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Jon Jones defends his light heavyweight title against Thiago Santos in the main event of UFC 239 in Las Vegas on Saturday
Esther Lin, MMA Fighting

Jon Jones and Amanda Nunes, arguably the most dominant man and woman to ever compete in MMA, will be in action at UFC 239 in bouts that will have distinctly different impacts on their respective legacies.

For Jones, he faces a respected and dangerous challenger with a few caveats. While no one questions the finishing power of Thiago Santos, the fact remains that he was previously thought of as a career middleweight capable of generating highlights without actually marking himself as a serious contender. Now, “Marreta” has the chance to turn the light heavyweight division upside down with one perfect performance.

Should Jones come out on top as expected, it will be seen as a routine notch on his belt, a reminder of his unwavering in-cage excellence even if it doesn’t necessarily add a significant chapter to his story.

Nunes on the other hand can vanquish one of the last remaining marquee names in the bantamweight division. She’s coming back down from 145 pounds, where she toppled the great Cris Cyborg, and her 135-pound reign already includes wins over Ronda Rousey, Miesha Tate, and Valentina Shevchenko. Taking out Holly Holm—the woman who famously KO’d Rousey all those years go—would put Nunes in the same place as Jones, in a nearly unassailable castle where the next notable challenge does not appear to be anywhere on the horizon.

In other main card action, Jorge Masvidal faces Ben Askren in a welterweight grudge match, Luke Rockhold makes his UFC light heavyweight debut against Jan Blachowicz, and Diego Sanchez looks for his longest winning streak in a decade when he meets Michael Chiesa in a welterweight bout.

What: UFC 239

Where: T-Mobile Center in Las Vegas

When: Saturday, July 6. The three-fight early preliminary card begins at 6:15 p.m. ET and will air on ESPN+, followed by a four-fight preliminary card on ESPN at 8 p.m. ET. The five-fight pay-per-view main card begins at 10 p.m. ET and is available for purchase exclusively through ESPN+.

Jon Jones vs. Thiago Santos

Once upon a time, when Jon Jones was booked to fight Anthony Johnson, fans could envision a scenario where the one-shot kill potential of “Rumble” would make him the man to hand Jones his first true defeat. That bout fizzled due to Jones’s well-documented legal travails, but four years later Jones again finds himself facing a challenger renowned for their accurate and deadly strikes.

There are parallels between Johnson and Thiago Santos, Jones’s latest challenger. Like Johnson, Santos is a former welterweight (how?) who eventually made the move to 205 pounds where he didn’t appear to lose any of his power (unlike Johnson, Santos had a successful run at 185 pounds before eventually trying his hand at light heavyweight). If anything, cutting less weight has appeared to give Santos the best of both worlds when it comes to taking advantage of his speed as well as his strength. Santos was such a feared middleweight because of his ability to throw ridiculously damaging punches and kicks from seemingly out of nowhere.

It just isn’t anything that Jones hasn’t seen before. Maybe Santos’s propensity for unpredictable spinning attacks will warrant added caution, but Jones is arguably the greatest defensive fighter in the sport and it’s easier to kick the cap off of a bottle (topical!) than to catch him with anything clean when he’s on point.

Being able to launch one-hitter quitters doesn’t do you much good if you can’t land that one hit. Jones will avoid the best shots Santos has to offer until he can use his superior grappling to ground Santos and bully him on the mat, eventually earning himself a TKO in the second or third round.

Pick: Jones

Amanda Nunes vs. Holly Holm

Styles make fights, as they say, and there’s certainly a compelling argument to be made that Holly Holms’s methodical striking and big-game experience will go a long way towards pulling off an upset on Saturday. Holm has never had a problem going five rounds inside the Octagon. She has, however, had problems winning those rounds.

In three five-round UFC fights that have gone the distance, Holm is winless (and that’s not even including her fight with Miesha Tate, where Holm was finished with less than two minutes remaining in round five). Despite having a reputation as a point fighter, she hasn’t had much luck scoring points with the judges.

