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Reader question: In this sentence – Hillary’s supporters had the deepest pockets – what does “deepest pockets” mean? My comments: Hilary Clinton? If so, this means that people who supported Hillary Clinton were rich and wealthy, well, richer and wealthier than, say, those who voted for Barack Obama. At least that would probably make sense during the two’s rivalry in their challenge for the Democratic nomination for President during the last US election. Anyways, deepest pockets refer to the richest and most resourceful people, who, in this case, referred to people who voted for Hillary or had the most money in funding Hillary’s run for office. Deep pocket equals to wealth? Yes. You see, in the old days, before the advent of paper checks and credit cards, and especially among those who didn’t even have wallets, people carry their money around in their pockets. And if you had a lot of money on you, you needed to have a large pocket to contain them. And if it was large, it was deep – presumably you had to dig deep in order to reach the bottom pile of notes and coins. Well, I do not suggest pocketful of coins alone but you get the picture. The bigger and deeper the pocket, the more cash it carries. Hence the saying that, metaphorically speaking, he who has a deep pocket has the wherewithal, the money and means to do something. | 
