In terms of actual planning, intelligence and actually carrying his/her objective
Shan Yu. The guy did everything right.
I still call BS on the mountain scene. How could a girl in Han dynasty China, who likely rarely left her village, let alone climb a mountain, know how avalanches work?
And after losing all those men, he still got the emperor right where he wanted him, in the middle of a huge celebration surrounded by his followers and guards too.
Probably his only flaw was losing sight of his objective towards the end and going for revenge instead of killing Shang and securing the emperor, though that in itself isn't inherently bad since it's more like just getting sidetracked, not deterred completely.
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