Final answer:
James Madison regarded 'liberty and security' as the chief blessings of civil society, with the Constitution's system designed to preserve liberty through justice, influenced by the thoughts of Locke and Montesquieu.
Step-by-step explanation:
According to James Madison, the "chief blessings of civil society" are best described as liberty and security. Madison, a Founding Father and a key architect of the Constitution, believed that government's purpose is to ensure justice, and through its checks and balances, preserve liberty. His viewpoint aligns with that of John Locke and Montesquieu, who both influenced Madison's political theory. Locke emphasized the transition from a state of nature to a civil society as a means to protect one's property and thus gain the protection of laws, an impartial judiciary, and the enforcement of laws.
Montesquieu championed the idea that liberty involves having the protection of laws while maintaining maximum freedom and autonomy, suggesting that laws should primarily promote public safety. The Bill of Rights, a forefront protector of civil liberties in the U.S. Constitution, further illustrates the importance the Founders placed on liberties such as freedom of speech and the right to be secure in one's possessions.