Was he a United States Senator?
Was he Secretary of State or Secretary of War?
- No, he was not a businessman/captain of industry.
- Yes, he was a United States Senator.
- That’s really two questions, but no, he was not either Secretary of State or Secretary of War.
for 18, I was looking tyring to narrow it down to the most “prominent” (IMO) cabinet postions. Acutally i was thinking was going to be Robert Todd Lincoln, but that is obviously wrong now.
I’ll take a guess
John Sherman
which upon edit is also wrong because he was Secretary of State. so it is not a guess.
Off the record, El: would you consider a career in the judiciary to be separate from his political career?
No, it’s not John Sherman. Although I really should count that as a guess. 
His career, for the guy I’m thinking of? Or such a career generally? Perhaps you should rephrase.
In the U.S. Senate, did he represent a state generally considered to be Midwestern?
- Yes
Such a career generally. Sorry- no elegant way to phrase that.
Off the record, El: would you consider a career in the judiciary to be separate from his political career?
Perhaps this is more elegant:
Off the record, El: would you consider a career in the judiciary to be separate from a political career?
Not necessarily.
- Was he a Supreme Court Justice?
- Yes!
Since no one has guessed his name, I think I win. You may keep guessing to determine the individual, if you like.
Aha! Salmon P. Chase, our most delicious Senator, SC Justice and Secretary of the Treasury.
- Yes. And the first to call himself “Chief Justice of the United States,” and not just “of the Supreme Court.” All of his successors have done likewise, and now it’s codified at 28 U.S.C. 1.
RNATB, would you like to start our next round?
Sure. I’m thinking of a person.
- Male?
- Now alive?
Yes, no.
- American?
- Fictional?
- Yes
- Yes!