In a reloading scam, a victim is repeatedly approached by con artists, often until "sucked dry". This form of fraud is perpetrated on those more susceptible to pressure after the first losses, perhaps because of hopes to recover money previously invested, perhaps because of inability to say "no" to a con man.
The term has been current at least since 1923, when it was used to describe a specific repetitive stock fraud:

To "reload" a holder of stock, he is approached with an offer to buy from him a larger block of the stock at a higher price than he paid, and about the same time the opportunity is given to him to purchase more at the original offering price. When he has done so, he finds that the bid is an elusive one; it is now for a larger block, and if he buys still more stock in order to take advantage of it, it still keeps ahead of him.The term 'reloading' has since expanded to cover all repeated attempts to scam money from the same victim.
This form is widespread because people who become victims of, for example, a telemarketing fraud, often are placed on a sucker list. Sucker lists, which include names, addresses, phone numbers and other information, are created, bought and sold by some fraudulent telemarketers. They are considered invaluable because dishonest promoters know that consumers who have been tricked once are likely to be tricked again.

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