Cleveland portrait, n. — Green’s Dictionary of Slang

Cleveland portrait n.

[the head of US President Grover Cleveland (1837–1908), which is printed on the bill]

(US) a $1,000 bill.

1952

(con. 1920s) ‘Harry Grey’ Hoods (1953) 147: ‘How much?’ [...] ‘A couple of those Cleveland portraits should do it.’ Max peeled off two one-thousand-dollar bills.