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I'm a Chinese martial artist, and no fan of Western boxing, so my immediate bias is toward the Little Dragon. But I did used to love watching Ali, back when I was a kid, and he's the only boxer I've ever bothered to watch...he was a showman. More to the point, he was an innovator and an incredibly fast man for one so large. He really was The Greatest.
When you boil it down, power in a strike can come from sheer strength or from speed. Bruce was very fast and he honed his body into pure muscle -- too much so, probably, if you're like me and believe that overtraining may have contributed to his death. Ali is 6'4", right? Regardless, he was taller and very muscular. Reach advantage to Ali's arms, but Bruce's legs (slower than hands, even if you're Bruce Lee, but potentially more powerful) could have neutralized that. Both men were very fast.
Bruce didn't just have expertise at medium range, because his original kung fu style was wing chun, a Southern Chinese system that specializes in infighting. It's likely that Ali would have been at a major disadvantage if Bruce were to get past the zone delineated by Ali's reach or if Bruce were to make contact with his arm or torso (wing chun works heavily on sensitivity training...chi sao 'sticky hands').
One of my kung fu teachers, the one I've thus far spent the most years with, was and is a friend of Ali. What I've heard from him and from another of my teachers is that Ali's style overlapped significantly with the principles common to most Chinese martial systems. He has an appreciation of kung fu, too, just as Bruce did with boxing and fencing.
So who'd win? Either one might prevail in any given match. Both were powerful hitters, because both were quick and strong, but Ali was that much brawnier and larger and that confers advantage, all else being equal. Ali was also a good mover, one of the things that he brought to heavyweight boxing, but Bruce likely had a more fully developed footwork repertoire, combining the bazillions of footwork patterns contained within various Chinese styles with elements from other sources. So Ali was hardly the lumbering behemoth to Bruce's lithe panther, but Bruce probably could have danced at least a few circles around him.
And don't let Bruce's relative physical slightness fool you: he had power in his techniques, power derived both from speed and (to a small degree, at least) sheer muscular power but derived predominantly from linkage. The linking of body parts, the connection through the body and to the ground that generates and delivers power, is all important. That's how the 'inch punch' works and, for that matter, how tai chi is so effective. It's not esoteric BS and handwaving...I'm a large-framed, tall person who has been literally thrown across rooms by tai chi dudes close to half my size. Ditto 'external' kung fu styles...it's all the same.
I don't know how Bruce would have fared if Ali landed a good, solid punch, though. He was not a street brawler (at least, once he left Hong Kong) but he was a big believer in full-contact sparring in his school and even the pads he used didn't diminish the power of committed blows. So he might have survived Ali's fists of fury.
On the other hand, kung fu styles specialize in techniques that are lethal or intended to destroy joints, muscle, eyes, noses, and every other part of the body. It's not just compensating excuses when a Chinese stylist explains a poor showing in a tournament (or refusal to participate in such) on their techniques being "too dangerous" for the ring. They are. Chinese styles are many (MANY many) and diverse, but to a great extent they fall in line with my characterization of kung fu basically being the Chinese art and science of dirty fighting. Tournament rules specifically prohibit most of kung fu's effective techniques. That's certainly the case in tournaments dominated by the martial sport of tae kwon do but even dedicated kung fu tournaments ban the heart and soul of many or most Chinese combat systems...grappling (chin na), for example, is usually verboten. Even those stupid 'Ultimate Fighting Challenge' wankfests, wherein so-called 'martial artists' show utter lack of humility as proof that the American Way trumps Shaolin, have a very skewed playing field (skewed specifically toward Brazilian Ju Jitsu, not surprisingly). A real no-rules match would see an experience Chinese fighter quite possibly ending the match at the outset with a deceptively simple nerve attack. Or with his or her opponent nursing a shattered knee or picking up the pieces of their gonadal units.
Western boxing rules would gut a martial artist's repertoire, that's for sure. Under boxing rules, Bruce probably would have been hammered by Ali. I wouldn't say it was a given, but I'd think it the most likely outcome eight out of ten times. In a rules-free environment, though, it'd be a closer match than most Westerners might expect based on relative sizes of the adversaries. Substitute one of the more advanced kung fu teachers today working in the US for Bruce, one who is very familiar with advanced nerve-attack and smilar techniques, and I'd probably be betting against Ali. That'd probably be true even under boxing rules, because even I know some nerve-jangling techniques that can be hidden within a simple parry or the like (handy for tournaments, actually) and a real master of it could numb your arm (at least) withotu even appearing to do anything. Again, this is not just me buying into the myth but me recounting my own experiences as the numbee.
Look at many Chinese styles and you'll see that Western boxing is basically an integral part of the system -- convergence on effective techniques -- which is not all that surprising if you consider that the Chinese have had 4000 years to work on this stuff. Nothing new under the sun. Boxers can be fearsome opponents -- again, I speak here from bitter experience -- even if you train in a Chinese system that includes essentially the same techniques and tactics: a kung fu dude in a system that has tens or even hundreds of hand and weapons forms or sets is diffusing his or her effort whereas a boxer focuses on just a relative few techniques and trains them to a very high level of performance and power.
Karate systems are the same: they're essentially derived from subsets of southern Chinese styles and do not contain anywhere near the same number or diversity of techniques, but they train those few techniques HARD. Big as I am, I may not be all that likely to get caught by the attack of a goju-ryu karateka because I am more nimble than the average bear, but when they hit me with a basic reverse punch or front kick I am hurting...again, bitter experience, many times over. Scary mofos, some of the harder-core karate types. I have a ton of different techniques at my disposal, and a wealth of strategy and tactics somewhere in my head, along with fast reaction time and some degree of physical and mental sensitivity...my arsenal is far more stocked than that of most karate stylists and certainly of boxers, TKD students, wrestlers (now, those can be some scary folks...even before martial arts I was always a hitter and no good at wrestling) but my side kick is less powerful than that of a TKD dude of similar experience, my reverse punch and front kick are less devastating than a hard-core karate dude of similar experience, and my body remains less supple and relaxed than that of a mid-level tai chi enthusiast. I'm big and fast, like Ali, but I've got more the diverse repertoire of Bruce...in short, either one would thrash me, unless I got really lucky on the day.
Who knows how good Bruce might have become had he not died at 32. I think he probably would have embraced again some of the more traditional kung fu styles, because many are really no more shackled by their traditions than was jeet kune do (ironically, in recent years a property fought over by several of his students). I bet he would have rediscovered tai chi. And Ali is just an icon...he is a great man, in my opinion, warts and all. I hope he sticks around for a while yet, too.
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