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Road maps to 2020 megafights for Conor McGregor and Jorge Masvidal

Conor McGregor would like to stay busy in 2020, but what will that look like? Jeff Bottari/Zuffa LLC via Getty Images

There's still one month left in 2019, but the UFC is already in the process of booking its first quarter of fights for 2020.

And as we head into the new year, two of the biggest names in the sport -- the two names it seems, everyone has their eyes on -- are the newly crowned BMF champion Jorge Masvidal, and -- of course -- former two-weight champion Conor McGregor.

Each has a long list of potential megafights in 2020, including the possibility of facing each other. At the moment, Masvidal likely will take some time to let a few bouts play out. With McGregor, there's hope we could see him return to the Octagon as soon as Jan. 18, possibly against Donald "Cowboy" Cerrone.

So, as we wait to see how it unfolds, let's have some fun with some good old-fashioned speculation. Let's assume McGregor will return in January, and for the sake of speculation, let's assume that return will be successful. Here are the biggest fights for McGregor and Masvidal ... and what it would take to arrive at each one.

Conor McGregor vs. Jorge Masvidal

Why it might happen: After Masvidal beat Nate Diaz for the "BMF" belt on Nov. 2, McGregor dropped a hint on social media that he might be interested in fighting Masvidal. And although Masvidal has been skeptical about McGregor's willingness to face him, that fight would be worth a lot of money for everyone involved. And fights like that are always possible.

What would it take to get there: McGregor forcing the issue. It's probably not a fight the UFC is going to pursue on its own. The promotion has other options for McGregor that, frankly, would make more sense and sell just as well. But if McGregor were to come out and demand Masvidal, that would immediately become the fight to make.

Chance it will happen: You'd think McGregor expressing interest in the fight would be enough to book it, but we've seen McGregor express interest in plenty of fights this year, none of which came to fruition. Again, the chances of this happening come down to how loudly McGregor calls for it. And if I had to bet, I don't think you'll see McGregor call for Masvidal in January. Why would he limit himself to that one option when he knows the UFC is booking a lightweight title fight between Khabib Nurmagomedov and Tony Ferguson in March/April.

Conor McGregor vs. Khabib Nurmagomedov 2

Why it might happen: The UFC has a lot of incentive to book this fight. Think: a pile of cash. The first fight between McGregor and Nurmagomedov, in October 2018, reportedly generated nearly 2.4 million pay-per-view buys in the United States and Canada -- the largest number in UFC history.

What would it take to get there: If Nurmagomedov beats Ferguson in the spring, you know the UFC is going to look at this option. Nurmagomedov has said he wants McGregor to win "10 fights in a row" before granting him a rematch, but we all know his actual path to the title will be much shorter. The road map to this fight, believe it or not, might consist only of each of them winning his next bout and then getting paired against the other next fall. It would also require McGregor wanting to wait a bit for it, as Nurmagomedov will take time off in late spring for the Muslim fasting month of Ramadan and has said he doesn't want to fight in Las Vegas anymore, where he was suspended for a postfight brawl in 2018.

Chance it will happen: Decent. Very decent. Nurmagomedov's plans don't include McGregor at the moment. He's not lying when he says he has no interest in a rematch. But if McGregor looks good against Cerrone and makes enough noise -- which he's good at doing -- fans are going to want this. And the UFC will want to give it to them.

Conor McGregor vs. Tony Ferguson

Why it might happen: At the moment, no one is talking about this fight -- but believe me, that would change in an instant if Ferguson beats Nurmagomedov in the spring. Immediately, new fans to the sport would want to know about "the guy who beat Khabib." And what they'd find would interest them. Ferguson used to be managed by the same company as McGregor, and he suspects that company might have kept him away from McGregor in the past. It would be a brand-new matchup for McGregor, with a title on the line.

What would it take to get there: Even though there's no heat behind this matchup now, the path to get there is simple. Ferguson beats Nurmagomedov. Ferguson vs. McGregor would be an obvious candidate to headline that annual July event in Las Vegas, with Nurmagomedov poised to fight the winner at the end of the year.

