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The massive, stoic Russian perched on a chaise lounge in blissful comfort on a gorgeous beach. It was July 2009, and Fedor Emelianenko, the baddest man on the planet, was on holiday.

He should have been in the final days of training for his heavyweight fight with Josh Barnett at Affliction: Trilogy in Anaheim, California, but that event, and Affliction Entertainment itself, had shut down in the wake of Barnett's positive test for a banned substance. Fedor had only learned of the cancellation when he arrived in California.

So he brought his family to a favorite destination, the island nation of Curacao, with its colorful buildings, majestic palm trees and gorgeous beaches. They relaxed in the dry, Caribbean heat—a welcome contrast to the bitter cold in Stary Oskol, Russia. Fedor swam, ate and played with his daughters away from the public eye and the mixed martial arts circus.

That is, until his family time was unceremoniously interrupted one afternoon by Zuffa and UFC owners Dana White and Lorenzo Fertitta, who had flown in to negotiate a potential deal with the Russian's management team.

At the time, the top heavyweight on the planet—his knockout win over Andrei Arlovski six months earlier had brought his win streak to 26—was managed by Vadim Finkelchtein, a tall Russian with businesses in St. Petersburg and the Netherlands, including an ownership stake in mixed martial arts organization M-1 Global, which he had founded in 1997. The Russian promotion's main financier, influential banker Sergey Matviyenko, was also present.

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With a net worth of several billion dollars between them, the parties collected near one of the island's many beaches to break bread. Not known for his patience and diplomacy, White made an offer to sign Fedor and threw in a deal to purchase M-1 Global, Finkelchtein told the Russian publication Prosport (h/t Bloody Elbow). The language barrier made matters more difficult as tension began to run high.

While the figure offered remains a mystery (rumored as high as $30 million and to include a blockbuster matchup against Brock Lesnar, per CBS Radio's Carmichael Dave), it was insulting enough to make Matviyenko—at that point resting silently on a lounge chair—jump to his feet and laugh.

Matviyenko—vice president of one of the largest banks in the Russian Federation and son of Valentina Matviyenko, one of the most powerful women in Russian politics—was clearly unimpressed with the offer. As M-1 Global's majority shareholder, Matviyenko's opinion was pivotal. The Russians had rejected the world's largest MMA promotion. It wasn't the first time, and it wouldn't be the last.

White has spoken harshly of Fedor, dismissed his talents, called his management liars. But for almost a decade, he's kept up the chase. Fedor Emelianenko, who once again will fight under a non-UFC banner when he meets Matt Mitrione at Bellator 172 on Saturday, is his white whale.

Only those who attended the famous "island meeting" can recall the series of events that unfolded on that summer's day in Curacao. Unfortunately, both sides have given vastly different accounts of the infamous encounter.

White's expletive-filled retelling (warning: NSFW language in link) to reporters involved Russians who thought they were "too cool, too slick and too f--king funny" to make a deal with the UFC. He claimed that he offered Fedor a matchup against Lesnar and the most lucrative contract in UFC history up to that point.

The UFC president told the media that at one point, he warned Fedor (warning: NSFW language in link) of a danger every fighter at a peak earning opportunity faces: "You're one punch away from being worth zero."

The Russians, however, remember matters differently. In the Prosport interview, Finkelchtein called the UFC's proposal that day a "normal" one, while Fedor told MMAFighting.com's Chuck Mindenhall the promotion never mentioned Lesnar until after the Russian retired in 2012. Fedor also stressed that it was White's brash attitude that helped stir the tension, while Finkelchtein maintained that the UFC had exaggerated M-1's demands and offered a contract that would have tied him exclusively to UFC.

There were many other opportunities to secure a deal with the Last Emperor, but that fateful day on the beach was as close as the two sides would ever come to getting together. Close to six years later, when Finkelchtein was asked whether he would have offered a different answer than Matviyenko had he owned M-1 at the time of the island encounter, he said, "I do not know, honestly. Maybe I would have sold," per Bloody Elbow.

Had things played out differently that day—had the difficult Matviyenko not been M-1 Global's majority stakeholder and commanding voice, or had billionaire egos not exacerbated tensions—the greatest heavyweight in mixed martial arts history could have showcased his unparalleled talents inside the UFC Octagon.

