Remember the old SAS adage : ‘He who dares, wins.’
Although in the case of your DD fleet commander, I think he dared and lost… ;)
The comments though are valid, if you want a commander to do what you want, stick to orders and not tangle with the big boys, then go for one who is cautious or extremely cautious. If you want a maverick who may well go bouncing around like a loose 4.7” on deck, then go for an aggressive or extremely aggressive. They can never be trusted to do the predictable thing (which can be either an asset or a liability, depending on if it works)…
I’ve had in the past flotilla’s of half a dozen PT boats shaping up to a Japanese armada lead by the Yamato that is trying to tiptoe past my flimsy picket line to do a sneak bombardment of Munda or Tulagi. My PT boats got pulverised to matchwood, but it sure did make a mess of his surprise attack (used up most of his ammo trying blowing my PT boats to kingdom come…, I had four flotillas there each of c. half a dozen that he had to fight his way passed before he even got within bombardment range).
On the subject of aggression, it is interesting to note that, despite the Bushido code and Samurai spirit of most of the Japanese soldiers and airmen, their commanders were surprisingly timid. Nagumo’s over-caution threw away their advantages at the Battle of Midway (hindsight is a wonderful thing…) and the IJN also threw in the towel at the Battles of the Coral Sea and also Eastern Solomons, handing draws to the USN when in reality the IJN should have pushed home and finished off the suffering American carrier groups (at Coral Sea they let the Yorktown escape, and at Eastern Solomons they let the Enterprise off the hook). It could also be convincingly argued that at the final great battle, that of Leyte Gulf, the Japanese Commander’s nerve broke when he was within one card of finishing off the US Escort Carrier Group that he was pulverising.
Perhaps the best most glaring example of this was at the first battle of Savo island (early hours 08.08.42) when the Japanese admiral (can’t remember his name, think it began with an ‘M’) brilliantly surprised and outfought not one but two Aussie-American cruiser groups, leaving four heavy cruisers either sunk or sinking and the rest of the surface units severely damaged, then decided to withdraw with the Guadalcanal invasion transports and supply boats at his mercy. Had he decided to carry on, plunge in and either sink or else disperse them, then unquestionably the Guadalcanal campaign, and arguably the entire Pacific one, would have taken a completely different turn…