I think Timur would certainly be in the discussion, he was supposedly a very avid chess player and the Tamerlane chess variant is attributed to him.

Emperor Justinian I of the Roman (Byzantine) Empire. The man has it all, skill, shrewdness, patience, and the ability to think strategically on multiple levels. With apologies to Trajan, Justinian might just have been the real "Last Roman." Hi dynasty was one of the last to be named in Latin. His dynasty was also the last one to rule Rome itself.

Justinian spent his entire career getting amazing things done with never quite enough resources to do them properly. He weathered the plague and invasions from literally all sides, locked horns with a Persian empire at the height of its own strength, and still managed to reclaim several lost Roman provinces including Hispania, Italia and Africa. He goes down in history as one of the greatest individual monarchs the world has ever known.

It’s an impossible question to answer. There are some truly fantastic generals that we know about, and all had some chance at defeating any of the others under the right conditions. Flat out, Napoleon had the most recorded victories of any known General, and in his prime he was certainly a contender for top spot, but he never had to fight the Golden Horde, possibly the only pre-modern army faster than him. He had Marshalls under him that would also qualify as top of the line generals in their own right. Archduke Charles, one of the only men to defeat Napoleon while Napoleon was at in his prime, would also have to be on the list. Then there is the great Korean general Eulji Mundeok, a man capable of directing hundreds of thousands of men while fighting terrible odds and coming out on top, or Emperor Tokugawa, who had one of the most elite medieval armies in the word, or any one of a dozen ancient and classical era Chinese generals…

Cardinal Richelieu or Axel Oxenstierna? I would look for people who were able to see moves in advance and design a plan. Along this theme would be some of the Native American leaders who were able to keep their people afloat despite the advantages colonizers had, when one thinks about how few Iroquois there were, yet how long they resisted colonial powers, that has to be some higher level strategy. Certain African leaders would also be nominees as well.