It was attempted recently in the news, and has been attempted many times in the past, but has it ever worked when attempted in the U.S.?
If you include prisoner swaps with foreign countries under your interpretation of hostage takings, then those have certainly happened. The best-known example is probably the 1960 exchange of Francis Powers (the pilot of the U-2 that was shot down over the Soviet Union) for Rudolf Abel. Here is a more recent example (from 2019).
I am not.
What I’m talking about is a straight, all done in the U.S., “Let my brother/friend/leader out of prison, or I’ll shoot this pregnant nun!!” type of situation.
My guess is that if this ever happened, it was probably back in the old west. I could picture someone like Jesse James pulling off this sort of thing.
I doubt it’s ever been pulled off. No jailer is going to release a prisoner without some sort of legal document telling them to. A judge or parole board has to give a “legal” opinion about why a prisoner must be released. Your best bet is getting a governor to grant a pardon, but good luck finding a politician that cares more about a pregnant nun than their career.
It’s not entirely far-fetched that this could happen; in 1975, West Germany released five imprisoned members of a left-wing terror group in exchange for a politician taken hostage. It was a high-level political decision taken at cabinet level. I know the OP asked for US cases, but I’m mentioning this to illustrate that it might not be limited to Wild West scenarios.
But I think it should be noted in fairness that the German government soon regretted their decision when the terrorists tried to pull the same trick again, and then came the Landshut plane hijacking, the GSG-9 (German SWAT forces) intervention in Mogadischu, the kidnapping and murder of Hanns Martin Schleyer, and the suicide in prison of the terrorists that the kidnappers wanted to free. Some people still claim that it was not suicide but murder (link in German), which is improbable, but the discussion alone shows how much the German state regretted ever making a deal with terrorists and what the sentiment among many, perhaps even the majority of Germns was at the time: no negotiations, no quarter.
Another incident related to Germany. In October 1972, Lufthansa flight 615 was taken and the hijackers demanded the release of the three surviving terrorists from the Munich Olympics the month before. The West German government acceded to their demands. There have been allegations that the government was complicit in the hijacking as a way to avoid the security burden of keeping the men, and to avoid future terrorism related to the Israeli/Palestinian conflict.
Are there any incidents that happened in the U.S.?
It appears to still happen fairly often, at least when the hostage-takers are foreign states and/or foreign operatives (though, in the case of foreign states, the American “hostages” are usually more properly classified as “prisoners”). A couple of recent examples:
In 2014, the U.S. exchanged five members of Al Qaeda, who were imprisoned at Guantanamo, to the Taliban in exchange for captured U.S. Army private Bowe Bergdahl.
Also in 2014, the U.S. exchanged three Cubans, who had been convicted and imprisoned in the U.S. on espionage charges, in exchange for American government contractor Alan Gross, who had been imprisoned in Cuba, also on espionage charges.
But, the sort of hostage-taker and immediate, local situation like last weekend’s situation at the synagogue in Texas? I’m having a hard time finding any sort of recent examples in the U.S.
And this is precisely the type I am looking for.