#29: Grover Cleveland
Est. Net Worth: $33 million
Cleveland was a self-made man who rose from modest beginnings in upstate New York. He worked as a lawyer and later served as sheriff, mayor, and governor. Known for honesty and integrity, he saved much of his earnings and invested wisely, setting himself up for life after politics.

When he left the presidency, Cleveland returned to private law practice and made smart financial decisions. He lived comfortably in Princeton, New Jersey, until his death in 1908. Though not extravagantly rich, his prudent management left him well-off for his time.
