trash = To beat up; assault.
The word is not usually used for physical attacks against people. If a rock band trashed a
hotel room, they have left it filthy, littered with liquor bottles and used condoms, and perhaps with some damage, requiring extra work from the staff. If an industrial spy trashed your
home, he was looking for blueprints, research papers, letters, etc., that his employer could use to compete with your company; he pulled all the clothes our of your drawers, scattered your food and dishes all over the kitchen floor, and opened up your medicine bottles and got the pills all mixed up; he may have made holes in the walls looking for hidden compartments, pulled your plants out of their pots to see if anything was hidden under them, even dug up your lawn and garden. If a journalist trashed a politician's
reputation, she dug up things from his past that he didn't want people to know about--like Romney's humiliation of a gay student at his school when he was young, or Obama's fraternization with a Christian minister who held racist opinions.
We also use the term "trash-talk," which is a less serious version of trashing. To trash-talk someone simply means to insult him, either to his face or to other people; the insults may not even be true.
outright disdain = despise very much
"Outright" means obvious and straightforward, not surreptitious. To say that America has outright disdain for the financial industry is to say that we do not trust its people or its institutions--not at all, and we're not bashful about saying so.
fatter cats = rich people?
A fat cat is a cat who is pampered by his owners, getting lots of extra food. Metaphorically, a fat cat is a person who is regarded as pampered by society or its leaders; specifically someone who is very wealthy and powerful, usually because of an inheritance or illicit business dealings rather than through honest hard work. The term is used most commonly for people of this type who can be counted on to contribute to a political campaign, in order to promote a candidate who will feel indebted to them, and craft laws that will help them become even wealthier and more powerful. The fatter cats are simply the fat cats who are even fatter than the regular fat cats; i.e. more wealth, privilege and influence.
"these Chicago guys" = why Chicago? Not W.D.C?
[We don't abbreviate "Washington, District of Columbia" as "W.D.C." It's "Washington DC." It took me a minute to figure out what you meant. And we leave out the "DC" as long as it's clear that we don't mean the state of Washington, whose most well-known city is Seattle.] I'm not sure why they chose Chicago because I'm not familiar with the subject of the article. They may be referring to Chicago because that's where Obama started his political career, so the guys there still help him. Or it could be a reference to Chicago's notoriety as the American center of organized crime, led by the famous gangster Al Capone in the 1920s. Obama is an outsider to Washington, without a strong network of allies here, so I wouldn't expect a journalist to write about strong support from "Washington guys." Jimmy Carter had the same problem when he was president, and it did him in. So did Ronald Reagan, but he overcame it. So did Richard Nixon, and in his attempt to overcome it, he ruined his career and his life.
op-ed = a newspaper page, usually opposite the editorial page, that features signed articles expressing personal viewpoints.
It's simply an abbreviation of "
opinions and
editorials." These days, the editorials and opinions are usually mixed. The difference is that the opinions are signed as the work of a single writer, whereas the editorials are not signed, and presented as the judgments of the newspaper itself and its executives.
campaign literature -- mom-and-pop shops -- executive washrooms -- guillotine-bound French royalty I just don't understand.
Campaign literature is literature prepared by the candidate's campaign staff and distributed to the voters to attempt to convince them to vote for him or her. In many U.S. states the citizens themselves are allowed to propose new laws (or to repeal existing laws), so there are also campaigns for and against these laws, and there is campaign literature for them too.
A
mom-and-pop business is a small one that is run by a family, with most or all of the workers also being family members or at least very close friends. Small family businesses are regarded with affection and nostalgia. They are contrasted with corporations, which are regarded as soulless and indifferent to the welfare of the citizenry.
An
executive washroom is the private bathroom/restroom/toilet/W.C./whatever-you-call-it attached to the office of an executive. It is for his personal use only, not available to the employees, and usually has luxuries and elegant fixtures that the employee restrooms don't have, for example, a bidet or cloth towels. An executive restroom (we don't usually call them "washrooms" in the USA; they're "bathrooms" at home and "restrooms" in public places) may also be simply the communal restroom on the upper floor of an office building where all the executives have their offices. They share it with each other but not with the general employees, and it may still have luxuries and elegant fixtures.
To suggest putting campaign literature into mom-and-pop stores (we don't usually call them "shops" in America, that's British English; although we use the term in some specific cases such as a "pet shop" or a "doughnut shop") rather than into executive bathrooms is to suggest that the campaign should be directed at the common folk, not the aristocrats.
Guillotine-bound French royalty--I enjoyed that one.

During the French Revolution many members of the ruling family were not simply thrown out of office, but executed. The guillotine had recently been invented so it was often used for this purpose. In fact the guillotine is associated with France and specifically with the revolution. To suggest that a group of wealthy aristocrats are "guillotine-bound," i.e. "bound for execution," means you think that their days of power will soon be over and they will not be simply removed from power but punished severely, if not actually executed. Again, the writer is saying that these are not the voters that the candidate needs to appeal to.
his soundest campaign strategy yet why use "yet" here? I seldom see yet following may in a sentence.
One of the many meanings of the word
yet is "until now, so far, heretofore, to date, up to this moment." So the writer suggests that this may be the most sensible strategy the candidate has devised up until now. He may come up with something better tomorrow. In other words, the writer thinks that there's no point in Obama trying to appeal to the wealthy capitalists because he believes they won't vote for him under any circumstances. He seems to feel that Romney is one of the guillotine-bound aristocrats too, so they'll all vote for him.
If you go to see the new James Bond film later this year, you might walk out of the theater saying, "This is the best Bond movie yet."
I sang Celine Dion's "The Power of Love" at karaoke last week, and my friends said it was my best song yet.