Roosevelt's Judo experience
Roosevelt trained judo under two instructors (John O'Brien, and Yoshiaki Yamashita) for a period of around a few months each in 1902 and 1904. He maintained an interest in the art after this, corresponding and reading on it, and may have continued to sporadically train with wrestling partners, but by his own autobiography's account he only trained for a few years at most:
Accordingly I thought it better to acknowledge that I had become an elderly man and would have to stop boxing. I then took up jiu-jitsu for a year or two.
No contemporary records indicate he was awarded any grade during this time, and as such the oft-quoted brown belt remark appears to be a later invention, possibly based off of seemingly speculative newspaper remarks of the time e.g.
There are seven degrees in jiu-jitsu. The President's instructions are proficient in five degrees and Mr. Roosevelt Intends to have all five of them.
The earliest reference to any belt/grade conferred to Roosevelt appears to be from 1966:
Yamashita did not create a rage for judo there, but he did have some prominent pupils, including Teddy Roosevelt. The president practised three times a week and qualified for a brown belt.
However, the USJA in 2007 posthumously awarded Roosevelt an honorary 8th dan grade for his contribution to introducing the art to America:
The United States Judo Association (USJA) posthumously presented 26th President Theodore Roosevelt with an honorary black belt for embracing the sport of Judo at a special ceremony at Sagamore Hill in Cove Neck on Saturday, November 17th. TR admired judo’s ability to build character, promote confidence and teach fair play and sportsmanship.
1902: Training under O'Brien
Jan 3, 1902: Roosevelt's interest first sparked by a letter from William Sturgis Bigelow, in which he described jiu-jitsu and provided him with the contact details of John J. O'Brien.
Feb, 1902: O'brien suggests a course of 8 weeks.
Mar, 1902: Roosevelt writes to O'Brien inviting him to instruct him.
Mar 1902: Roosevelt begins lessons with O'Brien.0
c. May, 1902: Roosevelt ceases lessons with O'Brien.1 2
It appears O'Brien taught Roosevelt in hour long lessons 1 or more times a week:
The second Sunday that I was in Washington when I was giving the President his lesson between 9 + 10 a.m...
1904: Training under Yamashita
Dec 3, 1903: Roosevelt is introduced to Yamashita and Kawaguchi.9
c. 1904: Roosevelt begins lessons with Yamashita:3 4 5
Feb 2, 1904: Bigelow sends Roosevelt a book on jiu jitsu from Tokyo.5
April 26, 1904: Roosevelt discusses his lessons with Yamashita to Secretary of State, John Hay.10
c. May, 1904: Roosevelt ceases lessons with Yamashita5 6
1905 - 1906: Roosevelt's opinions on Judo
c. 1905: Roosevelt instigates judo training at the US Naval Academy in Annapolis, taught by Yamashita.
Feb 24, 1905: Yamashita is invited to the White House for an exhibition match, Roosevelt makes some remarks on the difference between Judo and American style Wrestling, and the role of strength in combat:
Yesterday afternoon we had Professor Yamashita up here to wrestle with Grant. It was very interesting, but of course jiu jitsu end 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 jiujitsu is really meant for practice in killing or disabling your 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
throw 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 as well trained.
Feb 17, 1906:
I am not satisfied about the giving up of the judo or jujitsu at the Naval Academy. It is not physical exercise so much as it is an extraordinarily successful means of self-defense and training in dexterity and decision. Naturally, elderly men of a routine habit of mind who have known nothing whatever of it are against it; but I know enough of boxing, wrestling, rough-and-tumble fighting, and of the very art in question to be absolutely certain that it is of real and on occasions may be of great use to any man whose duties are such as a naval officer's may at any time become. I should like to have it continued next year at the Naval Academy.
Letter to Bonaparte, February 17, 1906
Mar 3, 1906: Bonaparte, in a memorandum of March 3, 1906, to the Bureau of Navigation, ordered judo to be continued at Annapolis.
May 4, 1906: Yamashita rehired, judo taught for 6 months at the Naval Academy.
Aug 15, 1906: Bigelow sends Roosevelt 6 uwagi (上着) (judo jackets), suggesting family disputes may be resolved by a bit of weekly judo.7
Further Reading: Professor Yamashita Goes to Washington (1998)