Being robbed made Holden cry, when the elevator guy (Maurice, the pimp) and the prostitute (Sunny) took 5 dollars from his wallet and Maurice punches Holden in the stomach. (This happens in Chapter 14, on page 103, at the top of the page).
Also, Phoebe giving Holden her money that she planned to buy Christmas presents with ($2), because he told her he was broke, made Holden cry. (This happens in Chapter 23, on pages 178 to 179).
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