Might mean (unverified): Complainer who frequently expresses dissatisfaction.
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We found one dictionary that defines the word whining Willy:

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  1. whining willy: Wiktionary

Definitions from Wiktionary (whining willy)

noun:  (derogatory, informal) Someone who whines incessantly; a whiner.
noun:  Alternative letter-case form of whining Willy [(derogatory, informal) Someone who whines incessantly; a whiner.]

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