How did (riverine) toll castles operate?
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There are two issues at work here, economics and power.
The first is economics. Yes, in theory, it was possible for merchants to use alternate routes or take evasive actions, but in practice, this was impractical. The tolls were typically a small fraction of the value of the cargo, collected many times. The cost of the evasive action would be a much higher fraction of the cargo. (Tolls were typically set at less than the cost of the nearest alternative.) Most people would rather pay a smaller, rather than larger fraction of the same.
The second is power. A warlord who could afford to build a castle was a very rich and powerful person indeed. Having built the castle, it was a simple matter to construct a "toll booth." Most merchants (other than e.g. Jacob Fugger), were less powerful than most castle owners.
Who would likely win in a showdown? Basically only a sovereign entity had greater power than the average castle keeper. Or a quasi-sovereign person (Fugger was the official lender to the Holy Roman Emperor, which made him the "J.P. Morgan" of his time and place.)
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Source: stackoverflow.com
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