It's not so much he is trying to lose, he is a very weak fighter and has no idea how to. It's like he is living in a dream world and dealing with ethical people. And his selection of the asses around him seem to be the height of stupidity.
His political ‘brain trust’ comes from Massachusetts politics: they have no understanding of American political sentiment nationwide and particularly misunderstand independent voters in swing states. Yet, they are confident that because they are from MA they understand moderate and independent voters better than anyone else.
Applying a Massachusetts political mentality nationwide is a certain losing approach.
(And as to Saul, what are they doing with a 30yo twit as their spokesperson for a presidential candidate anyway?)