Gideon was an awesome general. He overcame overwhelming odds with almost nothing. It wasn't his excellent leadership that did it, it was his faith. It was proof of his commitment to God that he won with so few numbers. Because it was only through God a victory could have been eeked out with only 300 men vs the tens of thousands against them.

At least his men didn't fleece them, well, there was some fleecing that happened, like several times, just to be sure that it was a go. Gideon didn't want to do anything without making sure it really was God speaking to him. Testing God wasn't such a great thing to do but it worked out for Gideon. I'm sure he saw at least one and was confident, but it took 3 proofs from God to give him the confidence to do what was wanted of him.