chiseled from stone. As announcer Bruce Buffer reeled off his stats, Couture smiled sheepishly at the cheers of the fans, as if in anticipation of the treat he was about to offer the MMA faithful.

It didn’t take long for that treat to materialize. Couture stayed far outside of Toney’s range for the first 10 seconds of the bout, then shot in for a low single-leg that easily tripped Toney to the mat. Couture moved immediately to full mount, facing zero resistance in the process. With only 20 seconds gone in the first round, Toney was already in deep trouble.

“Who does not love Randy Couture?” UFC announcer Mike Goldberg said on the broadcast.

Couture peppered Toney with short punches from mount, while Toney did his best to hold on and hide his head in close against Couture’s torso.

“James is not hip-escaping,” said Joe Rogan, Goldberg’s partner on the pay-per-view broadcast. “He’s not putting his hands on Randy’s hips to push off. Randy’s got grapevines in here, separating the legs of James. He’s just beating him up here.”

Couture postured up and rained punches down as Toney tried to sit up. The Boston crowd launched into a chant: “UFC! UFC!”

Goldberg, apparently in an effort to make sure there was no illusion of impartiality, responded, “I love this.”

As Couture trapped a bloodied Toney against the fence, he slowly slipped on an arm-triangle choke and tried to finish it from mount. Toney made no attempt at a defense, but Couture paused the choke to alert referee Mario Yamasaki to what he seemed to think was a verbal submission.

“He said he gives,” Couture could be heard saying on the broadcast.

But Toney remained silent and impassive, neither fighting back or offering signs of surrender. It was if he thought the key to getting back to his feet was to remain as still as possible, hoping Couture might lose interest, like a cat with its prey.

Instead, Couture maneuvered him to the mat and slapped on the same choke again, this time moving to side control to finish it. Toney tried to follow his corner’s instructions by pushing down on his own hand to fight the choke, but it was no use. With a little over three minutes gone in the first round, Toney signaled his submission to Yamasaki and the fight was over.

“What we learned at UFC 1 still is applied at UFC 118,” said Rogan.

In his post-fight interview, Couture would explain that he opted to use the low single-leg mostly because of how seldom it was employed in MMA. It seemed like the takedown that Toney would be least prepared for, yet most vulnerable to. For the questionable achievement of submitting the boxer after two attempts at the same choke, Couture received his black belt from jiu-jitsu coach Neil Melanson.

But once his triumph was sealed, Couture did his best to offer an olive branch to the boxing community as he gave Toney his due for coming to MMA.

“I’m a huge fan of boxing,” Couture said in the cage after the fight. “A lot of credit to James for stepping up in here as the first boxer to do that. I think all us MMA guys love boxing, and hopefully now there’s a whole bunch of boxers like James that will start to love MMA.”

That was perhaps a tad too ambitious of a hope. Boxing sites described Toney as “helpless” and “defenseless” in the bout. The main debate was as to whether he’d embarrassed the sport of boxing or merely himself.

To make matters worse, the IRS put a lien on Toney’s reported $500,000 payday from the UFC. He’d taken a one-sided beating, and now he might not even get paid.

But then, few people expected anything different from the fight itself. Why would they? Who in their right mind would think that you could just jump into a whole new sport like that, with only a matter of months to prepare, and compete at the highest level?

Not Couture, who was quick to shoot down any speculation that he might be willing to try his hand against Toney in a boxing ring next.

“I will respectfully decline such an offer,” Couture said. “That would be as silly as I think it is for James to step into mixed martial arts here. It would go probably the same way. James would knock me out in the first round.”

“Today in MMA History” is an MMAjunkie series created in association with MMA History Today, the social media outlet dedicated to reliving “a daily journey through our sport’s history.”