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Douglas Harper's Etymology Dictionary
simoleon

slang for "a dollar," 1895, American English, of unknown origin. Related sambolio is attested from 1886; perhaps this was altered based on Napoleon, name of a late 19c. French gold coin.

Wiktionary
simoleon

n. (context US slang English) One dollar.

Usage examples of "simoleon".

Which is pretty sleepy until the next week, when my brother's agency announces the big Simoleons Sweepstakes.

It's the same deal with Simoleons -- everything gets reported to the government.

Here are the simoleons, as our young friend, Comrade Maloney, would call them.

Now it so happens that an uncle of mine some years ago left me a considerable number of simoleons, and though I shall not be legally entitled actually to close in on the opulence for a matter of nine months or so, I anticipated that my father would have no objection to staking me to the necessary amount on the security of my little bit of money.