I thought you were going to challenge me. It is obviously Kurt Engle. OK, Seriously…this a broad question. There are countless considerations, such as, the most skilled, or the most successful in competition. Likewise it could be the one who developed the most revolutionary techniques, or the one who has had the greatest influence on grappling. By these standards, I’m inclined to nominate Rickson Gracie, qualified by his undefeated record in four hundred plus fights. I might also nominate Helio Gracie for his influence on contemporary grappling. Through careful deliberation I have not chosen Rickson or Helio despite their obvious qualifications.
Linguistic dissection of the question affords me considerable latitude in my choice. Obviously the superlative “greatest” is meant to be applied to “grapple” plus the inflection “-er,” or one who grapples, but it does not explicitly indicate that this individual must be greatest at grappling. Considering this convenient oversight, I choose to read this question: Who is the greatest person who grapples or has ever grappled? With that in mind, I cannot think of a better choice than Theodore Roosevelt. Not only is he a bad ass, but a great American. He was surely the greatest man I know of who was also a grappler. Argue amongst yourselves if you must, but for me the matter is certainly decided. Below is an excerpt from a letter he sent to his son.
In addition to training as a weightlifter, boxer, wrestler, fencer, and (of course) shooter, Roosevelt was a student of judo/jiujitsu. He lined the White House recreation room with mats to train in jiujitsu, creating what may have been the first Western dojo.
From a letter to son Kermit, dated 02/24/1905:
Yesterday afternoon we had Professor Yamashita up here to wrestle with Grant. It was very interesting, but of course jiu jitsu and our wrestling are so far apart that it is difficult to make any comparison between them. Wrestling is simply a sport with rules almost as conventional as those of tennis, while jiu jitsu is really meant for practice in killing or disabling our adversary. In consequence, Grant did not know what to do except to put Yamashita on his back, and Yamashita was perfectly content to be on his back. Inside of a minute Yamashita had choked Grant, and inside of two minutes more he got an elbow hold on him that would have enabled him to break his arm; so that there is no question but that he could have put Grant out. So far this made it evident that the jiu jitsu man could handle the ordinary wrestler. But Grant, in the actual wrestling and throwing was about as good as the Japanese, and he was so much stronger that he evidently hurt and wore out the Japanese. With a little practice in the art I am sure that one of our big wrestlers or boxers, simply because of his greatly superior strength, would be able to kill any of those Japanese, who though very good men for their inches and pounds are altogether too small to hold their own against big, powerful, quick men who are well trained.
From “Theodore Roosevelt’s Letters to His Children” edited by Joseph Bishop.
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