All-Green
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Some of the points to ponder over before considering who the best Military Commander is :
1) Where were the battles fought? (Home or Away)
2) What was the posture? (Offensive or Defensive)
3) Was there any number advantage?
4) Was there any technological advantage?
5) Was there any tactical advantage?
When I see generals in the light of above mentioned points only 3 leaders stand out:
1) Alexander The Great
2) Julius Caesar
3) Napolean Bonaparte
Khalid bin Waleed consistently led an understrength Army to victory after victory against the two superpowers of his time, Roman Empire and Persian Empire which had superiority in numbers and technology.
The fact that he is a general of Islam usually lets his accomplishments go unnoticed, however purely on military merit he was one of the most complete commanders ever to have fought.
Be it higher strategy of conducting an entire war, in field tactical grasp of a battle or personal courage and skill of arms, this man was peerless in all the battles he fought against the best armies of his time.
To me Khalid and Alexander are the most complete and accomplished Military commanders since they were warrior generals and not only were master strategists and tacticians but extremely daring and great warriors, it is nearly impossible for a man to have all these traits.
I guess this feat cannot be repeated anymore because we are now in the age of guns, missiles and modern communications
Commanders will not lead the front lines and inspire their troops with feat of arms.