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Charles Oliveira, who is set to face Islam Makhachev in October for the vacant UFC lightweight title, is arguably the best 155lber on the planet right now.
Is Charles Oliveira the greatest lightweight in UFC history, though, or are there some fighters from the promotion’s past who could’ve beaten him in their prime?
Obviously it’s an impossible debate to truly decide, as none of these fighters will be able to face ‘Do Bronx’ in the near future. Stylistically, though, at their best, it’s fair to say that they’d have stood a fair chance of defeating the Brazilian.
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Here are five UFC lightweights who could’ve beaten Charles Oliveira in their prime.
#5. Charles Oliveira vs. Tony Ferguson
Given that Charles Oliveira completely dominated Tony Ferguson when they faced off at UFC 256 in late 2020, the idea that ‘El Cucuy’ belongs on this list might seem a little strange.
However, the fact is that the Tony Ferguson who faced ‘Do Bronx’ was not the same Ferguson who cut a path of destruction through the lightweight division from 2013 to 2020, putting together 12 straight wins in the process.
The ‘El Cucuy’ who fought Oliveira was coming off a devastating loss to Justin Gaethje. He seemed to have aged overnight, an idea that can be supported by the fact that he’s now lost five bouts in a row.
In his prime, though, Ferguson was an absolute monster. Not only did he have a tremendous striking game, but the pace he was able to push could cause almost any foe he faced in the octagon to wilt, even ultra-tough fighters like Rafael dos Anjos and Anthony Pettis.
More to the point, Ferguson’s takedown defense and submission defense were both fantastic. His chin was also seemingly unbreakable, as we saw when he survived huge shots from Pettis and Lando Vannata.
Oliveira would undoubtedly have given prime Ferguson a tricky fight purely due to his insane grappling skills. Overall though, whether he could’ve gotten ‘El Cucuy’ to the ground is questionable. At his best, Ferguson would’ve had the edge standing, giving him the advantage.
#4. Charles Oliveira vs. Anthony Pettis
While we did see a featherweight fight between Charles Oliveira and Anthony Pettis in 2016, with Pettis winning via submission, it’s probably fair to say that neither man was quite at their peak at that point.
‘Do Bronx’ was still developing and certainly wasn’t the monster that he is today. Pettis, meanwhile, had dropped down to 145lbs in an attempt to rescue his career after suffering three straight losses at 155lbs.
Could the ‘Showtime’ that held the UFC lightweight title from 2013 to 2015 have overcome the Oliveira that we know and love these days, though? It definitely would’ve been possible.
Firstly, as seen in their 2016 bout, Pettis possessed a highly underrated submission grappling game. At his peak, he rarely found himself in trouble on the ground. Most of his opponents tended to attempt to simply control him from the top – something that just isn’t in Oliveira’s nature.
On the feet, meanwhile, while ‘Showtime’ never possessed an iron chin, he was also able to avoid the majority of his opponents’ attacks with his speed and movement. He could also unleash an array of wild strikes from seemingly any angle, all with knockout power.
A fight between prime Pettis and the ‘Do Bronx’ that we see competing today would’ve been massively entertaining, and it also would’ve been a tricky fight to pick. However, there’d definitely be the chance that ‘Showtime’ could’ve pulled off the win.
#3. Charles Oliveira vs. Benson Henderson
It’s arguable that of all the fighters to hold the UFC lightweight title over the years, Benson Henderson is the most underrated. Sure, his career hit a slide when he moved to Bellator MMA in 2016, but his UFC career saw him go 10-3, with his only real losses coming against Anthony Pettis and Rafael dos Anjos.
At that point, ‘Smooth’ was already battle-hardened, and it’s arguable that he was slightly past his prime, too.
During his peak years, though, Henderson put together a winning run of seven fights that led him to the top of the mountain. At his best, he seemed nearly impossible to defeat.
‘Smooth’ wasn’t the best striker, wrestler or submission grappler, but he seemed to blend the three together better than anyone else. He’d often go right into the wheelhouse of his opponents to defeat them – outscrambling Frankie Edgar, for instance, and destroying Nate Diaz on the feet and with ground-and-pound.
Most importantly, in a hypothetical fight with Oliveira, Henderson was almost impossible to submit in his prime, escaping some ridiculous situations in his fights with Jim Miller and Donald Cerrone in particular.
Overall, this would’ve been a hugely difficult fight for even the ‘Do Bronx’ of today, and it’s possible that Henderson’s pace and all-round skills could’ve won him the day.
#2. Charles Oliveira vs. BJ Penn
While his UFC career ended in truly dismal fashion, with seven largely one-sided defeats in a row, BJ Penn is still widely regarded as one of – if not the – best lightweights in MMA history, and for good reason, too.
Unlike other dominant UFC champions such as Anderson Silva and Georges St-Pierre, Penn’s reign as lightweight kingpin didn’t last that long. He captured the vacant title by beating Joe Stevenson in 2008, and made just three successful defenses of it before falling to Frankie Edgar in 2010.
Despite this, though, Penn was a remarkable fighter who became more renowned for being able to step up in weight and defeat far larger opponents rather than remain dominant in a single weight division.
More to the point, his style was largely ahead of its time. At a point where most fighters had one or two areas of strength at most, ‘The Prodigy’ possessed a top-notch boxing game, was a world-class Brazilian jiu-jitsu black belt on the ground, and was also near-impossible to take down, even for powerful wrestlers.
So could the version of Penn that torched Kenny Florian and Diego Sanchez have beaten today’s iteration of Charles Oliveira? ‘Do Bronx’ is undoubtedly a great fighter, but it’s hard to imagine him toppling peak Penn.
Not only did ‘The Prodigy’ possess top class offensive skills, but when you add in a granite chin and his ridiculous takedown defense, it’s hard to imagine what ‘Do Bronx’ could do to beat him.
The likely outcome to such a fight would probably have seen Penn preventing any takedowns and simply outboxing Oliveira with his jab before putting him away with something nasty on the feet. At his best, the Hawaiian would have simply been a nightmare opponent for the Brazilian.
#1. Charles Oliveira vs. Khabib Nurmagomedov
Many UFC fans are hugely excited about the upcoming lightweight title bout between Charles Oliveira and Islam Makhachev. One of the reasons why is that it seems to be the closest thing we’ll ever get to a clash between Oliveira and Khabib Nurmagomedov, who retired in 2020 with an unbeaten record of 29-0.
However, the truth is that for as good as Makhachev is, he still hasn’t reached the same levels that ‘The Eagle’ did during his run as UFC lightweight champion.
Nobody had a takedown as quick and powerful as Khabib, and nobody was quite as capable of putting immense pressure on their opponents as the native of Dagestan. Even ultra-tough fighters like Dustin Poirier and Justin Gaethje couldn’t stop Khabib from bullying them in the octagon.
Of course, Oliveira also holds wins over Poirier and Gaethje. If anything, his record – which also features wins over Michael Chandler, Tony Ferguson and Kevin Lee – is superior to that of ‘The Eagle’.
But could the current version of Oliveira have beaten prime Khabib? To be frank, it seems doubtful. Sure, he’d have stood a chance of tagging him on the feet, but it’s unlikely that he’d have been able to prevent the Dagestani’s takedown.
Despite his excellent guard game, it’s also difficult to imagine a grappler as well-schooled as ‘The Eagle’ being caught with a triangle or a guillotine from the bottom.
Oliveira may well be able to overcome Makhachev in their bout next month, but if the UFC were to book a clash between him and Nurmagomedov tomorrow, he’d still come in as the underdog. In Khabib’s prime, it’s unlikely that ‘Do Bronx’ would’ve stood a chance.
