I have been reading about his conquests, successes and failures lately and this is a comment I come across often.

I believe that these remarkable people of history are often established to an extent by their birth, such as Alexander's father Phillip having begun to already unify Greece, or Julius Caesar being born to a position where he could join the senate.

Still, some feel that Alexander was lucky in far more regards than most. Perhaps a more intelligent question would be "how lucky was Alexander?"