Ever since fighters have been passing into retirement, leaving behind their legacies to be appreciated, pondered and scrutinized, one of the most recurring questions is based around fights between men who are separated by time.
As fight fans, we need to have questions answered; it’s one of the reasons why consistent fighters have both fans and detractors in abundance. The fans believe most of the questions have been answered and the result is perfection in the form of their man, while the detractors say “not so fast,” and they continue to watch believing that one question remains, and when it is answered, that man will fall.
Of course, much of it is name recognition and the style vs. style debate, but all of it comes back to the fact that the question itself is transcendent: generation gap be damned, the question will be asked, and the answer debated until we are all tired and move on to the next hypothetical fight.
Still, we can take comfort in knowing we are not the only ones asking the question—the fighters do it as well; how could they not compare themselves to the greats of times past?
In that spirit, here are 12 fights that ponder the question.
When you consider just how many fighters hold the greatest of pride in their submission game and look to employ it over all other facets of MMA, the idea of seeing two men of like minds go at it is always fun to ponder.
Of course, we were supposed to see something like that when Matt Hughes took on Renzo Gracie, but what we got was a stand up fight instead. So in order to avoid this pitfall, a matching between Royce Gracie and Shinya Aoki—two fighters with little stand up skills who would much rather fight on the floor—seems the perfect remedy.
Both Gracie and Aoki are so brazenly proud of their ground games (and for very good reason) that it would seem to be a matter of pride for each man to test the other on the mat, and given how mean Aoki can be, and how stubborn Gracie can be, it could quite possibly turn into a barn burner.
Given how far the submissions aspect of MMA has grown, it would seem Aoki would have the advantage. He’s trained with some of the very best in the world, and today’s grappling seems more advanced and aggressive than the days when Royce ruled the sport.
But if Royce would have an advantage anywhere, it would be his command of the basics, and more often than not, the basics are what win fights.
Would Aoki be able to run all over Gracie, showing that the art of submissions has grown so much that it cannot be defined by a single name, no matter how great that name is?
Or would Gracie be able to take the day, proving that an armbar is still and armbar and that the fundamentals of a sound guard and a dedication to the basics of groundwork are transcendent?
Although my head says Aoki, my heart says Gracie, and the truth is probably somewhere in between.
When BJ Penn burst onto the scene, he seemed to have no limits save that of experience.
When he decided to let his hands go, people got knocked out easily. If their chin was level with his, his knee would find it and down they’d do. As a wunderkind new to the sport—with his acclaim based solely on his phenomenal jiu-jitsu game—his striking was utterly unbelievable; if he thought it, he could do it, seemingly without effort.
Gilbert Melendez is more of a gritty workhorse who would meet you in the middle of a raging river in order to fight you, and you’d be the first one to decide to walk away, even if you were winning.
Melendez is a tough, rugged customer with a solid grappling base and the will to throw as many punches as he takes, and he can take as good as he gives. He’s also incredibly consistent, capable of fighting hard for a full twenty-five minutes, totally dedicated to the fight.
It would be interesting to see if Melendez could take the kind of shellacking that Penn would put on him while standing in order to test his cardio and wear “The Prodigy” down with his wrestling. Penn possessed brutal KO power from a multitude of strikes, and again, his ability to touch his opponents however he pleased would mean Melendez would always be in danger.
I honestly think the early version of Penn—young and hungry and so explosive—would prove to be too much for Melendez, but I’d love to see it either way.
Given all the talk surrounding Chael Sonnen since his loss to Anderson Silva at UFC 148, one might think he’s the greatest man alive; he’s certainly been given the hype by the press.
But beyond all the hype is a single desire: to be the champion, for just one night. He said it in the primetime special before UFC 148, and the desire remains today.
He’s a great wrestler with great conditioning, on the title hunt. Odd as this may sound, we’ve seen his style before. In fact, we’ve seen it take the UFC welterweight championship and defend it four times, albeit in the form of a much better striker and submission artist.
The form of which I speak is Pat Miletich.
Both men are wrestlers and their game is grounded in wrestling. Granted, Sonnen is the better wrestler, but not so much that to make him seem like an entirely different species of fighter than Miletich.
On the flip side, both men enjoy striking, but Miletich was by far the better striker, not to mention submission practitioner.
This would be an excellent fight that would see both men tested, but in the end I feel Miletich would take the victory via doctor’s stoppage thanks to a constant barrage of punches that would open cuts on Sonnen’s face and above his eyes.
