Donald vs. Teddy: Dan Responds to Reader Who Thinks Trump Compares to Roosevelt

Donald Trump vs Teddy Roosevelt
Photos: Ronald Riqueros/PMC, iStock

What follows is an editorial submitted by a reader. I thought it worth running, even though I don’t agree with it. My response follows.

by Sidney Baumgarten

I am sure that if Charles Krauthammer were still among us, he would, by now, have compared Teddy Roosevelt (“TR”) and Donald Trump (“The Donald”).

Please forgive me. I am a lifelong Democrat. A few years ago, a good friend presented me with a diorama containing photos of the Rough Riders at San Juan Hill, samples of their medals, and a non-working 45-caliber revolver used by them. It came to me with an inscription that made it obvious I was an admirer of TR.

TR was, for sure, a larger-than-life character, fond of displaying a wide range of knowledge acquired as a voracious reader, Harvard graduate and accomplished classicist. His penchant for the “manly pursuits,” his endearing behavior with children, and his often-bombastic quality made him a president that you either loved or hated. According to the history books, you could not have been neutral about TR.

I have pondered that such a president ended up alongside Washington, Jefferson and Lincoln on the face of Mount Rushmore. While in office, one congressman called him “unreliable, a faker, and humbug.” The editor of a Midwestern newspaper called him “the most dangerous foe of human liberty that has ever set foot on American soil.” None other than Mark Twain called him “clearly insane…and the insanest upon war and its extreme glories.”

TR was also not shy about calling others names: He referred to the critics of his Panama policy as a “small bunch of shrill eunuchs,” tagged the President of Venezuela “an unspeakable villainous little monkey,” and called a U.S. senator “a well-meaning, pin-headed, anarchistic crank.”

It is disappointing that most of the TV pundits have not studied history, political science, or even a bit of classical literature one is supposed to absorb in college, if not high school. Had they done so, or chosen to do some reading now, they would emerge with a somewhat different view of “the Donald.”

One of the most interesting stories of TR is how he was informed of McKinley’s assassination and that he was, at that moment, the new President. He was with his family at their retreat at Mount Marcy (the highest mountain in New York state), deep in the Adirondacks. The Secret Service came from Washington by train to North Creek, then the railhead, took a stagecoach to the foot of Mount Marcy and then horseback up the mountain, where a forest ranger informed TR that he was now the President. Down he came on horseback, onto the stagecoach to North Creek and to Washington to begin his duties as President.

For me, it was confirmation of his love of the rugged Adirondacks and that he was, indeed, the consummate outdoorsman.

The Donald, like TR, is indefatigable. He is a gracious host, certainly caring for his children, and possessed of a clear destiny for our country. You can guess how TR was pilloried for his “gunboat diplomacy,” his “speak softly but carry a big stick” attitude, and his frequent “show of force” to back up his foreign policy. It was, in many ways, more provocative than the Donald’s saber-rattling with Iran and North Korea.

The Donald has endured investigations, accusations, weak-kneed appointees, and downright subterfuge. He has been accused of just about every kind of misdeed one can conjure up. I don’t know how anyone can run the U.S. Government, be Commander in Chief, lead our diplomacy around the world in the face of what he has undergone. And you can rest assured that I would feel no differently if the president was a Democrat.

It is also worthy of note that when TR decided to run for Governor, an affidavit surfaced that he had prepared while he was Assistant Secretary of the Navy. He admitted that he was a legal resident of the District of Columbia, and thus disqualified him as a candidate for Governor of New York. To make matters worse, he had previously declared himself to be a resident of Manhattan to avoid some taxes at Sagamore Hill in Oyster Bay. Can you imagine what MSNBC or CNN would do with that if is was Donald Trump? Impeach! Perjury! And on and on and on.

That crisis ended when the word was spread that TR has done all of that “on advice of counsel!”

On the issue of judgeships, another interesting lesson can be gleaned from TR’s time. Don’t for one minute believe that a “litmus” test for judges really works. TR felt totally betrayed by Taft, his Supreme Court appointee, when Taft ruled against TR’s policies. Dwight Eisenhower often said his two biggest mistakes during his presidency were sitting on the Supreme Court. No matter how many years go by, and who the President may be, there is no way to foretell how any judge will rule on any single case. And so it should be!

What the last two years has revealed is either the vilest hypocrisy in modern times or the sheer ignorance of the media. There are many other historical examples, but looking back at Teddy Roosevelt and watching Donald Trump, there are stark differences and pleasant similarities.

Maybe Mount Rushmore will make room. 


Teddy Roosevelt, at the age of 39, spent a month at Montauk as part of the U.S. Army that had come back from Cuba having overthrown the Spanish dictators there. It was August 1898. Teddy slept in a tent amongst his Rough Riders’ tents. His wife and four of his children visited him there. Wife Edith wrote laughingly to a friend later that Teddy entertained their two young sons in his tent, with the boys sleeping on his cot and he on a table. She and the daughters slept at Third House.

Teddy’s manly pursuits involved wrestling, horseback riding, swimming, hiking and big-game hunting. He was a devoted husband true to his wife by all accounts. By contrast, Trump avoided the draft and has been accused of getting his father to hire a doctor to say he had bone spurs in his feet. He has been married three times, has had affairs, some with porn stars, and was, according to his first wife, Ivana, in her biography, absent when it came to raising his children.

I wonder what Trump would have said to the waiting reporters when he, as a war hero, was arriving at Montauk aboard a troop ship returning from Cuba. Down below decks, many of Teddy’s men were seriously ill with yellow fever, typhoid and other tropical diseases. Teddy leaned over the railing and shouted down the following to the reporters on the dock:

“I am feeling disgracefully well…I feel positively ashamed of my appearance when I see how badly off some of my brave fellows are…Oh, but we had a bully fight.”

My guess is Trump would have leaned down and talked about how he had turned things around and won the day. Amazing what I did, he’d say.

Teddy was a vigorous and beloved man. As far as anyone knows, the only people who hated him were the rich tycoons. Teddy’s efforts resulted in the passing of the 16th Amendment, which permitted taxing the rich. He also was the Police Commissioner of New York City and cleaned out the entrenched corruption during his year in that office. As governor he was planning to do the same, which so terrified the state politicians that they arranged for him to be kicked upstairs. McKinley selected him to be his running mate in the election of 1900. As Vice President, he could do no harm. Teddy became President when a mentally ill person shot McKinley on his visit to Buffalo. As for the Donald, many of the people he surrounds himself with are heading for jail. As for himself, the verdict is yet to be decided.

Both Teddy and the Donald call out their opponents as louts and criminals. Over the years, many have done that. Thomas Jefferson was famous for it. The lies he told about Hamilton are legendary.

Teddy’s “speak softly but carry a big stick” diplomacy brought the United States a new respect. And I think Trump can be credited for doing the same, although with nuclear missiles on the table, it’s a lot scarier.

As for Trump getting his image on Mount Rushmore, I don’t think he’d allow it. Trump is not good about sharing. Better would be his image up top, bigger than the others, and with a big flashing TRUMP nested in his hair.

Trump never has said he admires Teddy Roosevelt. But he’s an admirer of President Andrew Jackson. He has his picture framed on his wall. Jackson is most famous for, one morning, waking up and firing everybody in his cabinet, except one person. That was a fellow Indian fighter who Jackson had made a cabinet member. That man brought a bride into the White House who enraged the wives of the other cabinet members by sleeping with their husbands. When it was suggested by the cabinet that she be banned from official functions, Jackson fired his cabinet. “Loyalty above all” is how he explained it.

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