Friday Fun

About two months ago, President Donald Trump made news when the first UFC fight was hosted on White House grounds. Over 125 years earlier, President Theodore Roosevelt was making news by participating in martial arts matches at the White House himself.

While Roosevelt engaged in several types—boxing, jiu-jitsu, and wrestling—he particularly liked boxing. As he wrote in his Autobiography, “I regard boxing, whether professional or amateur, as a first-class sport . . .”

Since we get asked every so often about Roosevelt and boxing and in light of the aforementioned contemporary connection, we figured it was high time that we wrote a Substack post about it. So, without further ado, we present Theodore Roosevelt the boxer.

Roosevelt first learned how to box after a group of boys made “life miserable” for Roosevelt while he was on a stagecoach ride to Moosehead Lake in Maine, as he recalled in his Autobiography.

And his first few years boxing weren’t easy. According to Roosevelt, “I was a painfully slow and awkward pupil, and certainly worked two or three years before I made any perceptible improvement whatever.”

His boxing master before college was John Long, “an ex-prize fighter” who occasionally held competitions, including one in which Roosevelt won the lightweight contest. In his Autobiography, Roosevelt called it “the only one of my exceedingly rare athletic triumphs which would be worth relating.”

When he got to Harvard, Roosevelt continued to box, although he noted in his Autobiography he “never attained to the first rank” even at his own weight.

According to an article in The Harvard Graduates’ Magazine in December 1901, “The only occasion when he ever entered a public match was in the Spring of his Junior year. Roosevelt defeated William W. Coolidge but lost in the championship bout to Charles Stedman Hanks, as reported in this March 1879 newspaper article in the Boston Globe.

In fact, it was this match that Roosevelt wrote about in a lengthy February 1909 letter to Thornton H. Simmons when the latter inquired if Roosevelt had been a lightweight boxing champion at Harvard and if so, what year.

As Roosevelt explained, the matter had come up a few years prior, and he had researched and discovered he had not been a lightweight champion at Harvard.

After college, Roosevelt continued to box, noting in his Autobiography, “When obliged to live in cities, I for a long time found that boxing and wrestling enabled me to get a good deal of exercise in condensed and attractive form.”

One of the men Roosevelt boxed with—Michael “Mike” Joseph Donovan—even wrote an autobiography entitled The Roosevelt I Knew: Ten Years of Boxing with the President—And Other Memories of Famous Fighting Men.

In it Donovan described Roosevelt “the fighter” in great detail, including his “first fistic encounter” with him when Roosevelt was governor of New York. Donovan noted that when Roosevelt left to change, he was a governor. When he returned, he was a fighter. His boxing outfit was a sleeveless flannel shirt, his Rough Rider khaki uniform trousers, and “light canvas shoes without heels.”

This was the first of many fights between Donovan and Roosevelt throughout his political career. In late 1904, Roosevelt invited him to visit the White House and box with him. When Donovan replied to accept Roosevelt’s invitation, he informed Roosevelt that he had contacted his glove maker to make two sets for Roosevelt.

When Roosevelt replied on November 19, 1904, he told Donovan to wait before coming to the White House since he wanted to “get Congress fairly going before I begin the boxing.” After that, he looked forward to Donovan coming down with gloves and putting “them on with the President in the White House!”

Initially, Roosevelt had hoped for Donovan to come in early December but had to delay his visit after Roosevelt wrenched his thigh and broke a blood vessel in one eye while sparring and playing singlestick with Ted and some young army officers. But Roosevelt still wanted Donovan to come, “I want to have you in the White House and put on the gloves with you myself, and see Ted do so.”

Even though Roosevelt told Donovan to come, he worried about whether or not he could keep boxing, writing to Kermit, “I am rather reluctantly coming to the conclusion that boxing, like wrestling, is somewhat too violent a sport for me. I have been trying it with Ted and his fellow football player, Church, as well as Roly Fortesque, and Dan Moore, and wrenched my thigh again.”

However, his concerns didn’t seem to last too long, as Roosevelt had quite an energetic fight when Donovan finally made it to the White House. As Joseph Bucklin Bishop wrote in a January 1905 letter to Roosevelt, “I heard a piece of news yesterday which I suspect will give you as deep, if not deeper, joy than you experienced on the night of the Election.”

One of Bishop’s friend’s sons received boxing lessons from Donovan and also knew Donovan’s son. Apparently, Donovan’s son called Roosevelt “a pretty hard hitter.” Bishop thought that would give Roosevelt joy, but he also cautioned him to go easier on Donovan “for you may have a dead pugilist on your hands presently if you are not careful,” he warned.

Donovan continued to box with Roosevelt in the White House, including the night before Roosevelt’s second inauguration between five and six in the evening, as Donovan mentioned in his autobiography.

Boxing had become a habit for Roosevelt, as it was around this time in 1905 that Roosevelt wrote to Kermit “I box three afternoons a week.” (Time management expert Laura Vanderkam considers three times a week a habit, so she would consider Roosevelt’s boxing a habit.)

