If we trace the origins of the phrase “city upon a hill” which was taken from Matthew chapter 5 of the Bible, the connotations are made pretty evident. Jesus, the speaker, is encouraging Christians to becoming a shining example of holiness; to practice all of the admirable qualities the “blessed” have (Matthew 5:3-11). Just as a city upon a hill cannot hide, Jesus asks that Christians therefore “in the same way, let your light shine before others that they may see your good deeds and glorify your Father in heaven (Matthew 5:16). This request isn’t meant to be one that asks Christians to boast about their good works, in fact in the very next chapter of Matthew, Jesus admonishes: “Be careful not to practice your righteousness in front of others to be seen by them. If you do, you will have no reward from your Father in heaven” (Matthew 6:1). The city upon a hill, in this sense, is then meant to serve as a “beacon”, and a Christian is not necessarily meant to be a flashy, pompadour, and self-righteous individual, but one that is a role model for goodness and holiness. Obviously we can’t ignore the denotative qualities of the phase “city upon a hill”. A city is a group of individuals coming under one nation; similarly, Christians recognize themselves as the people of God, and so there is a sense of nationality amongst the group. Of course, I believe that this second connotation that we may have derived from the phrase takes second chair. I say this primarily because how the metaphor was wedged in between two other metaphors (the salt and light, the candle and bowl) that were all essentially conveying the same message. This message, as we know, was summarized in Matthew 5:16.
After acknowledging that “city upon a hill” has two meanings, the latter not so important, it’s interesting that Winthrop chose to use the phrase. This isn’t to say that John Winthrop was hijacking the phrase and using it out context, only that he wasn’t using the primary metaphor. If we can recall, John Winthrop in his sermon, A Model of Christian Charity, uses “city upon a hill” to describe the colony being established in America. He asks his followers to obey certain cardinal values, for example “Justice and Mercy” (34), and treat others the way you want to be treated (35). The motive behind this sermon, is to encourage the people to work together, so that England can see that they are doing just fine on their own: “For wee must consider that wee shall be as a citty upon a hill. The eies of all people are upon” (47). Winthrop’s sermon is optimistic, it encourages the people that they too can be a beacon of hope to other pilgrims, provided that they follow a certain set of ideals and more importantly, get along with each other (which ties in the nationality part).
In regards to modern usage of the phrase, if we can successfully separate the fact that John Winthrop was a fervent Christian, knowingly using the phrase with religious connotations, but moreover to encourage a pride of nationality, we can see that modern usage doesn’t do justice to Winthrop’s meaning and definitely not Jesus’. Winthrop, like Jesus was arguing for sense of morality, a goodness that could bring the people together and serve as a beacon, Regan on the other hand, focuses on the city aspect of the phrase. He remarks that we’re different, coming together under the same nation, but that we are a melting pot who is open to everyone. In the speech, he makes it clear that America is a beacon of freedom and that is the only attribute, not that it’s just or that its good or that it’s moral, as Jesus and Winthrop alluded to. Similarly, Obama’s farewell speech took on the same verbiage that America was a beacon of freedom, a melting pot, etc. which changes the original meaning significantly, but not exceptionally. Obviously secular people may disagree, arguing that they’re essentially equal to each other, but as a Christian myself I can see the ways the Word of God has been augmented to fulfill a separate agenda, in the case of Regan and Obama, almost completely. Of course, there are parallels, the ones I have aforementioned, and so I can definitely see the similarities though they are broad.