Miletich is an excellent grappler with the ability to stuff Sonnen’s takedown attempts far better than Michael Bisping did, and Bisping did a great job.
Once that occurred, Sonnen would be in for a long night, one that would likely see Miletich ease the memory of being defeated by a lesser fighter in Matt Lindland by way of giving Sonnen a thumping.
If Sonnen could hit harder and wasn’t so bad at submissions (one of Miletich’s students, Jeremy Horn, has faced Sonnen three times and defeated him all three times via submission) he would probably be a champion by now, but he doesn’t so he’s not.
Still this would be an interesting contest that would pit a very well rounded fighter from yesterday against a very one dimensional fighter of today, and I would have watched every second.
No disrespect intended to the newly inducted member of the UFC’s Hall of Fame, but Tito Ortiz made a career for himself out of calling out fighters either smaller than he was (who can forget his post fight speech after defeating Evan Tanner, where he said he wanted to fight the best, and then proceeded to declare that he wanted to fight a Gracie?) or were many years past their expiration date.
In regards to the latter, he did so against Ken Shamrock on three occasions, and tried to do so again against Mark Coleman.
Given the history between these men, it’s a bout that could have happened in 2001, and it would have been a great one if they could have agreed upon a weight.
Without the normally sizable advantage of youth (at that time Coleman was the Pride FC heavyweight champion, so he hadn’t begun to really suffer the detriments of age), Ortiz would have finally been in against a fighter who was a better wrestler, stronger and incredibly savage.
Ortiz would have held the advantage in reach and submissions, but that’s about it. The rest of the advantages would have belonged to Coleman, which is why Ortiz waited so long before trying to pick a fight with “The Hammer.”
This is one fight that would have been simply brutal for as long as it lasted.
As good as Ortiz was at that time, much of his success was based upon the fact that he knew he was the bigger, heavier, stronger fighter. Against Coleman, that confidence advantage would survive up to the point when Ortiz found himself on his back, being mauled.
Upon learning he was not the stronger man in the cage, nor the better wrestler, odds are he would have continued to fight, but without the same arrogance he normally employed during his title reign.
Ortiz never really suffered a serious beating in his career; yes, he took some hard shots and suffered small cuts here and there, but he never really took a bad beating that saw him seriously bruised and bloodied.
Against a prime Coleman, he would have.
Still, it would have been something to see.
The legend of Brazil vs. the hero of Japan: it’s the kind of headline that sells out stadiums if held in Brazil or Japan.
While Sakuraba was cleaning house in the early days of Pride, taking out one Gracie after another, it was always done before the emotionless eyes of Rickson Gracie, even if he wasn’t in attendance.
It was the fight that should have happened, but never did, for one reason or another. But that doesn’t stop us from dreaming.
No one really knows how great Rickson’s striking game was because he really never had to use it to gain any kind of advantage. His was a ground wizardry and everything he did was to pull the fight into that realm, and once there, the end was certain.
Sakuraba was never a great striker, either. His main goal was to entertain while working for one of his many submissions, all achieved via unorthodox means, and he proved his ground game was rightly recognized as just about the best in the world.
Like Royce Gracie vs. Shinya Aoki, Rickson Gracie vs. Kazushi Sakuraba would only be fulfilling if it took place on the ground, and that’s where it would end up eventually.
Granted, Sakuraba would be able to keep it standing for a while, but national pride—to which Sakuraba is still a joyful slave—would demand he test the legendary Gracie on the ground, and he would oblige.
As they would have never grappled against anyone like each other, there likely would have been a feeling-out period, until Sakuraba would have had enough and went into attack mode, and then we’d get the fireworks we wanted.
I don’t know who’d end up getting burned, but it would be a hell of a show.
Many people may roll their eyes when the see this one and I just don’t care.
Say what you will, but I am a huge fan of both men, and considering that they are in many ways mirror images of themselves, this is a fight I would love to see.
Both men managed to achieve success by developing a ground game that allowed them to be far more than their weakest link: their striking. Both men have striking that could best be described as limited, and thus when facing each other, it is a certainty that they would tie up sooner rather than later.
This would be one of those fights that really educated the fans as to what elite level grappling is really all about.
Both men have highly underrated submission skills, and both are excellent wrestlers who have proven they can score takedowns as needed.
When it comes to pure wrestling, I give the edge of Hughes, and where submissions are concerned, the advantage goes to Shields. However, in both instances, the advantage each man has is very slight.
So where does that leave us?
The answer is twofold: conditioning and power—both belonging to Hughes, with the latter coming by the truck load.
