Assuming God and Jesus are the good guys, I'd say they are incompetent and have no idea what they are doing, and thus is tricked by an inferior opponent. Or they just don't care at all.
However, looking at the situation as a whole, I find it much more likely that if the Judeo-Christian God exists he is the bad one. Why? Because if God is malevolent the world makes a lot more sense right away. You don't have to sit through hours and hours of apologetics for it to kinda, but not really make sense for one. And it would make sense with regards to the Shepard analogy: you protect them until they are ready for slaughter.
Also, the "Love and Fear the Lord" thing is really suspicious. First; why would a loving God want us to fear him in the first place? And why would a loving God try to force people who fear him to love him as themselves? Doesn't seem like anything the God a lot of modern christians try to promote.
Perhaps there IS a such thing as 'enough of enough ... I'm outta here!' -- emotions of exasperation?
Going further back, once upon a time there was Moses, who also was in charge of leading a flock. It was not exactly an inspiring job, considering how many times his flock had rebelled and had to be punished (though it could have been a lot worse had Moses not begged Him to lessen standard divine punitive procedure more than once!) to keep them in line.
Had Christ hung around lot longer, like Moses, I wonder if he would have ended up becoming as exasperated as Moses! Hypertension? Ulcers??
In case of Jesus Christ: He could not have arrived at the worst time. The Roman Empire was at its zenith and local Jewish rulers were, for all practical purposes, vassals to Rome. So ... having his career cut down brutally short might not have been such a bad thing for him.
The reason why I think the Roman Empire was at its zenith at the time of Christ is that the Romans enjoyed political stability under Augustus. However, while the Romans made further territorial gains within two centuries after Christ/Augustus era, they became overextended and could not avoid costly succession struggles.