Handicap

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Whenever two men wanted to barter possessions of unequal values, they played a game known as “hand-in-cap”, in Medieval England. They would find an umpire for their game. All the three men put a small token amount in the cap.
The umpire would decide which of the two exchanged articles was of less value and how much money must be added to it to make the offer fair.
The two persons would put their hands in their pockets. If both of them drew out money from their pockets, they agree for the barter and the exchange takes place.
If only one person drew put money, only he agrees for the exchange. So he gets the forfeit money and no exchange takes place.
If none of the two took out money, the deal was abandoned. The umpire took the forfeited money.
By the 17th century, ‘hand in cap’ was used in racing to decide which horse should carry extra weight to make the race fair.
Later the word came to denote anything which acts to one’s disadvantage.