We are left instead with a tale of what could have been and why it never came to be.

Pride before the Fall

On the final evening of 2006, Fedor Emelianenko defended his Pride heavyweight title for the fourth and last time at the promotion's annual New Year's Eve event at the Saitama Super Arena in Japan.

He spent most of the bout trapped beneath challenger Mark Hunt, a heavyweight kickboxer from New Zealand with 50 pounds on Fedor but little grappling experience. In the ninth minute, the champion pounced and finished the fight with a slick kimura that yielded an instant tap.

Years later, Hunt recalled the fight in his autobiography, admitting that "If there was one dude who knew how to finish a submission, it was Fedor."

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Hunt's show of respect was typical of the public discourse around Fedor. At the time, he was considered the greatest heavyweight to grace the sport and potentially the best pound-for-pound talent in its short history.

His mystique was equal parts inexplicable athleticism and stoic personality that craved little attention but commanded the spotlight all the same. His modest Russian background and pious disposition perfectly contrasted with his violent profession—human traits in a superhuman character.

Pride's dissolution in 2007, coupled with an expired contract, meant that the Last Emperor was a free agent seemingly ripe for the UFC's picking. Having purchased its Japanese rival, the U.S. flagship organization made it seem inevitable that it would get the heavyweight champ to cross over. White explained to the media at UFC 76 that it would be "crazy for him to fight anywhere else other than the UFC."

Even most MMA fans believed it was simply a matter of when, not if, the top free agent on the market joined the UFC.

Instead, Fedor held a press conference in New York City on October 22, 2007, and announced he had signed with M-1 Global as the promotion's centerpiece.

M-1 Global had undergone significant changes. Finkelchtein, who'd founded the promotion in 1997 as Russia's first professional MMA show, sold his majority share to Sibling Sports, LLC. The new owners hired longtime MMA promoter Monte Cox as CEO. With an influx of money and an ambitious plan to produce regular international shows across Europe and the United States, the promotion looked to Fedor to be its ambassador.

Despite the unexpected signing, Fedor had the option to compete in various promotions, depending on whether they could meet his lofty contractual demands. According to MMAWeekly.com's Ken Pishna, M-1 Global explained that Fedor's contract has a "clause to offer the UFC champion $1 million over and above what the UFC would offer their champion to fight Fedor, and $1 million to the winner of that fight over the general purse for that fight."

At the time, this was far above what the UFC was interested in paying.

The press conference was also where the co-promotion negotiation tactic first surfaced in the Fedor saga.

"We really want to work with all of the other organizations," Cox said, per Pishna. Referring to UFC heavyweight champion Randy Couture's split with the company days earlier, he said, "If the UFC gets Randy back and they call and want Fedor to fight, we'll send him to the UFC."

Three days later, a frustrated Dana White appeared on a UFC conference call (h/t All Wrestling) with Lesnar, Chuck Liddell and Wanderlei Silva.

The media call was scheduled to discuss a renewed TV deal with Spike TV, Lesnar's anticipated UFC debut and the Liddell vs. Silva fight at UFC 79. However, one media member's mention of Fedor was enough to divert White's attention. Asked his opinion about Fedor's decision to sign with M-1 Global, the UFC's head honcho said, "Fedor sucks."

White went on to blame Fedor's management for the UFC's inability to sign the heavyweight. He referred to Finkelchtein as a "f--king liar" and said his management team is "full of s--t." Fuming, White closed out his rant with a definitive statement: "Fedor isn't even a top-five heavyweight, let alone top pound-for-pound. ... Good luck to him wherever he's fighting because I don't want him in UFC.

"Do I need to say anything else?"

Maybe not, but the UFC president would nonetheless spend the next few years chasing his white whale.

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On February 8, 2008, Fedor penned an open letter to White and the UFC, which was translated and posted on M-1 Global's sports website M1MixFight.com (h/t MMAJunkie). The letter slammed White's long list of disparaging remarks. Fedor wrote that "allowing yourself to say those things is not a sign of a gentleman or a grown man at all." He challenged White to make the Couture fight happen and insisted that he "won't tolerate" more insults from White.

