Which Middleweight fighter has the best style to beat UFC Middleweight Champion Anderson Silva?
Rousimar 'Toquinho' Palhares, and to a much lesser extent nowadays, Paulo Filho. In other words any BJJ ace with explosive takedowns.
As multi-faceted and skilled Anderson Silva is relative with everyone else that lives and breathes on this humble abode, he does have liabilities just like everyone (Fedor included) that would garner any prudent person to believe that, given the specific match-up, he can be defeated in an emphatic/speedy manner much like both Ryo Chonan and Daiju Takase can attest to. The main detriment in Silva's game lies in his defensive wrestling and sprawl, two things that are paramount for any fighter that has a decent shot at beating him because let's face it, the list of guys that can hang with Anderson on the feet, meaning just survive with him, are few and far between.
At one point that man appeared to be Dan Henderson, but choosing him as Silva's most stern match-up is downright silly. While Hendo can assuredly get Silva down, his biggest problem is maintaining a gameplan for the full duration of a fight. He'll often get right hand-happy, overcommit himself to that dynamite he calls a right hand and put his wrestling on the backburner in favor of the highlight reel KO. Against Silva that strategy leads to an imbroglio because not only does Silva have a hell of a chin (as witnessed in the Hendo fight after eating two massive overhand rights and simply taking one step back) but he wasn't fazed at all in their first encounter and it was Hendo that careened to the mat after their first big exchange. If you're in a gun fight against Silva, odds are firing away with your one Suzy Q for an answer won't be the destined formula for success.
It's hard for guys to get inside Silva's long right jab and teep, and when someone like Hendo is coming in with zero defense insofar as using his chin as a catalyst (even though his jaw is made of granite) to absorb all the punishment he'll take just to deliver that one right hand, it spells disaster.
With that said, the worst possible style match-up for Silva is the following: An elite BJJ player with powerful takedowns.
I can think of two guys that fit the bill, and one I believe certainly stacks up well on paper at least. Rousimar Palhares and Paulo Filho. Filho gets shit on for his performance against Sonnen and no one's familiar with Toquinho yet but both guys are the sort of fighter I see giving problems to Anderson. Not only is Toquinho strong as an ox, but he has incredibly powerful takedowns coupled with a very aggressive top game and good submission chops, particularly vicious heel hooks and leg locks, that would make Silva uncomfortable on the floor to say the least. Now before things get out of context, I don't believe Toquinho's current incarnation is the key to success against someone of Anderson's acumen, but if he continues to shore up his striking (a prerequisite against Silva) and improves his cardio which also appears to be a bit shoddy, I definitely believe he has the best chance of trumping the much malignant P4P regarded fighter.
Regarding Vitor, he doesn't have all the tools to beat Anderson. Sure he has good boxing and it's obviously improved during his tenure at Xtreme Couture but he's still too tentative for the most part and, improvements aside, he's seriously outgunned standing against Anderson. Also, he doesn't have the sort of top game to pass Silva's guard and give him a lot of problems if he takes him down. I could be very wrong, but I don't think so.
As for Lindland, I can't see him winning either. He can definitely take Anderson down if he gets within clinch range but he's got to set-up his clinches and shots with strikes or he'll never get in past Anderson's long right jab and teep. I just can't see him striking even marginally effectively with Anderson because he's not even as good as Hendo standing and Hendo had a hard time closing the distance with his strikes. He also doesn't have the chin to eat a whole lot of Anderson's leather either, and that's a major detriment because it's almost a guarantee that if you fight Silva, he's going to lay some shots on you.
The one advantage he does have on Hendo is that he's far more willing to turn a fight into a grinding wrestling match whereas Hendo will get right hand-happy, but I still don't think it matters much. I'd watch and it's still interesting but I think Anderson has to be a heavy, heavy favorite.
Now while Silva is a legit black belt under the Nogueiras' and great defensively, it's hard to see him staving off each and every sub attempt that an aggressive submission chaser like Toquinho will throw at him. Not only is Toquinho very tough to neutralize on top, but he can pass elite BJJ players guards like butter, and I wouldn't even place Silva in the latter. If Travis Lutter can pass Silva's guard (and at one point mount him) there's certainly dependable hope that Toquinho can cruise through a takedown and pass just as effectively. The one error, major at that, with Lutter was going for a sloppy armbar just enough to allow Silva to wade with defense in the quickness and turn the tables. Against Toquinho, Anderson will have to be weary of a few things, specifically Toquinho's crunching heel hooks.
Even more so because Silva's long limbs provide Toquinho with a greater window to license punishing submissions at his own expense. Add onto that, Ryo Chonan submitted Silva with a heel hook and while Anderson did go into that fight with a pre-existing injury, he had no answer. Mind you that was 4+ years and change ago, and Silva has clearly established overall improvement since then, but Toquinho's heel hooks present the sort of challenge I see giving Anderson problems if the fight were to ever hit the canvas.
I think given time, particularly for Toquinho to shore up his striking and improve his cardio, it's a very intriguing match-up and one I'd definitely be interested in watching. You'd have to make Silva the favorite for obvious reasons, but I'd give Toquinho as good of odds as anyone especially if he can get the fight down, which he should. Imagine if Lutter and Leites can comfortably take Silva down, how easily someone as explosive and powerful as Toquinho will succeed in that area. Silva's kryptonite match-up still remains to be seen, although considering he has laid eggs in the past and fallen deep into submission losses against much lesser competition, coupled with his less-than-stellar defensive wrestling, it isn't completely out of the norm to believe that someone with Toquinho's skill set can pull off the upset.