I think the person that's being described is Henry Hudson. He took several trips out to sea and successfully made it to the New World on his third one. I think New York was also called New Amsterdam under the Dutch, but I'm not certain.
The would be Dwight Eisenhower. After graduating from West Point in 1915, Eisenhower served as a lieutenant. Although he didn't see any combat in WWI, he trained tank corps in Pennsylvania as a lieutenant colonel in the Army. He is more famously remembered for serving as a five-star general and the Supreme Commander of the Allied forces in the European theater during WWII.
Portugal created trade forts along the coast rather than inland because their goal was to control trade routes. They were not looking to build and control a land empire. They were after the route needed to gain access to the East Indies, India, and China. All they needed to control was the coastal area.
