Which of these two had been VS. Which of these two was?

Question

My boss and I were having a discussion over a certain point in a line of dialogue, "Which of these two do you think was class valedictorian?" In this case, the dialogue is discussing a specific class which two people (who were referred to in previous parts of the dialogue) were both a part of.

I say this sentence is correct. However, my boss insists that it should be, "Which of these two do you think had been class valedictorian?"

Any clarification would be appreciated!

EDIT: Context was requested in a comment, so I will provide some. The individuals in the line of dialogue were both taking part in a race. Some information is provided about their activities and achievements while in school. The question mentioned above is then posited to the user.

Answer 1

You are overcomplicating the problem. Consider:

• He was valedictorian.
• He had been valedictorian.

The first suggests that we are discussing a particular graduating class; the second, that we are discussing the record of an individual.

"Who was the Lowell valedictorian in 2010?" "Bob was the valedictorian."

"Was Bob doing well in his schooling?" "He had been valedictorian in high-school and then was on the Dean's list in college."

Note that the formal purpose of past-perfect is denoting a completed state, so unless there was some reason to look at the valedictory role as already being in the past at some earlier date, the simple indicative would have worked better. Given that, I would say "was" in most cases.

Answer 2

"Had been" would typically be used when the condition at some point quit being true. In this case, he was the valedictorian. If he lost that title then, for example, he had been the valedictorian until it was discovered he cheated. He lost the title, so had been would be appropriate.