But it was the concluding statement that ensured White and Co. wouldn't comply: "I'm signed with M-1 Global and this promotion is ready to organize such fights under our banner or in co-promoted events."

Co-promotion was something the UFC refused to consider and M-1 Global refused to advance without.

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While the UFC wouldn't comment on the stalemate to Bleacher Report, White likely didn't want to set a precedent that fighters and their management teams could share in the UFC's success. M-1 Global, however, had recently acquired new shareholders, and the executives had ambitious goals to achieve in a relatively short period of time. According to Finkelchtein, in order to ensure the promotion could produce events on an international scale despite a modest roster, M-1 needed to enter into agreements with other promotions for its fighters.

A co-promoted UFC event with Fedor as the headlining act would have likely reaped immense profits and helped grow M-1's brand. Given that mixed martial arts was still illegal in Russia, M-1 was forced to try to establish itself outside of its home base. It eventually did venture into the United States, though not as a partner of the UFC.

Fighting for Trump

On June 5, 2008, future President Donald Trump held a press conference at Trump Tower in New York to announce a new mixed martial arts venture, Affliction Entertainment. The organization planned to host pay-per-view events that featured a roster of UFC veterans, plus heavyweight king Fedor Emelianenko as its crown jewel.

In October, Affliction announced a planned 15-episode reality TV show titled Fighting Fedor that would follow the heavyweight in Russia as he prepared for an upcoming match.

"The show will be spectacular, unique, and is going to be a special event," Trump said in an Affliction press release. "It will be taped in St. Petersburg, Russia. I'm going to be there, but I don't want to compete on the show."

While Trump and Fedor began a working relationship long before the businessman's pivot to politics, the Affliction deal and proposed reality show were noted by the Hillary Clinton campaign as one of the key ties between Trump and the Russian Federation, particularly because of Fedor's loyalty to Russian President Vladimir Putin.

The Clinton campaign even referred to the former champion as "Putin's favorite mixed martial arts fighter." According to Finkelchtein, however, Fedor signed with Affliction not only because it offered him a more lucrative contract than the UFC had but also because it treated him with the respect he was due.

"It was all about business," Finkelchtein told Bleacher Report through translator Daria Litvinova. "No one knew he would become a president then. I remember him as a smart, successful businessman who understood what he needed to do very well. It was an M-1 and Affliction co-promotion, and he represented the Affliction side. We had a press conference and weigh-in in Trump Plaza, visited his office several times. He greeted us very kindly and with all respect. I saw he supported Fedor in his fights and respected him a lot as a sportsman."

The Affliction deal further soured the already rancorous relationship between Fedor and the UFC. Not only had Fedor thwarted the UFC's plans again, but he had partnered with Trump, whom the UFC considered a friend because he had allowed it to host two consecutive events at the Trump Taj Mahal casino in Atlantic City, New Jersey, when the promotion was at an all-time low in terms of popularity and legality.

After the second Affliction event in early 2009, a furious White proclaimed that "Affliction is going away. They did horrible, horrible buys on Saturday night," he told Steve Cofield of ESPN Radio 1100. White said he'd "love to see them do another show because I'd love to see them lose another $5-6 million of their T-shirt money."

He was right. While Affliction had ambitious plans to conquer the MMA space and compete against the UFC, the promotion had already put on its last show. When Barnett tested positive before his match with Fedor in July, Affliction cancelled its third event and announced it was folding.

The promotion's financial troubles were in part a result of the Russian heavyweight's compensation. Fedor's contract with M-1 Global paid him $300,000 per bout, plus a $1.2 million consulting fee, according to Politico's Michael Crowley, which helped guarantee that Affliction did not profit from its already high-budget shows.

Less than a month before the unceremonious death of Affliction Entertainment, Lesnar, the former WWE star, had headlined the landmark UFC 100 event in Las Vegas with a rematch against former champion Frank Mir.

While an online campaign to have fans chant "Fedor" at the show fizzled, White once again spoke of signing the elusive heavyweight.

"We'll end up getting that deal done," White said at the UFC 100 post-fight press conference. "And then we'll do Brock vs. Fedor, and it'll be a huge fight."