Hughes wins via UD (49-46 on all cards).
So, what really is better: power or skill? Or is it all about technique vs. athleticism?
A lot of talk about a fight between these two men has shown us that there are two sides to the issue: either you believe that Fedor was one of the greatest ever and would burn down Lesnar’s house just like Cain Velasquez did (except worse) or you think Fedor was totally overrated, subsisting on a legend that was built on a steady diet of cans and washouts that never saw him prove himself against the best of his generation.
Come the night of the fight, it would likely be about all of the above, displayed at a fast and furious pace.
Everyone knows what each fighter brings to the table, so it all boils down to who utilizes their strengths better?
Given that Lesnar never liked being hit, and that in order to take Fedor down he would have to pass through that area of space where Emelianenko’s strikes could reach full extension and deliver far more power than anything Velasquez landed, and you’ve got a bloody night for Fedor.
At his prime, Fedor was so incredibly well rounded that many forgot just how cunning he was in the heat of battle. He made it look so easy that everyone dismissed it all as simple greatness or lack of quality opposition.
The truth is Fedor was great because of his mind as well as his body, and he trained himself to take advantage of any opportunity that would allow him to use any of his weapons with devastating effect, be it submissions, brutal ground-and-pound, speed in scrambles and transitions, Terminator-like resiliency or devastating knock-out power.
In short, Fedor really had it all, and Lesnar, as big and strong as he was, and as good a wrestler as he was, wouldn’t have nearly enough to defeat Fedor in his prime.
Fedor via KO in round 2.
Oh but for the damnable distance of time, we could have gotten to see perhaps one of the most entertaining and explosive heavyweight fights ever staged in the UFC: David “Tank” Abbott vs. Roy “Big Country” Nelson.
An epic clash of fists and beer guts, this bout would have ended up with a brutal KO; how else could it end?
Abbott would take one look at Nelson, hate him instantly and then proceed to try and knock his jaw around to the back of his head. Nelson would take one look at Abbott, laugh and make a smart-ass comment and then try to bounce his right hand of Tank’s cannonball like head.
Fights like this one are the reason why beer kegs were invented.
I give the edge to Tank in an all out slugfest, simply because he’s faced guys with “granite” chins before, and if given enough time—and if they were fool enough to keep putting their chin in the way of Abbott’s fists—they ended up out cold.
Odds are, Nelson would continue to suffer a beating until he decided he’d had enough, take Abbott down and submit him in short order.
When Tito Ortiz was in his prime, he looked nearly unbeatable.
He was a huge light heavyweight compared to his peers, and his sheer strength and wrestling game allowed him to bulldoze over opponents, taking them to the ground and pounding them out in short order. He was young, terribly confident and ferocious.
Now, after his retirement, Ortiz is saying that if that younger, prime version of himself would have ever met the current champion in a contest, he would have taken Jones out just like he did everyone else.
Let it never be said that Ortiz isn’t fond of himself or his accomplishments.
But to be fair, we should consider the point: how would a vintage Ortiz have faired against the monster that is Jon Jones?
Ortiz made the most of his size advantage and power, which is what all fighters should do. However, his job was made easier by the fact that the division he ruled didn’t have the same level of athletes that it does now.
In a fight with Jones, the advantages of size and weight would be all but gone, and all that he would have is power. Normally, that counts for a great deal when two fighters of equal skill engage in a contest, but not this time.
Jones would still enjoy a sizable advantage when it comes to reach, and that gives him many advantages over Ortiz, turning the table on the Hall of Famer. Jones could hit him all day at range with his superior striking (and Jones is the superior striker even with no reach advantage), and when the fight became a grappling contest, Jones would enjoy more power not due to true strength but thanks to the power of leverage.
Then, there is another failing of Ortiz: that of a suspect chin. Many of Jones detractors question his chin, but he has never been dropped to his knees by a glancing blow and then actually ran—back fully turned to his opponent—the full length of the octagon to make his escape.
Ortiz has, and that is just one example.
In order to defeat Ortiz, Jones would only need to do one thing: stuff the takedowns, and he could do that all day long, punishing Ortiz from the top position and then on the feet.
This one ends midway through round 3, via TKO due to savage ground-and-pound.
Whenever I see Mauricio “Shogun” Rua fight, I always wonder how he would have done against Bas Rutten, simply because both men love to load up on heavy strikes and then unload their payload, usually with devastating results.
Most people know Shogun by now. He’s still relatively young, but in his Pride-era prime, he was seemingly unstoppable; blowing out opponents via running over them with his explosive striking and Mauy-Thai technique, or submitting them on the ground.