That’s why I have to pick Nunes here, even if Nunes doesn’t become the first woman to knock Holm out. “The Lioness” showed in the Pennington and Shevchenko fights that she knows how to pace herself in a five-round fight, and while she doesn’t always shine in every round, she also won’t wilt in the final lap especially against an opponent like Holm who isn’t exactly known for her fast-paced offense.

Nunes might not win the volume battle, but the power punches she lands will tilt the scorecards in her favor when all is said and done.

Pick: Nunes

Jorge Masvidal vs. Ben Askren

You know Jorge Masvidal would love nothing more than to serve up a three-piece and a soda or a family pack with a two-liter soda or whatever other specials happen to be on the menu at Chez Gamebred this week. Too bad he’ll probably have to settle for plain old ground beef.

Versatile and tough as he is, a dedicated wrestling attack has proven to be Masvidal’s foil on several occasions. Back in May 2017, he ran into the human backpack Demian Maia, who did little damage but neutralized much of Masvidal’s offense with his grappling en route to beating Masvidal by split decision. Masvidal has plenty wrestling of his own to work his way out of bad spots, but he’s never faced a takedown artist on the level of Ben Askren before.

Simply put, Askren will find a way to put Masvidal on his butt, and even if he can’t keep him down, he’ll reset and chain wrestle his way to takedown after takedown. It’s a strategy that will undoubtedly frustrate Masvidal (and fans hoping that Masvidal will beat Askren down) and allow Askren to do what he does best, which is win rounds. In the eyes of the judges, pitter-patter strikes from top position are better than nothing.

Were this a five-round fight, I would actually favor Masvidal, trusting that he would eventually find his rhythm and start to dissect Askren in the later frames. But it isn’t and all Askren has to do is win two of the three rounds, which I expect him to do, even if it isn’t pretty.

Pick: Askren

Luke Rockhold vs. Jan Blachowicz

Askren-Masvidal might have the most intrigue, but this matchup is the toughest to pick if only because we don’t know what to expect from Luke Rockhold at 205 pounds. And in Jan Blachowicz, the UFC didn’t give him an opponent who will give him much room to feel things out.

I’m of the camp that Rockhold’s cut down to 185 has long had a deleterious effect on his chin. Yes, there are questions about his defense that simply eschewing a weight cut won’t solve, but he’s earned the benefit of the doubt with his strong performances outside of the losses to Romero and Bisping. Critics seem to forget that Rockhold is a premier fight finisher with wicked chokes and heavy ground-and-pound, in addition to having a solid kickboxing base.

Blachowicz doesn’t really have the kind of explosive punching power that should have Rockhold feeling too threatened (then again, the same was said about Michael Bisping before Rockhold’s ill-fated rematch with him), though he has more than enough pop to put Rockhold down if the former middleweight champion isn’t careful.

Much of my faith in Rockhold winning here is based around him being able to absorb more punishment due to being less dehydrated. So don’t let me down, biology!

Pick: Rockhold

Diego Sanchez vs. Michael Chiesa

Would you bet against a Diego Sanchez who 1) has apparently learned the secrets of “anti-aging” and 2) is an actual Jedi?

If you’re picking Sanchez here, it’s because of his legendary gas tank that at this point is running on a one-of-a-kind concoction of Mexican NOS and actual insanity, plus the fact that he’s never been submitted, which bodes well for Sanchez given that Chiesa is a submission specialist.

But Chiesa has great cardio too and has never lost when going the distance. He’s a better striker than Mickey Gall (the last fighter that Sanchez overwhelmed) and also more experienced and disciplined on the ground. His aggressive top game will render Sanchez’s wild scrambles mostly ineffective. The key for Chiesa here will be to make sure there is no opening for the judges to possibly give the fight to Sanchez, who will be emptying the clip until the final buzzer sounds.

This will be an absolute dogfight for 15 minutes, and while I’d love to pick Sanchez, I’m going with Chiesa to kick off what should be a sweep for the main card favorites.

Pick: Chiesa


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