Mailer proclaimed Chicago the great American city in 1968, arguing it eclipsed the dullness of other Eastern cities despite lacking New York's global appeal.
The 1968 Democratic National Convention in Chicago unraveled against the backdrop of national tragedy, culminating in violent confrontations, forever altering the city's image and significance.
As tensions escalated, the Chicago Police Department's harsh response to antiwar protests starkly contrasted with the city's promoted image as the 'city that works'.
This year's Democratic gathering mirrors 1968's ideological rifts and turmoil; historical echoes of protests and violence remind Americans of their fraught past.
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