STUMPERS: The Hardest SSAT Verbal Question

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STUMPERS: The Hardest SSAT Verbal Question

The analogy questions on the SSAT are one of the most challenging portions of the test, especially for first-time test takers. To perform well on the analogies section, students must not only be adept at identifying  relationships between concepts, but also must have a solid mastery of above-grade-level vocabulary.

The Test Innovators platform gathers and provides data on how many students answer each question correctly, and we were curious to see which SSAT Upper Level verbal question stumped the greatest percentage of students.

Before we break down the question, let’s see if you can answer it correctly: 

Vagabond is to itinerant as

If you chose Answer A, you are in an elite group! Only 9.1% of students selected this correct answer–far below the expected value of 20% for a question on which all students randomly guessed an answer.

This question hinges mostly on knowledge of some very advanced words and the nuances of how they are used. Let’s analyze it. .

The first word of the given couplet, vagabond, is fairly uncommon in 21st-century American English. Students who know the word might envision a medieval wanderer or Great Depression-era job-seeker. Some students may be familiar with the related word vagrant and know that it refers to a person, often suffering poverty, who travels from place to place in search of a living. The second half of the couplet, itinerant, is the defining characteristic of a vagabond—it describes unsettledness or a tendency to wander or travel. Astute students will recognize the similarity between this word and the word itinerary, which is the plan for a journey. So, a vagabond is itinerant, and we’re now looking for an answer choice where the second word is a defining characteristic of the first. Only knowing these words, though, can potentially lead us down the wrong path.

Answer D, with 30.2% of guesses, received the plurality of student responses, and it’s not hard to see why this answer choice is so tempting. Both words seem highly related to the given couplet–they evoke an image of voyages and journeys. However, the word pioneering is not quite right here. Pioneering describes a first: an invention that no one has thought of before; a step into uncharted territory. Someone who takes a trip to London could be described as a traveler, but they would not be described as a pioneer; millions have already made the trip to London. 

*Note:  If traveler were replaced with explorer, this would have been a sufficient answer.

Even if you can eliminate answer choice D, you are still in for a challenge. We can eliminate choice C because its second word, practitioner, is a noun, not an adjective like itinerant (which is a word that actually does sound like it could be a noun, but isn’t). Choice E doesn’t really make any sense: congenial (meaning harmonious or friendly) doesn’t at all describe a rebuttal.

Choice B is another toughie, though, even if you know what the words mean. A faction could potentially be described as partisan (strongly biased or one-minded) but it is not necessarily so—whereas a vagabond is undoubtedly  itinerant.

If we are able to eliminate these wrong answer choices, we’re left with choice A: autocrat is to despotic. These are difficult  words. A student who is moderately well-versed in Greek roots will probably recognize the two parts autocrat is composed of. Auto– relates to the self (as in autonomy, autobiography, autograph, etc.), and –crat refers to government or rule (bureaucrat, aristocrat, democrat, etc.). An autocrat by definition rules by themself and has absolute power. The second word, despotic, is harder. There are not any recognizable roots, and a student will need to know what a despot is in order to figure out the definition. This word may have come up in history class a few times; Joseph Stalin, Benito Mussolini, Mao Zedong, and Adolf Hitler are all examples of despots. Despotic is the adjective that describes a despot (a ruler with absolute power and authority), and despot is a good synonym of autocrat. Therefore, vagabond is to itinerant as autocrat is to despotic.

Preparing for the ISEE? Check out our piece on the hardest ISEE verbal question.

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Originally published on November 15, 2017. Updated on January 30, 2026. 

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