Chance it will happen: Whatever you believe Ferguson's chances are of beating Nurmagomedov.

Conor McGregor vs. Nate Diaz 3

Why it might happen: As I've said since their second fight in 2016, a trilogy bout between McGregor and Diaz is always on the table. McGregor promised there would be one even before he evened the series at 1-1 more than three years ago. It's a fight that sells itself and is almost guaranteed stylistic fireworks.

What would it take to get there: Nurmagomedov beats Ferguson in March/April and refuses to fight McGregor in the near future. In that case, whom does McGregor fight? Masvidal? Or Diaz? I kind of lean Diaz. And I think the UFC would actually lean Diaz. Masvidal is a legitimate welterweight title contender. McGregor is a lightweight. McGregor is familiar with Diaz and would know exactly what he was signing up for against him. His team has always been in favor of a third fight. If it came down to Masvidal or Diaz, I think McGregor would pick Diaz.

Chance it will happen: I always like the chances of McGregor vs. Diaz 3. I just don't think their careers will end without settling this rivalry once and for all. And if McGregor's path to a title is blocked, why not do it in 2020?

Jorge Masvidal vs. the winner of Colby Covington vs. Kamaru Usman

Why it might happen: It makes competitive sense, for one. Masvidal is deserving of a title shot, coming off his spectacular 2019. There's a backstory between Masvidal and Covington, as they were former friends and even roommates. Usman and Covington fight at UFC 245 on Dec. 14, and Masvidal's name will be attached to that fight every step of the way.

What would it take to get there: It really comes down to Masvidal wanting it, which he should. He's been in the UFC since 2012 and has never fought for a championship. The only thing that would get in the way of this, really, would be if McGregor really called Masvidal out. Then he'd have to pick between the two.

Chance it will happen: High. If Masvidal were to capture the title in 2020, he would hold all the cards. He'd be a bona fide superstar and he'd control the title. He could call his shot at that point. I believe this is where we're headed in the first half of the year.

Jorge Masvidal vs. Nate Diaz 2

Why it might happen: Masvidal won the BMF belt at UFC 244 when a doctor stopped the bout because of a cut over Diaz's right eye. The ending left a sour taste in the mouths of fans and Diaz -- and even Masvidal, to a lesser extent. It was a successful main event the first time, and it would be again. You could hold it on the West Coast this time, too. Diaz's turf.

What would it take to get there: Masvidal winning the belt and calling Diaz out. I don't think we're going to see this matchup until we've seen Masvidal in a different matchup first. You can have a rematch of the BMF title fight, just not an immediate one. If Masvidal were to claim the 170-pound title and demand, as champ, his first defense be against Diaz -- to remove any doubt over what happened in the first one? We could see it again.

Chance it will happen: This one is interesting because it could definitely happen, but -- again -- I don't think it will happen next. It requires certain dominoes to fall. For now, I'll bet against it. They'll each move on to big fights, but not against each other.

Jorge Masvidal vs. Nick Diaz

Why it might happen: Could the older brother of Nate Diaz, who hasn't fought since 2015, return to the Octagon to avenge Nate's UFC 244 loss? What a story. Nick Diaz is an OG and a star himself. Masvidal respects him and has wanted to fight him for a long time.

What would it take to get there: It would require Nick being serious about a return, which, until he has signed a contract to come back, is speculation. In a recent interview with ESPN's Ariel Helwani, Diaz commented on potentially evening the score with Masvidal after his brother's loss, but the fact is he hasn't fought in nearly five years and hadn't talked about a comeback before that appearance. Additionally, the UFC would have to get on board with a fight between a legitimate title challenger and someone who hasn't won since 2011.

Chance it will happen: You can't count it out. If Diaz is serious about wanting it, it's a real option for a big fight. But I'm not convinced we're close to a Diaz return. I think Nick was asked about his brother's loss and, in that moment, he responded exactly as you'd expect a lifelong fighter to respond. That, to me, doesn't guarantee he's coming back.