For the benefit of people who doesn't watch wrestling, do you mind explaining why the WSJ would support an administration at the end of its term and was likely to lose? Or for that matter, why "major publications" like the new york times have no problem with making anti-incumbent endorsements[1], despite the claim that "The WSJ and other major publications have a vested interest in brokering access by tailoring their coverage to be friendly to those in power"? Whatever you said about "heels" sounds like a "heads I win, tails you loose" sort of proposition, where you can excuse any sort of counter-evidence as part of a greater ruse or whatever, making your theory basically unfalsifiable.
A simple translation on the transactional relationship: because they know who butters their bread, and they know they can waffle into the next administration or current thing as long as they stay in the general good graces of the intelligence apparatus. It's wet behind the ears view a major news agency as anything other than an extension of the intelligence apparatus. Whatever supposed political leaning is symbolic and minuscule in the overall influence of direction and probably tied to useful wetness of ear of the hosts ego and not the overall apparatus. The heel comment could be likened to a hammer and anvil, with one party playing each role and the roles alternate over time but an overarching direction is being achieved by higher level thinkers.
[1] https://en.wikipedia.org/wiki/List_of_United_States_presiden...