Lo que nos sorprendió fue su cortesía, como si nunca nos hubiera menospreciado.

Questions & Answers about Lo que nos sorprendió fue su cortesía, como si nunca nos hubiera menospreciado.

Why do we use the past perfect subjunctive (hubiera menospreciado) here?
The phrase como si (as if) always triggers a past subjunctive form because it introduces a hypothetical or contrary-to-fact situation. Since the hypothetical event—him looking down on us—happened before the time he surprised us, we use the past perfect subjunctive (meaning "had looked down").
Why does the sentence start with Lo que instead of just Qué?
Qué with an accent means "what" in questions (like ¿Qué es eso?) or exclamations. When you want to say "what" in a statement to mean "the thing that" or "that which", you must use the neuter relative pronoun lo que.
We see nos twice in this sentence. Are they doing the exact same job?
They both translate to "us", but grammatically they are slightly different. In nos sorprendió, nos is an indirect object (the courtesy was surprising to us). In nos hubiera menospreciado, it acts as a direct object because he was directly undervaluing or looking down on us.
Could I use hubiese menospreciado instead of hubiera menospreciado?
Yes, absolutely. The past subjunctive always has two valid endings: the -ra form (hubiera) and the -se form (hubiese). In Latin America, you will hear the -ra form much more often in everyday speech, but both are perfectly correct and mean the exact same thing.
What is the literal breakdown of the verb menospreciado?
It comes from the verb menospreciar, which is a combination of menos (less) and preciar (to value or prize). It literally translates to "to value less", which is why it is used to mean "to underestimate", "to look down on", or "to despise".

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