Original: The citizens expelled it in 1552, allying with France: this was unacceptable for Charles, who sent his general Gian Giacomo Medici to lay siege to it with a Florentine-Imperial army.
Simplified: This citizen expelled it in 1552, with France: this was unacceptable for Charles, who sent his general Gian Giacomo Medici to lay siege to it with a Florentine-Imperial army.