Lorenzo's uncle,the duke,sets a competition to find Florence's finest painter and cocky Michelangelo taunts Leonardo that he cannot beat him so Machiavelli enlists Lorenzo's help in tricking Michelangelo into painting the duke's least preferred topic,angels and cherubs. Leonardo,however,is annoyed that he is expected to collude in cheating and deliberately erases the smile from the teen-aged version of La Gioconda which he painted using Lisa as his model,thus allowing her, as 'Tomaszo' to win.