Timothy was decent at bargaining. Some might even say that he's decent at everything, including planning!
When he started out as a stingray he made some stupid decisions, and that was only natural considering that he had actually been stupid back then, with a low IQ and all, but today, most would consider him the smartest man that they've ever seen! A third-person perspective would help the masses get to the conclusion that he was a genius.
For example, even though the situations he got into got crazier every other day, the main difference in recent events was that he got each situation under his complete control, regardless of the underlying details! Sure he was a polar bear right now, grabbing the head of a huge, angry Frost Orc mamma who might attack him at any minute, but the situation was still under his control. He may seem like a shaman who was trying to heal the wicked, but perspective didn't taint his goals.