I want to believe the Tony will be able to use his striking skills to his advantage to make Khabib hesitant and potentially hurt him during standup exchanges.
I would love to see Tony use his BJJ to create scrambles, reversals and maybe even a submission...
But
When trying to accurately assess what I expect from a matchup I generally start by envisioning each fighters style, how they move, the techniques and tendencies they use most frequently, and then I do my best to imagine how those things would play out.
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Khabib has the best overall ability to secure takedowns and keep his opponents down of anyone I have ever seen in the modern era of MMA. He maintains excellent posture on the ground, he is usually on his feet (not his knees) and he has explosive and highly effective guard passes, generally to half guard where I feel he does his best work.
Even though Tony is a wrestler he has shown he can be taken down. There are two primary reasons for this:
1) his style is wild and he leaves himself in awkward positions (frequently happens during "spinning shit")
2) he generally doesn't mind going to the ground, even on his back because he has confidence in his BJJ
Unless Tony can hurt Khabib on the way in (which is possible but not going to be easy) I see this fight playing out like most other Khabib fights. On the ground with Khabib on top...
now here is the X factor:
Can Tony keep Khabib from passing guard? (I don't think he will be able to do so all night)
Will Tony be able to create scrambles? Will he be able to get on top?
Tony has EXCELLENT submissions. He is lethal. I think of him as a Frank Mir/ Werdum/Maia type BJJ finisher (slightly less variety as Mir and not quite on these guys level but close when it comes to MMA submissions)
Two of Tony's 9 submission wins were via triangle, a sub generally set up on the bottom in full guard, hence the importance of keeping Khabib from passing guard.
Tony is an Eddie Bravo protege 10th Planet BJJ student, tends to use rubber guard a lot. I have done a bit of BJJ myself and since I have well above average hip flexibility (especially for a big guy), I liked to use rubber guard...
The issue with rubber guard is that if you can't trap the opponent they often get a fairly easy pass to half guard or side control and Khabib is very good at passing to half guard.
People have been questioning Khabib's cardio as this will be a 5 round fight, but I see him being in dominant positions most of the fight, even though he is very active with ground and pound, the damage he inflicts should outway the energy he expends. And he lost a bit of muscle for the Barbosa fight making his weight cut easier and leaving less muscle to drain oxygen.
I'd love to see Tony pull off a sub, but Khabib gets most of his TDs from the clinch; Tony tends to get his d'arce choke in place while stuffing a takedown from a shot.
I am a huge fan of Tony as a fighter, he is exciting and he is a finisher with great heart. He is going to need his cardio and his heart in this one.
I give Tony basically a puncher's chance (and more realistically the submission equivalent of that phenomenon), but even that won't be easy because Khabib is always in dominant positions. The fact that Khabib stands 90% of the time on the ground makes it tough to drag him into a triangle, an armbar is possible but that pretty much goes away in side control or half guard.
I think Tony's best bet is to either catch Khabib on the chin coming in, then maybe ground and pound or take his back, or find a way to hit a sweep. He should be drilling half guard sweeps like crazy, he should bring in Nogueira, he should work his de la riva guard which would be the perfect answer to Khabib standing up while on top on the ground. Tony should also drill heel hooks and leg locks to take advantage of Khabib's frequent standing in guard.
Tony can pull it out but I expect he would have to do so by being opportunistic, a la vintage Big Nog or Anderson/Chael 1 (but Khabib won't make it that easy to get wrist control and won't be laying down on his chest like Chael was)
That or be able to keep it standing as I think Tony will have a huge striking advantage, but that is easier said than done and Khabib has ragdolled some excellent grapplers already.