Conversation so far:
When was Leonardo da Vinci born?
Leonardo da Vinci was born April 14/15 1452.
What year was Leonardo da Vinci born?
Leonardo da Vinci was born 1452.
What time was Leonardo da Vinci born?
In what town was Leonardo da Vinci born?
Leonardo da Vinci was born in the Tuscan hill town of Vinci.
What village was Leonardo da Vinci born in?
Leonardo da Vinci was born in the Tuscan hill town of Vinci, in the lower valley of the Arno river in the territory of the Medici-ruled Republic of Florence.
What area was Leonardo da Vinci born in?
Leonardo da Vinci was born in the Tuscan hill town of Vinci, in the lower valley of the Arno river in the territory of the Medici-ruled Republic of Florence.

Question: What was his biggest shame
Self-contained rewrite: What was Leonardo da Vinci's biggest shame?