https://www.history.com/this-day-in-history/theodore-rooseve...
I guess your definition and mine are incompatible. The forensic evidence is quite clear: https://en.wikipedia.org/w/index.php?title=File:Political_ad...
I also agree that it's crucial to critically examine historical figures and not idealize them blindly, it's also essential to avoid oversimplifying or misrepresenting their lives.
Theodore Roosevelt certainly had privileges, but it would be unfair to dismiss his contributions and experiences entirely. The challenges he faced and his contributions to American history, both domestically and internationally, are more complex than a single perspective or narrative. Dismissing an entire life based on a few events can be as misleading as uncritical adulation.
I am all for being critical of class-based inequalities but having resources does not exempt one from adversity. Very few people would consider someone who spent their whole childhood in debilitating sickness, someone who lost their wife and mother 2 days apart, rode western with cowboys through a winter in North Dakota as someone LARPing in controlled environments. Not all of this is romantic ideology. One can be born with a silver spoon and still experience the realities of life, the trauma of losing loved ones, prolonged sickness, etc. Saying that he "never faced any actual adversity" is black and white while being arguably wrong.
The Edmund Morris trilogy gives a good overview of his life for those interested.
WP says the battle was over a ridge with a couple major peaks, and that the highest was indeed cleared and occupied by other soldiers the day before, but the following day Roosevelt’s troops (among others) did face real resistance taking the other major peak. It reads like the first day was rather more intense, but the second wasn’t exactly a cake-walk, and it definitely doesn’t read like they just walked up to an already-taken position.
Yeah, he was also a rich guy born with a silver spoon, who never faced any actual adversity in life, and so spent his time fetishizing those who do, while LARPing as one of them in controlled environments.
Read into his whole trip through South America; it's an absolute disgrace. The attitude you illustrated above led to the death of his guide (and almost his son) and him having to be hauled out of the jungle by natives on a stretcher for weeks.
Even the charge up San Juan hill is pure mythology. The enemy position had already been cleared by the 10th cavalry, and he brought up the rear. The guy is a complete work of fiction as he is taught to school children these days.