With Affliction's demise, Fedor was once again a free agent. The UFC appeared to be closer than ever to signing him. The Curacao meeting was just around the corner.

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By July 30, 2009, MMA's major websites were reporting Fedor Emelianenko had turned down an astonishingly lucrative three-fight UFC contract. According to MMA Fighting, FanHouse reported that the heavyweight's proposed purse was less than $2 million per fight and that he had been offered a title shot against champion Lesnar in his UFC debut.

The two sides sniped at each other. White called Vadim Finkelchtein "Vadummy" and called his demands, which White said included the UFC building M-1 an arena (warning: link includes NSFW language) in Russia, egregious. Finkelchtein denied asking for an arena and said, "I think if Fedor wanted to fight in the UFC, he would have already been there."

Finkelchtein said White and the UFC were not flexible. "They refused to give him the right to perform in combat sambo," he said, "and that was very important to him."

Instead Fedor signed with Showtime to compete for Strikeforce. According to sources close to Fedor at the time, the deal was not only richer than the UFC's latest offer, but it contained far fewer restrictions than the UFC had insisted on.

"That was a very interesting time, because I know both sides had a meeting and they chose to come fight for Strikeforce, not the UFC," Strikeforce founder Scott Coker told Bleacher Report. "Rumor has it that the offer that was made was quite sizable."

Coker had a cordial relationship with the Russians, which likely played a factor in Fedor's decision to eventually sign with Strikeforce. While Fedor's contract was still a multifight, multiyear deal, he was working with a promoter he trusted, which Coker believes was a pivotal factor.

"Back then, it wasn't really between Fedor and myself," Coker said. "There was a third party involved, which was M-1 Global, and anything that involved dealing with M-1 was very challenging. Trust was definitely a factor."

Fedor made his Strikeforce debut on November 22, 2009, against undefeated Brett Rogers. The heavyweight was coming off a KO victory over former UFC champion Andrei Arlovski and was widely considered a top-10 fighter at the time.

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Though the UFC attempted to counter the CBS broadcast by replaying the UFC 102 fight between Couture and Antonio Rodrigo Nogueira on Spike TV, Fedor's promotional debut was a success. Following a tense start that saw Rogers break Fedor's nose, Fedor floored his opponent with a thunderous overhand right to secure the final victory of his unparalleled win streak.

Eight months later, Fedor lost to UFC veteran Fabricio Werdum by triangle choke—an unceremonious end to one of the most memorable eras in MMA history.

Fighting in Putin's Russia

On November 20, 2011, Moscow's Olympic Arena packed in over 20,000 fans to witness Fedor's return to Russia. Though then on a three-fight losing streak—stoppage losses to Antonio Silva and Dan Henderson had followed the shocking submission by Werdum—Fedor's mystique lived on in his native land. He was a shadow of his former self, but that shadow still loomed over the sport he'd dominated for so long.

Broadcast cameras caught occasional glimpses of then-Russian Prime Minister and former President Putin with a slight smile on his stone-cold complexion. He was there to support the legendary Russian athlete as he fought former UFC title challenger Jeff Monson.

The crowd chanted Fedor's name as he peppered his American foe with typical accuracy, albeit diminished speed and power. He expanded his arsenal to include a few kicks, breaking Monson's leg—though Monson fought on, losing by decision.

"When the adrenaline wore off on the way back to the corner," Monson told Bleacher Report, "that was the last step I took for six weeks."

Monson's valiant performance earned him a private congratulatory call from Putin and made him one of the most popular American fighters in Russia, where he's since competed more than 30 times and is pursuing citizenship. But Putin's popularity was at an all-time low.

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After the decision was announced, Putin stepped into the ring to publicly congratulate Fedor on his performance and was booed by the crowd. "We have never seen anything like this on this scale before," Russian commentator Konstantin von Eggert said soon after, per Guy Faulconbridge of Reuters. "It is a symptom that some in Russian society are tired of Putin's image."

While that M-1 Global event was believed to have perfectly captured Russian society's views on Putin at the time, it was also a pivotal moment when Fedor took on a larger role in Russian government. His association with Putin would lead to the legalization of MMA in the Russian Federation in 2012, as well as Fedor himself becoming the president of the Russian MMA Union, the sport's regulatory body. In exchange for his newfound career in sports administration, Fedor would become a political tool in Putin's re-election campaign.

