Five Questions with Phil Chertok: The UFC 239 Edition

Phil Chertok discusses the UFC 239 card this weekend featuring Jon Jones vs. Thiago Santos, Amanda Nunes vs. Holly Holm, and the Hall of Fame.

This Saturday night, the UFC presents UFC 239 from the T-Mobile Arena in Las Vegas, Nevada.

While International Fight Week has gone through modifications and adjustments, this year’s version features one fight card and the annual Hall of Fame ceremony.

Two championship fights headline this weekend’s card as Jon Jones returns to the octagon for the third time in seven months following victories over Alexander Gustafsson and Anthony Smith. Once again, he is a sizable favorite as he takes on Thiago Santos, who competed at middleweight and has brought his power to the weight class.

In the other title fight, Amanda Nunes looks to build on her already impressive career as she faces the 37-year-old former champion, Holly Holm. It’s a big fight for the former boxer, who has struggled since losing her championship to Miesha Tate in March 2016. Holm last fought in June of 2018 and presents many challenges for the champion, who has not suffered a defeat since September 2014.

Here are this week’s five questions for POST Wrestling’s Phil Chertok heading into the weekend:

POST: Is there any element of Thiago Santos’ game that you feel people are overlooking or does this fight with Jon Jones play out in the same way the odds are positioned?

Chertok: At this point in his career, Jon Jones has faced the best of the best in the Octagon and it’s hard to pick out anything that Santos does better than Jones’ previous victims. Santos is going to be hungry going into the biggest fight of his career, but Jones has crushed the dreams of many title challengers before and I expect this to be no different.

Heading into the women’s bantamweight title fight, many already believe Amanda Nunes is the best female fighter of all-time, but what does this fight represent for Holly Holm?

Holly Holm will always be known for her iconic knockout of Ronda Rousey but her 3 losses in title fights since could make that the only memory fans keep of her. A win over 2 division champion Amanda Nunes would change the narrative from Holm being known as the woman who beat Ronda, to the Preacher’s Daughter being recognized as one of the all-time greats herself.

Do you like Luke Rockhold moving up to light heavyweight and how far is he from a title fight, if he is victorious over Jan Blachowicz? 

I always like the idea of fighters fighting closer to their natural weight and Luke Rockhold’s experience sparring AKA teammates Cain Velasquez and Daniel Cormier should mean that he fits right in at 205. Jan Blachowicz is a very tough challenge for Rockhold’s first foray into light heavyweight and a win would be a strong statement. Despite a good number of prospects, the division is lacking named contenders and being a former champion, Luke would probably be the biggest draw in a potential matchup vs Jon Jones. Because of that, I could see Rockhold getting a shot with 1 more win after Saturday night.

Given what you saw in Ben Askren’s fight with Robbie Lawler, what type of fight are you expecting with Jorge Masvidal?

I expect a similar type of fight with Askren moving forward relentlessly looking to tie up Masvidal and Gamebred looking to make him pay constantly with knees and short shots as Ben closes the distance. It’s going to take a lot of firepower to stop the two time Hodge Trophy winner from constantly advancing but if anyone has a shot it’s Jorge Masvidal, who’s proven to be one of the most durable fighters at any weight.

Michael Bisping is the headliner for the UFC Hall of Fame ceremony on Friday night, is there a memory that stands above the rest for you regarding Bisping?

Unfortunately for Michael Bisping, some of his most memorable moments don’t show him at his best. Be it spitting at Jorge Rivera’s corner after finishing him, getting put to sleep by returning legend George St-Pierre or getting flat-lined by Dan Henderson in one of the most replayed knockouts in UFC history, the Count has had some tough times in the Octagon. He’s also had some glorious moments including winning the Ultimate Fighter, becoming UFC middleweight champion by knocking out one of his biggest rivals Luke Rockhold and the one that stands out most for me, defeating another future UFC Hall of Famer, Anderson Silva at home in London. At that point in his career, it was uncertain if Bisping would ever get a title shot and defeating The Spider, a legend and former champion felt like a title win for the Brit, especially since he did it on home turf. Bisping’s storied career inside the Octagon makes him a no-brainer for the Hall of Fame and his skills outside the cage as an analyst and broadcaster mean that we get to enjoy his presence for years to come.