President Grover Cleveland is pictured on the most recently issued $1,000 bills, first printed as a small Federal Reserve Note in 1928. Prior to 1928, Alexander Hamilton was featured on notes of the same denomination beginning in 1918.
The $1,000 note was officially discontinued in 1934 and was slowly withdrawn from circulation beginning in 1969. As of May 30, 2009, just 165,372 $1,000 bills were known to exist. The Huffington Post reports that in 2013, a $1,000 bill was auctioned off in Illinois for $2.5 million. The price paid for the bill set a world record for a U.S. banknote sold at auction.