Fedor's transition from full-time professional fighter to sports ambassador had begun. And it would take place under Putin's watchful eye.

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Ahead of the 2012 election, Fedor—seen as a role model for his piety, modesty and success—campaigned for Putin, who won a third term for presidency with 63.6 percent of the vote. This form of sports diplomacy is common in Russian society, particularly among Olympians and famous athletes interested in a political career following retirement.

While Fedor was already a deputy of the Belgorod Regional Duma, representing the loyalist United Russia political party, his support for Putin eventually helped him replace Russian Prime Minister Dmitry Medvedev as a staff member of Russia's Council of Physical Fitness & Sports. The decree was signed by Putin on July 28, 2012.

Having cemented his post-MMA career, Fedor's chances of joining the UFC were minimal at best. Given his unparalleled stardom and ability to leverage large paydays in his own country, Fedor had little reason to court offers from the Las Vegas-based promotion.

He fought on two more occasions, against Satoshi Ishii in Japan and Pedro Rizzo in Russia, both of which ended in KO victories. Fedor shook hands with a casually dressed Putin, who made a second appearance at an M-1 show in June 2012 to offer the legendary heavyweight a proper send-off.

Yet while Fedor was settling into his cushy post-fighting career, the UFC tried its luck one last time.

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"We did," White said when asked if UFC gave Fedor a chance during a 2012 MetroPCS live chat. "We [recently] tried to get Fedor, and Fedor has absolutely, positively retired. He does not want to fight anymore."

Asked whether Fedor deserved the acclaim he received over the years, White finally relented: "Yeah, he's one of the greatest heavyweights ever."

A Legend Returns

"I feel that it is time to return to the ring."

Those were the words uttered by Fedor in a statement as he announced his shocking return to professional competition on July 14, 2015, more than three years after retiring. Within a matter of days, websites had already resurrected the longstanding stalemate between Fedor and the UFC.

Once again, it seemed likely that Fedor would sign with the world's top MMA organization. M-1 Global founder Vadim Finkelchtein confirmed that his partnership with the Last Emperor had ended upon his retirement. According to the promoter, Fedor was now managed by his wife, Oksana, as well as the Russian MMA Union.

For many, this signaled the much-needed breakthrough in the negotiation process—Finkelchtein's exit ensured that co-promotion was no longer a factor during negotiations.

In fact, Finkelchtein says he was responsible for renewed UFC talks in 2015.

"When Fedor came back, he asked me to help him go to the UFC," Finkelchtein told B/R. "So I entered into negotiations with them and they offered him really good conditions. I wanted him to fight in the UFC and I also realized that it was the only organization for him if you know his level, his skills, his big paydays, his popularity. And only UFC could offer him fights with athletes at his level."

The stage was set. The heavyweight even confirmed during a Q&A session that negotiations were in progress and that he wanted to face the "strongest fighters in the world."

Then came the plot twist.

Fedor shocked everyone by appearing on a Bellator broadcast and announcing a New Year's Eve matchup on the newly minted Rizin promotion in Japan. Given that Rizin was run by former Pride FC boss Nobuyuki Sakakibara, it looked like Fedor was more comfortable with the devil he knew.

"UFC made an offer, true," Finkelchtein said. "We had a conference call with them, and Fedor asked them to send the offer to him by mail. They did. After that, he went to the USA to a Bellator event where his deal with Rizin was announced. I didn't know he was going to do that. I learned that from mass media. So as far as I know, he didn't reject a UFC offer—he just didn't give them any answer."

According to Finkelchtein and various sources close to the negotiation process who spoke to Bleacher Report on the condition of anonymity, the UFC's offer was the most lucrative one presented at the time. But Fedor turned it down.

Months later, Fedor said the core problem lay with the UFC's "one-sided" contracts, which limited his autonomy.

"The UFC contract was just draconian and oppressive," Fedor said in an impromptu Periscope session with a Russian sports outlet. "I'm not ready to sign such an enslaving contract. First of all, they should show respect for the fighters—the kind of respect I receive in Japan."

