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> Israel had the year of Jubilee, where every 50 years debts would be forgiven

How would this work? Wouldn't people just not enter into contracts near that 50 year mark? Is it randomized?

If everyone knew that debt resets were to happen, the contracts in the 49th year would likely be only for small things.

That probably also means that for larger purchases, more cash up-front is required the closer it is to the Jubilee year.

It did end up having that effect, which is why Hillel the Elder created a device called the "Prozbul" which transferred debt to the court before the Jubilee year, thus preventing forgiveness and enabling borrowers to borrow even close to the Jubilee. This is one of the few (maybe only) true loopholes invented by the Rabbis, with the justification "so as not to close the door to borrowers."

Edit: Wikipedia link https://en.wikipedia.org/wiki/Prozbul

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