To put one’s hand in one’s pocket. To give money (generally to some charity).
Put your pride in your pocket. Lay your pride aside for the nonce.
To be in pocket. To be a gainer by some transaction.
To be out of pocket. To be a loser by some transaction.
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Entry taken from Dictionary of Phrase and Fable, edited by the Rev. E. Cobham Brewer, LL.D. and revised in 1895.