Why does John pretend to be homeless?

To secretly test his long-lost grandson Jay's character and loyalty.

What happens to Anne after the truth emerges?

She is jailed for embezzlement once Jay's heir status is revealed.

The Homeless Billionaire Grandpa

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The Homeless Billionaire Grandpa — A billionaire disguises himself as a vagrant to secretly assess his long-lost grandson, who suffers cruelty from his mercenary spouse.

John, a wealthy patriarch, vanishes into street life to observe Jay, a grandson he never knew. Jay exists trapped in a gilded cage, tormented daily by his wife Anne and her predatory relatives who drain his resources and dignity. Despite the humiliation, Jay shields the ragged elder he befriends, offering protection even after Anne's infidelity casts him out penniless. The deception shatters when John reveals Jay as the appointed head of a billion-dollar European division. Anne faces prison for embezzlement while Jay gravitates toward Sophia, his sharp assistant.

Quick answers

Why does John pretend to be homeless?: To secretly test his long-lost grandson Jay's character and loyalty.
What happens to Anne after the truth emerges?: She is jailed for embezzlement once Jay's heir status is revealed.