That was Kettle Hill, part of the San Juan Heights. The Regulars attacked the other hill, San Juan and has a much tougher time. They took that eventually as well.
Donald Trump got 5 deferments to military service, the last for bone spurs. He said his Vietnam was fighting VD.
To compare them is laughable. Roosevelt had a life of public service including the military before the presidency. Trump had a life of bankruptcy, reality TV, snd screwing over small businesses before he got there. Only you would try to compare them.