The King of Chicago is the story of a father-son relationship as real and hugely loving as that in Philip Roth's Patrimony. At its heart is a young son who tries furiously to heal his father from a violent childhood inside a Chicago orphanage. The orphanage, the Marks Nathan Home, still stands today on the West Side of Chicago, marked by a tarnished, barely legible plaque. Once home to 14,000 Jewish orphans, it is now just another barely remembered relic of a great city. Using original articles from the orphanage newspaper, Friedman attempts to reconstruct and understand his father's childhood, a time that his father never discussed.

Expanding its reach, The King of Chicago becomes a multigenerational saga of Jewish life, moving from a mysterious little man named Kasiel, who arrived in the Port of Baltimore in 1903 with two dollars to his name, to the factory floor of a scrap paper business, a golf course where children played without knowing the rules, and a home on the North Shore among fellow immigrants looking for something better for their children.

At its core, this memoir is both a snapshot of immigrant life in Chicago in the early twentieth century and a poignant reminder about the need to never forget who you are and where you come from.