Bas Rutten was another fighter who simply loved to strike, unleashing brutal kicks and straight punches that could put you to sleep if you blinked, and in his prime, standing toe-to-toe with Rutten was widely acknowledged as a bad idea.
Much of Rutten’s striking philosophies are still seen and employed today, although not with as much flair or speed: Rutten could snap out those wicked kicks and you wouldn't know they’d been thrown until you felt them crash into your body. Add to that his belief that being accurate with strikes is just as important as power and you have a very dangerous man, especially when he aims for the liver.
Given that neither of these men would have probably tried to turn this into a wrestling match, we would be treated to a stand-up war that would have been an utter joy to watch.
On the ground, I honestly believe Rua would hold the advantage, although not by much; Rutten ended up having a seriously underrated ground game.
On their feet, this is a coin toss. Who knows?
Much like Shogun and Rutten, a fight between prime Pedro Rizzo and reigning heavyweight champion Junior dos Santos would have been a stand-up war between two great Brazilian strikers who possess different styles and one-strike fight-ending power.
In his glory days, Rizzo was a tactical striker who planned his work and worked his plan when it came to Mauy-Thai. He was at his best when his opponent mistook his boyish looks as a sign of weakness and proceeded to stalk, catching them in bad positions and blasting them with hard kicks to the legs and body and strafing them with punches in bunches.
When his opponent stood still, he was happy to attack with low leg kicks and circle in and out, doing the math before going on the attack. Given that he also possessed a serious chin and had the heart for long, grueling bloody battles, and you have a fighter that is a terror on the feet.
In dos Santos, you have a barnstorming puncher that doesn’t seem to know the meaning of “defense.” Dos Santos is pure offense, and the only times we’ve ever really seen him take a step back is to assess the damage he’s done to an opponent or to simply look for another area to attack.
As a fighter with one-and-done punching power, dos Santos throws combinations more often than not, and can end a fight with uppercuts, hooks and crosses. He also possesses good knees and kicks, although not of the caliber of Rizzo.
A fight between these two men would have been beautiful and ugly all at once. As far as the kicking game goes, Rizzo gets the nod without question. When you look at punches, dos Santos holds the clear advantage.
As always, it boils down to style: the counter-striking prowess of Rizzo vs. the all-in attack of dos Santos.
I see dos Santos winning this fight via KO late in round 4 after both men have taken a hard beating and are bloodied and bruised.
Of all of the fights on this list, this is the one that never fails to get my mind racing.
In many ways, Frank Shamrock was the prototype of the fighter that GSP has become: skilled in many areas, excellent on the ground, relentlessly committed to conditioning, etc.
At the height of his power, Shamrock could do it all: his striking was far better than most (and it was varied), his cardio seemed limitless, his ground game was consistently ranked among the best in the sport, and he always went for the finish. When you add to all of that the fact that he was perhaps the most explosive fighter in the sport, and you have the champion who defeated all comers in the UFC, finishing them all.
GSP is much like this, but he exists as a variation on a theme: he too is dedicated to conditioning, has a good striking game, and like Shamrock is a thinking mans fighter, implementing game plans built to play to his strengths while attacking the weaknesses of his opponents.
The differences between these two greats is found in their ground games: GSP is a fighter who possesses the best wrestling in the division and thus that is the basis for most of his offense, where as Frank Shamrock’s ground game was almost totally based around submissions.
So, who would win between these two men if we would have had the honor of seeing them face each other?
Shamrock enjoys a slight edge in the striking department, but it is very close. GSP is a very good striker, and he has a jab that is far better than Shamrock’s. They are both about dead even when it comes to how they employ leg kicks, save that GSP attacks the outside more than Shamrock, who loves to kick on the inside of an opponents legs, disrupting their balance.
But Shamrock had the better hands overall and he had the better defensive skills on the feet: his head movement was very good and he was a very capable counter puncher, and when he wanted to use his knees, he was devastating.
This is a fight that would only see a true answer to the question via a trilogy.
GSP would have the edge in raw power, takedowns and wrestling, which would see him work tirelessly from the top. Shamrock would have the edge in striking and submissions, constantly moving from the bottom and making GSP work more than anyone else to date and with Shamrocks eye for finishes and his explosiveness, GSP would be in the danger zone at all times, even from the top.
I see GSP winning one fight via a close decision, where as Shamrock wins another via submission.
As for the third fight, who honestly knows? But I would bet the bank that it would win fight of the year, hands down.