See this excerpt from the Taibbi-Chomsky conversation:
Chomsky: We were a “City on a hill.”
Taibbi: Exactly.
Chomsky: Did you ever go into the origin of city on a hill?
Taibbi: No, I didn’t.
Chomsky: It’s an interesting case. The term had never really been, barely been used before Reagan. But Reagan picked it up, and did the “Shining city upon a hill” speech.
But if you go back and you read John Winthrop’s sermon, he says almost the opposite. When he says we’re a city on a hill, what he means is everyone is looking at us, and if we don’t live up to the ideals that we profess, we’re going to be punished.*** Of course, in his case, by the Lord. Not by society.
So it’s really saying we’re exposed, we have to try to live up to these ideals. He didn’t say we were doing it, by any means. In fact, he knew we weren’t. That was the point.
Taibbi: Instead, they turn it into a catch phrase for exceptionalism.
Chomsky: Yeah. So wonderful, isn’t it?
Taibbi: Hilarious.
This is the footnote, too:
*** From Winthrop’s sermon: “For we must consider that we shall be as a city upon a hill. The eyes of all people are upon us. So that if we shall deal falsely with our God in this work we have undertaken, and so cause Him to withdraw His present help from us, we shall be made a story and a by-word through the world. We shall open the mouths of enemies to speak evil of the ways of God, and all professors for God’s sake. We shall shame the faces of many of God’s worthy servants, and cause their prayers to be turned into curses upon us till we be consumed out of the good land whither we are going.”
I'm skeptical as to whether Chomsky is correct about this, but it's really hard for me to interpret the text. I mean, what Chomsky says doesn't seem to be a correct interpretation to me, but I'm in no position to judge because I have zero historical expertise as to the historical context. Plus, I find it hard to even understand such an old-fashioned text. I did find this discussion, though, which lays out some ideas about the original meaning of the phrase.
The expression itself was most likely inspired by the passage from the Sermon on the Mount, and specifically by the Parable of Salt and Light (Matthew 5:14-16), that in King James' Version John Winthrop was most likely familiar with has been rendered as follows:
- Ye are the light of the world. A city that is set on an hill cannot be hid.
But the idea of the city or a kingdom on top of the hill that would welcome all the worthy people is far older than the New Testament, as in the Book of Isaiah (Is 2:2) we can find the following passage:
And it shall come to pass in the last days, that the mountain of the Lord's house shall be established in the top of the mountains, and shall be exalted above the hills; and all nations shall flow unto it.
In the light of the original Winthrop's sermon, Chomsky's remark that the 'city on a hill' is an example for both the outsiders and the inhabitants but only if the city dwellers follow their ideals is correct, but the following conclusion is not, at least not completely. Winthrop speaks clearly, that 'So that if we shall deal falsely with our God in this work we have undertaken, and so cause Him to withdraw His present help from us, we shall be made a story and a by-word through the world', meaning that not standing up to the professed ideals will simply result in the loss of providence, not a divine punishment, but will definitely cause the critique and possible animosity of other people, what is corroborated by the later phrase, namely '[by doing so] we shall shame the faces of many of God’s worthy servants, and cause their prayers to be turned into curses'.
It should be noted that the term 'city on the hill' was used by at least one American president before Reagan's tenure, but did not become so common in the popular consciousness. It has been used by John Fitzgerald Kennedy in 1961 precisely in the context presented in Winthrop's sermon, namely:
I have been guided by the standard John Winthrop set before his shipmates on the flagship Arabella three hundred and thirty-one years ago, as they, too, faced the task of building a new government on a perilous frontier. 'We must always consider', he said, 'that we shall be as a city upon a hill - the eyes of all people are upon us'. Today the eyes of all people are truly upon us - and our governments, in every branch, at every level, national, state and local, must be as a city upon a hill - constructed and inhabited by men aware of their great trust and their great responsibilities.
In the Middle Ages the 'city on the hill' was also generally considered to represent Christ himself uniting all the people, as exemplified by the writings of Hilarius, 4th century bishop of Poitiers. His contemporary, Joannes Chrisostom, bishop of Constantinople, interpreted the city from the Gospel of Matthew as metaphor of the Jesus' disciples that were warned by their teacher to watch their faith and deeds. It should be noted, however, that this notion, equating the 'city' with the Jesus, disciples or the Church in general merges the idea of uniqueness (or exceptionalism to use modern political term), as the Church was considered only possibility of salvation and the necessity to watch after one's deeds and make sure they are aligned with professed faith, because the faithful were thought to represent the Church and Christianity in general.
This was also reflected in the Protestant writings. John Calvin wrote that the faithful and especially pastors were 'put into that rank [...] to leave the rest behind and give light from a higher post' and that pastors should 'live in a godly and holy ways, because the eyes of all are upon them as a beacon'. Winthrop himself could have been also inspired by the book In Evangelistam Matthaeum Commentarii by a theologian Wolfgang Mäuslein (also known as Musculus), former secretary to Martin Bucer, a colleague of Calvin (it has been included in a collection Withrop left to Harvard College). In this book, author states that 'Ministers of Christ ought to be in stead of the light, lightening the darkness of this world, because of the doctrine of truth which they show to the whole world'. Likewise, Nicholas Ridley, one of the Oxford Martyrs wrote 'where Christ's sacraments are duly ministered, His gospel truly preached and followed, there doth Christ's church shine as a city upon a hill and a candle on the candlestick'.
So, to sum it up, the original passage from Bible interpreted by the mentioned authors differed quite significantly, but remained more or less true to the intended meaning. It should be noted that although Reagan's rendition of Winthrop's sermon is not exactly faithful, we cannot say that it was incorrect as according to the Reagan's words, both in address of 190 and its farewell speech of 1989 he most likely believed that the country is following its professed ideals (much like aforementioned medieval ecclesiastical officials thought of the Church) and the deliberation whether he was right or wrong is a completely different subject that does not really belong in the discussion concerning the origins of the quoted expression.