In addition to Donovan, Roosevelt boxed with all kinds of people, including his cousin, Roly Fortescue, as he related in a February 1905 letter to Kermit that he didn’t want to box with him because he was afraid of hurting him: “[A]nd I did, giving him a most gorgeous pair of black eyes.”

Roosevelt also mentioned in a January 19, 1905 letter to Kermit, he permitted a new wrestler in the White House named simply “Grant.” He told Kermit that two days prior to his letter, he “bloodied Grant’s nose,” which bothered Roosevelt since he thought Grant wasn’t hitting him hard although the president requested him to do so.

Roosevelt’s sons also took up boxing, which delighted him. Ted had taken up boxing around the beginning of 1905, although a doctor later told him to stop after he broke his nose “again boxing.”

And Kermit took up boxing in 1907 when he was eighteen years old. As Roosevelt wrote in a November 7, 1907 letter to Kermit, “I am glad you are going to take up boxing. It is certainly a fine thing to know. I learned to box with great difficulty; but it was most useful to me when I did know how to defend myself.”

As for Roosevelt, his boxing days waned after Colonel Daniel T. Moore, his military aide—called only “a captain of artillery” in his Autobiography—hit his left eye during a bout, leaving Roosevelt almost totally blind in that eye. We believe it may have been in December 1904 when Roosevelt wrote to Donovan about breaking a blood vessel in one eye (mentioned above).

According to Moore, he didn’t learn he blinded Roosevelt for close to a decade until Roosevelt’s injury became public news in late 1917 after Roosevelt told some journalists about it.

Newspapers across the country jumped on the story and featured articles like “How Colonel Roosevelt Lost His Eye” that detailed the accident and the science behind it (see below).

But for those who had read Roosevelt’s Autobiography, which came out in 1913, they would have already known since he mentioned the incident in it. As Roosevelt explained in his Autobiography describing the injury, he decided to “acknowledge that I had become an elderly man” and traded boxing for jiu-jitsu. (See this letter where he compares wrestling and jiu-jitsu.)

But Roosevelt wasn’t completely done boxing, as there are multiple examples of him boxing after late 1904 in the digital library—even as he was insisting that he was “too old” for boxing!

For example, in February 1909, Roosevelt sent his friend, Leonard Wood, a letter of introduction to William Sikamith, with whom Roosevelt notes he “has been doing a little boxing.” Roosevelt especially enjoyed his “system of physical exercise” and hoped Wood would as well.

Moreover, Wood wasn’t the only person Roosevelt reached out to about Sikamith. He also asked Commissioner Henry Litchfield West to look into incorporating the regimen, including boxing, into schools in Washington, DC.

However, it does seem to be true that Roosevelt boxed less after the incident with Moore although that didn’t stop the press from depicting Roosevelt as a boxer in political cartoons. We included just two examples from 1907 below, although there are plenty of others in the digital library.

Even as he boxed less, Roosevelt continued to support the sport, brushing aside common concerns about ruthlessness in boxing that had started to become more prominent in the 1910s. As Roosevelt wrote in a 1915 letter to E.E. Keevin, his views of boxing remained the same as he had written in his Autobiography.

We’ll close with correcting an error we’ve seen related to Roosevelt and boxing. It is sometimes stated that Roosevelt boxed wearing glasses, but that is inaccurate. In fact, the error goes back to a December 1901 article written by Curtis Guild, a fellow Harvard graduate, about Roosevelt at Harvard published in The Harvard Graduates’ Magazine: “He sparred with a pair of large glasses literally lashed to his head.”

Guild even suggested that Roosevelt’s glasses were the reason Hanks bested him in the championship bout in 1879: “As Hanks good naturedly said himself, a lucky blow of his that knocked off Roosevelt’s glasses settled the matter.” Only it wasn’t true. If you read the 1879 newspaper article we mentioned above about the match carefully, nothing is mentioned about glasses.

Moreover, Roosevelt himself wrote to Guild after the article was published correcting the error: “I liked that article very much, but just let me say one thing! You are a fencer and so you naturally forget about boxing. I did not wear glasses while I sparred – could not have. My great difficulty came from the resulting nearsightedness.”

But the image of Roosevelt boxing in glasses was too compelling and soon became a part of public memory. Another friend from Harvard, Charles G. Washburn, even added it in an original draft of his biography about Roosevelt.

When Washburn passed along a copy to Roosevelt for review in 1916, Roosevelt praised Washburn for the biography but noted the error about him boxing in glasses: “Curtis Guild used to say this and quite a number of people firmly believed that they saw me so box. . . . Now, Charlie, no human being could box with spectacles or glasses on. It would be absolutely certain that he would have them broken in the first minute or two and in all human probability he would then be blinded permanently.”

Washburn took Roosevelt’s correction to heart, removing the offending information and adding several sentences from Roosevelt’s 1916 letter about not boxing in glasses in the published version of his biography, Theodore Roosevelt: The Logic of His Career.

With that, we’ll throw in the towel and conclude this deep dive about Roosevelt and boxing with two sentences from Washburn: “He was fond of athletics, but never greatly excelled; he never claimed to: he did the best he could. Boxing was his favorite sport . . .”

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