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.