Someone recently posted this, which got me wondering:
"Mark Twain on Teddy Roosevelt:
“[Roosevelt] is naively indifferent to the restraints of duty and even unaware of them; ready to kick the Constitution into the back yard whenever it gets in the way; and whenever he smells a vote, not only is he willing but eager to buy it, give extravagant rates for it and pay the bill not out of his own pocket or the party’s, but out of the nations, by cold pillage.” (February 16, 1905)
“Roosevelt is the whole argument for and against, in his own person. He represents what the American gentleman ought not to be, and does it as clearly, intelligibly, and exhaustively as he represents what the American gentleman is. We are by long odds the most ill-mannered nation, civilized or savage, that exists on the planet to-day, and our President stands for us like a colossal monument visible from all the ends of the earth.” (April 3, 1906)"
What is the context behind these criticisms?
I have a book called, Mark Twain and The Colonel, it's been a while since I read it, but basically it boils down to Roosevelt's violent nature. Roosevelt was one of those rare macho men who felt that war was actually good for the soul, (Imagine that) Twain on the other hand, felt that the US did Gods work when they liberated Cuba from Spain, but did the opposite with the Philippines, because they wouldn't let a local government take over after it was liberated, essentially making the Philippine a US colony. As I said, it's been awhile since I read it, and I remember the book not really giving me all the information I had hoped for, but it might be just what you're looking for.
https://www.amazon.com/Mark-Twain-Colonel-Theodore-Roosevelt/dp/1442212276/ref=nodl_