In his essay on civil disobedience, Henry David Thoreau criticizes Webster for being a politician, whose experience is only as part of the government. This makes him both short-sighted and committed to prudence rather than to wisdom. Thoreau is politely grateful for what Webster has done—compared to others: “his are almost the only sensible and valuable words, and we thank Heaven for him.” He praises him as the so-called “Defender of the Constitution” but says this defensive position makes him “not a leader, but a follower.”

The harshest criticisms that Thoreau applies to Webster relate to slavery. He quotes from Webster’s writings about the Constitution, states’ rights, and slavery:

Still thinking of the sanction which the Constitution gives to slavery, he says, “Because it was part of the original compact,—let it stand.”

Thoreau sees this as a position based in “merely political relations” rather than originating from one’s own moral convictions. Webster endorses the idea that slave-holding states are authorized by the Constitution to regulate as their constituents prefer.

Thoreau brings up the New Testament in relationship to the kind of laws might be written but have not yet been put in place—if any legislator were sufficiently wise and practical “to avail himself of the light which it sheds on the science of legislation." In the society he envisions as truly ”free and enlightened,” the state would:

recognize the individual as a higher and independent power, from which all its own power and authority are derived, and treats him accordingly.

The issue of sovereignty is crucial here in reference to the “neighbor,” by which Thoreau refers to his opposition to the US invasion of Mexico.