The joyous energy that surrounded the initial announcement of Fedor's return had withered, particularly following the disappointing announcement that he would face 2-0 Jaideep Singh in his first fight back. Fan support quickly transformed into unabashed resentment for one of the greatest fighters in the sport's history. Matters would only get worse from there.

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Following a lopsided victory against the inexperienced kickboxer Singh on New Year's Eve, Fedor shopped around for his next proposed matchup. Given that few promotions could pay his reported $2 million-per-fight asking price (per Russia's izvestia.ru), a new round of negotiations with the UFC made sense.

The UFC once again reportedly offered Fedor a lucrative deal, which he rejected to join forces with Eurasia Fight Nights (EFN), one of Russia's foremost MMA promotions.

Founded by Kamil Gadzhiev, the promotion, known for its pageantry and bizarre production values, was mainly funded by Dagestani oligarch Ziyavudin Magomedov. The billionaire paid Fedor's purse to compete against UFC veteran Fabio Maldonado on June 17, 2016. Ironically, the event was available on the UFC Fight Pass, the promotion's subscription service.

Yet after Fedor signed his one-fight deal with EFN, he appeared on The MMA Hour to tell Ariel Helwani that he was "much closer" to a UFC deal than ever before. While many pundits believed Fedor because he was already competing on UFC Fight Pass through EFN, it soon became clear the heavyweight was leveraging promotions against each other to ensure the largest possible payday.

Each time the UFC offered Fedor a deal, he would inform the media, which naturally created a stir within the community. He would then leverage that information against other promotions keen to strike a deal with the Last Emperor. This eventually secured larger fight purses from Rizin and EFN, according to a source close to Fedor.

What Fedor hadn't accounted for, however, was a difficult matchup against Maldonado. Fedor appeared slow and lethargic in the fight, and he was dropped once and staggered repeatedly in the opening round.

While the heavyweight somehow survived the onslaught and eventually won a highly controversial decision in his native country, he hadn't been able to dominate a 36-year-old who'd had his best days as a light heavyweight and had been released the prior year by the UFC after losing three of his last four fights.

The Last Emperor's stock dropped considerably.

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During the Bellator 165 event in San Jose, California, on November 19, the promotion interrupted the regulated violence to announce a heavyweight showdown between Matt Mitrione and a mysterious opponent. Moments later, Fedor Emelianenko emerged from behind a cloud of smoke, dressed in his trademark striped sweater and with a smirk painted across his face.

The sweater—a hodgepodge of green, beige and blue in horizontal patterns—had once been a staple of Fedor's attire, though he had not worn it publicly in several years.

"I'm happy to be fighting in Bellator," he told the gleeful crowd. According to Coker, the Strikeforce founder who had become president of Bellator in 2014, Fedor hadn't needed to be coerced away from the UFC. It was a mutual agreement.

"Honestly, the signing of Fedor was pretty organic," he said. "We didn't engage in any sort of conversations with him while he was with Rizin. Our talks started with him coming out and taking part in our Fanfest, then eventually evolved into fight talks. It took us months of negotiating. It's always tough when you have the distance issue, the language issues and cultural issues."

Following a decade of failed negotiations, blame games and outlandish statements from both sides, it appeared as though the rivalry between the UFC and Fedor had finally come to a disappointing dead end. Between the Bellator signing and new UFC ownership with different interests, Fedor is unlikely to set foot inside a UFC Octagon. One of the sport's greatest fighters has never competed in the most established organization on the planet and will never be inducted into the UFC Hall of Fame despite his unparalleled stardom. He'll likely never don UFC gloves on a PPV broadcast.

The inability to sign Fedor to the UFC will be remembered as one of Zuffa's biggest shortcomings. While pride and egotism factored into the decadelong struggle, it was eventually a lack of contractual flexibility and respect that put an end to years of negotiations.

"Someone who says a lot of negative things about you and then turns around and invites you to join him, how do you react to that? And it's not even about money," Fedor said in 2015, per Mindenhall. "It's all about mutual respect, meeting each other halfway."

Fedor and the UFC were never able to meet halfway. Unlike Captain Ahab, who eventually found his white whale and suffered its wrath, the UFC sails on, left to tell tales of what might have been.