“My definition of a free society is a society where it is safe to be unpopular.”

"To Practice Thrift and Oppose Embezzlement (1952)
1950's

Source: Democracy in America, Volume I (1835), Chapter X-XIV, Chapter XII.

Collected Works,Vol. 10, pp. 44–49.
Collected Works

The scope and nature of the constitutional guarantee of the freedom of the press are to be viewed and applied in that light.
New York Times (November 28, 1954).
Judicial opinions

“The Contradiction in Objectivism,” 1968

1880s, Speech on the Anniversary of Emancipation (1886)
Context: I admit the charge, but deny that nature, race, or color has anything to do with the fact. Any other race, with the same antecedents and the same conditions, would show a similar thieving propensity. The American people have this lesson to learn, that where justice is denied, where poverty is enforced, where ignorance prevails, and where any one class is made to feel that society is an organized conspiracy to oppress, rob, and degrade them, neither persons nor property would be safe... While I hold now, as I held years ago, that the South is the natural home of the colored race, and that there must the destiny of that race be mainly worked out, I still believe that means can be and ought to be adopted, to assist in the emigration of such of their number as may wish to change their residence to parts of the country, where their civil and political rights are better protected than at present they can be at the South... The Republican party is not perfect; it is cautious even to the point of timidity; but it is the best friend we have.

Interview on Middle East Television Network, February 18, 2004 http://georgewbush-whitehouse.archives.gov/news/releases/2004/02/20040218-10.html
2000s, 2004

Source: "The Failure of Nonviolence" (2013) https://theanarchistlibrary.org/library/peter-gelderloos-the-failure-of-nonviolence, Chapter 2. Recuperation is How We Lose

Source: Motivation and Personality (1954), p. 17.
Context: For our chronically and extremely hungry man, Utopia can be defined simply as a place where there is plenty of food. He tends to think that, if only he is guaranteed food for the rest of his life, he will be perfectly happy and will never want anything more. Life itself tends to be defined in terms of eating. Freedom, love, community feeling, respect, philosophy, may all be waved aside as fripperies that are useless since they fail to fill the stomach. Such a man may fairly be said to live by bread alone. It cannot possibly be denied that such things are true, but their generality can be denied. Emergency conditions are, almost by definition, rare in the normally functioning peaceful society.