Why Conor McGregor’s retirement is a perfect time to bet against him

For the third time in 50 months, Conor McGregor has retired.

The first time he quit, the reactions were genuine: Whoa, is this real? Is he done?

The second time: He’s probably coming back … right?

Then, this weekend, the collective reaction to McGregor tweeting his retirement was a shoulder shrug. McGregor is hurtling into Brett Favre territory faster than one of his patented rear leg front kicks.

Nobody believes McGregor, of course. The last two times McGregor “retired” — April 2016 and March 2019 — it was painfully obvious he used the moment as a negotiating ploy to get paid for his next fight. So why would this time be any different?

You can still bet on McGregor and his next fight, because anyone who follows the sport knows his heart is in the Octagon and he’ll return sooner than later.

In a rematch between McGregor and Khabib Nurmagomedov, the recently-retired Irishman is a massive +260 underdog — and it’s the most anticipated fight in UFC right now.

Bad blood between the two? Check. The post-fight brawl in the ring in October of 2018 after McGregor submitted in the 4th round was nearly as shocking as the match.

Money to be made? You bet. UFC 229 featuring their showdown was the highest-selling UFC event of all-time. McGregor knows the rematch would shatter PPV numbers, so why not hold out for the payday you deserve?

Either way, I can already tell you this: I’ll be betting against McGregor in the rematch, even at the steep price of -400 for Khabib. Nurmagomedov is simply too good. He’s younger, faster, and stronger than McGregor, and still undefeated at 28-0.

In fact, this dovetails nicely into my betting strategy against McGregor. The general public loves him. He’s a cultural phenomenon — his retirement tweet last weekend generated more publicity than the entire UFC 250 card — who the public will back just like they did against Floyd Mayweather.

Besides the inactivity for McGregor — since the loss to Nurmagomedov in October of 2018, he’s had just one fight, and it was a :40 beatdown of Donald Cerrone — he’s largely coasted since pocketing over $30 million from the fight against Mayweather. The legendary boxer Marvin Hagler famously said: “It’s tough to get out of bed to do roadwork at 5 am when you’ve been sleeping in silk pajamas.”

Nurmagomedov is well-known in the fight community, and even though he’s an Instagram star in Russia, he doesn’t have nearly the recognition from the general betting public. Nor has he profited the way McGregor has. You can’t quantify it, but in the “who wants it more” category, that’s all Nurmagomedov. The -400 actually seems short, and I’d expect professional money to come in on Khabib.

Thing is, I don’t think McGregor’s first match post-retirement would be against Nurmagomedov. Too challenging, and there are too many question marks across the UFC landscape, with Justin Gaethje standing as the interim lightweight champion and poised for a unification bout with Nurmagomedov.

The safer bet, for McGregor at least, would be round three against Nate Diaz. Diaz is one of the toughest guys in the welterweight division, but he turned 35 in April. The last time he fought, his right eye was so badly damaged by Jorge Masvidal, that Diaz needed 25 stitches and plastic surgery.

McGregor would be a considerable favorite (-250) against Diaz. I’m not really looking to bet on McGregor after a third retirement, but it’d be difficult to pick against McGregor in that fight.

Then again, we’re not talking about the mid-2010s McGregor, who in his prime lost to Diaz in March of 2016 and then quickly had a rematch five months later and was victorious. Conservatively, he’s pocketed nine figures since those days, and once you get to the mountain top, you get more selective because you can be.

Those two fights would move the needle the most for McGregor, unlike potential battles against Jorge Masvidal (-143) or Justin Gaethje (+115). It seems unlikely McGregor would announce a retirement to set up a fight against either of those two — but if that’s how things were to shake out, again, I’d be all over McGregor’s opponent.

So all signs point to McGregor un-retiring and returning later in 2020 or perhaps early 2021 to fight Nurmagomedov. And whatever the line is when the fight is announced, you want to fade McGregor.