I was in the room in 1985 during the US/Iran/Israel negotiations that eventually led to Iran-Contra, and while I had no authority to make commitments for the American government, I had plenty of opportunity to ask questions and talk at length with the others. It was not a happy experience, and it was worsened by the knowledge that, while we spoke, a top American CIA officer was being tortured to death by the Iranians.
Hostage negotiations between a Western democracy and a hostile totalitarian regime lopsidedly favor the evil regime. Its leaders do not care about human life, while ours are often driven by concern over the fate of their citizens. You can see that in the case of Israel, which releases hundreds of terrorists for a single Israeli hostage, and you can see it in those US/Iran/Israel negotiations back in ’85: President Reagan was very passionate about saving our hostages, as Israeli prime ministers, including Begin and Netanyahu, have been about saving theirs.
Our leaders have long claimed that we don’t pay for the release of hostages, nor do we negotiate with terrorists. False on both counts. Indeed, I don’t know of any democratic country that doesn’t do both. To stay with Iran, President Carter negotiated a deal for the release of the diplomats from our Tehran Embassy–the deal entailed the release of Iranian funds blocked in US banks–and Reagan’s several deals with the Iranians sent weapons to the mullahs. More recently, Obama’s negotiations with Iran have also included American hostages in Iranian jails, as we know from the fact that he raised that question with Iranian President Rouhani during their phone conversation last September.