Naïve, callow. “Otherwise” suggests that Gottlieb did not find Steinbeck’s political views admirable. “Adolescent disaffection” suggests that he found Steinbeck’s views in some sense immature, so let’s look for negative words that mean something like “immature.” Naïve and callow are the best options. Perspicacious and keen both suggest insight, nearly opposite of what we’ve anticipated. Contemptible is negative, but with no suggestion of immaturity—make sure to use the clues provided without adding your own ideas. (Note that naïve is sometimes written with two dots over the “i,” as in the original French, and sometimes without.)

Flagitious, heinous. First, we read that in the view of the commanding British officer, Adams and Hancock had committed “offenses,” so we might anticipate a word like “offensive.” Second, they were the only rebels whom he would not pardon or forgive, so he considered their behavior “unpardonable, unforgivable.” If we put these all together we’ll get something like “unforgivably offensive.” Both flagitious and heinous match this meaning. Boorish means something like “crude,” but is much too weak a word to fit this sentence.

Disingenuous, artful. We want a word that means “not as naïve as one pretends.” Disingenuous mean precisely that, and one meaning of artful is “deceptive.” This sentence is difficult because the word impressed is used to refer to making an impression in a negative way. Finally, culpable means “guilty” and is an attractive trap, but goes further than the clues in the sentence allow us. The clues clearly indicate that we need words that mean “not naïve.”

Specious, spurious. If Machiavelli only “pretended” to endorse the claims to power, and if they were subject to exposure and caricature, they must have been not only illegitimate but ridiculous. None of the answers suggests ridiculousness, but two answers—specious and spurious—mean the claims are false. While not synonyms, both words describe claims that are superficially attractive, but in fact false.

Champion, proponent. The second half of this sentence (after the semicolon) tells us that Chris Anderson charges money for his products, and is introduced by an ironic “interesting.” This makes it likely that he supports the idea of information being free. Champion and proponent both imply support (detractor and critic are a pair with the opposite meaning of what we want).

An impasse, a stalemate. If neither side of the debate is willing to give an inch to the other, then it would be impossible for a solution to be found. So the debate is more or less frozen. Both a confrontation and an engagement imply some kind of clash, but the sentence implies that any kind of serious clashing is now over (“no one had anything new to offer”). An impasse and a stalemate reflect the static nature of the conflict.

Ramshackle, dilapidated. The key to this question is the phrase “tolerated presence,” which indicates that the “abodes,” or houses, are different from the “opulent estates.” The pivot phrase “aside from” also provides a nice clue.

Ramshackle and dilapidated, which both mean “run-down,” are best. Archaic, meaning “old” or “old-fashioned,” is close, but doesn’t possess the same connotations of disrepair or neglect that the two correct answers do.

Myriad, plethora. The virus spread to a large number (a myriad, a plethora) of bird species. Watch out for trap answer surplus, which means “an excess” and would not be appropriate to describe bird species.

Curtailing, undermining. By “obviating,” or “getting around,” the traditional channels of legislation, the government is making formal dissent impossible. In other words, it is curtailing or undermining such dissent—words which both mean to “prevent” or “undercut.”

Teeming, abounding. This terrible battle seems to have killed everything (“razed,” “eerie stillness”). In contrast, the streets and squares were once full of or bustling with (that is, teeming or abounding with) life.