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As a DM I think it is a poor idea to fix character build issues by throwing extra gear at them. I do not reward failure. I certainly do not reward failure more than success.
"Let him learn his lesson on his own" comes across as harsh but it is close to the concept I go with. I would not drop extra loot only one character could use in excess of what other characters have. This breeds jealousy among players. It is likely they would be concerned why one player is getting more loot than another and plead favoritism.
I would rather the game unfold naturally and if he discovers that his build has left him wanting to offer to help him. Perhaps along the way you could point out where some of his weak spots are if he has them and offer advice.
In the end, it really is the player's choice how they build their character. Right? I mean, it isn't like you are going to tell him he isn't allowed to build his character any certain way, are you? So what is the real question here, anyway?