1900's - TR
1910's - Wilhelm II
1920's - Henry Ford
1930's - Adolf Hitler
1940's - Winston Churchill
1950's - Ike Eisenhower
1960's - Lyndon Johnson
1970's - tie; Richard Nixon & Ruhollah Khomeini
1980's - tie; John Paul II & Ronald Reagan (Gorbachev was a reaction to them, not a tone setter)
1990's - tie; Saddam Hussein, Newt Gingrich, Tony Blair, Slobodan Milošević
2000's - Osama Bin Laden (though if you ask me again in a few years, I might change my mind
Hilariously contradictory. Not that that's a bad thing.
Not really, Churchill defined the problem of Nazism long before others even recognized it, and he did the same thing with communism.
Gorby wasn't a leader in any true sense of the word. He was picked because the people were starting to demand perestroika, he merely granted them what they wanted. When the Soviet Union was collapsing, he did everything he could to try to hold it together, and failed. He wasn't opposed to communism. He did what he did because he hoped that, by loosening the restrictions of the old order, he could preserve it, because people would naturally see what was "good" about communism and disassociate it from the "bad". He wasn't prepared to accept the notion that communism was inherently bad, which was the conclusion that most Russian people had already reached. He only gets credit for anything because he is falsely perceived as a "peaceful" figure, as opposed to Reagan, who was a "terrible warmonger".
Gorbachev was (in part) reacting, but he was reacting to a lot more than just Reagan. If Reagan influenced the end of the Cold War (and he probably did), it is generally recognized; but that he was standing on the shoulders of metaphorical giants is only more dimly sensed.