Ken Jennings himself did that for the express reason of throwing off his opponents. As the category selector he would have an extra couple seconds to start thinking in that direction. Totally fair game for Watson to do too.
I agree that Watson started with a higher value clue in order to look for the Daily Double. Statistically the fourth row has the highest concentration of them. DDs are valuable not just because of the opportunity to double up or bet more than the clue's actual value, but also because you get exclusive access to the question without buzzer competition.
As for Watson's early lead, that happened because the clues chosen early happened to be the types of questions it could answer quickly and reliably. Computers are great at stuff like 4-letter words and searching Beatles song lyrics. Computers are less great at clues where the hint drives the answer, like the one about "don't name Voldemort" or the "Final" category where the hint is in the category name. It just so happened that those harder clues for Watson came after the easier clues.
When Ken jumped into a category, notice that he started at the highest values.
Also because doing that searches for Daily Doubles, which are concentrated at the higher value clues.
I noticed the same thing, but I really hoped it was unintentional. It doesn't feel like it's a fair fight otherwise, since it means he's exploiting a weakness intrinsic to his competitors. The whole point of this competition is to show that a computer can compete and win at a human level. If it weren't, then why force him to physically push a button to ring in? If Watson is intentionally jumping categories to confuse humans, then it sort of feels like he's cheating a bit.
As I write this, I realize a lot of this comment is motivated by my bruised human ego, but it just doesn't feel quite right to me.
If it helps your bruised human ego, another human player could attempt to exploit this exact same weakness.
(I don't know if Watson is programmed to do this or if it is an actual weakness of human players.)
Late in the first round you can see Jennings change his strategy a bit -- he starts ringing in before he knows the answer. Jennings is exploiting the fact that Watson won't ring in until it has confidence in an answer.