If it's before 2001 this might be possible, but after 2001 there is a great deal more cooperation between governments - he won't be able to get on a plane with one passport and off with another one, and if he's a US citizen he would be making it extremely difficult for himself to be entering the US on any other passport.
I know of people here in the US who have three citizenships, at least one with a country that forces them to renounce it, and they've never had any problem concealing this. AFAIK they just travel to the appropriate countries with the appropriate passports and it's not an issue
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