Updated Mar 28, 2024 - Culture

Mike Royko's "Boss" crowned best nonfiction book in Chicago history

A photo of the front of Mike Royko's book "Boss."

Photo courtesy of Christine Swenson

We recently crowned the best novel of all time. This week, we turned back to the pages of Chicago literature with a tournament to crown the best work of nonfiction.

The big picture: Chicago has tremendous literary history. Some of the best American authors called our city home.

Catch up fast: There were some heavy hitters in the tournament, but hundreds of Axios Chicago readers ultimately decided that "Boss" was, well, boss.

  • The 1971 book by iconic columnist Mike Royko expertly documents the rise of Mayor Richard J. Daley and his construction of the Democratic Machine that lived on well beyond Daley's reign.

Here's how the tournament played out:

Bracket: Axios Visuals
Bracket: Axios Visuals

How it works: Novels, plays and poems were out. This contest was strictly for history, current events, biographies and memoirs.

  • And, as always, we could only pick 16 for the tournament.

Finalists

  • "The Devil in the White City" vs. "Boss"

Final Four matchups

  • "The Devil in the White City" vs. "Chicago: City on the Make"
  • "Division Street: America" vs. "Boss"

Second round matchups

"The Devil in the White City" vs. "There are No Children Here"

Erik Larson's bestseller straddles Chicago's great World's Fair history with our seedy, murderous past.

Alex Kotlowitz wrote his blistering portrayal of growing up in the Henry Horner Homes after immersing himself in the lives of two brothers struggling with gang violence, family disruptions and poor housing conditions.

"Chicago: City on the Make" vs. "Twenty Years at Hull House"

Nelson Algren's gritty portrayal of the city was initially scorned by city leaders who said the book showed too much reality which, of course, Algren would argue is what makes Chicago, Chicago.

Nobel Peace Prize winner Jane Addams tells the story of the settlement house she built to serve the city's poor and immigrants, and created solutions for integrating newcomers into the city.

"Division Street" vs. "Becoming"

"Division Street" is Studs Terkel's first oral history book and still one of the best books on Chicago history.

Michelle Obama shares her story of how Chicago shaped her, from the long bus rides between the South Side and Whitney Young, to her family's time in the White House.

"Boss" vs. "The Third Coast "

Mike Royko's "Boss," a scathing takedown of Chicago's "machine politics," is not only outstanding, it's requisite reading for anyone living here.

Thomas Dyja makes the compelling case for why Chicago is so central, literally and figuratively, to the boom of culture and commerce in the mid-20th century.

First round matchups

"The Devil in the White City" vs. "Forever Open, Clear, and Free"

Erik Larson's bestseller is the top seed and for good reason. The book combines Chicago's great World's Fair history with our seedy, murderous past. Who wouldn't read that?

In a way, Lois Wille's "Forever Open, Clear and Free" is also about the World's Fair. She chronicles the history of how Chicago has kept the lakefront for the people, which still resonates today.

"There are No Children Here" vs. "Ghosts in the Schoolyard"

Alex Kotlowitz wrote his blistering portrayal of growing up in the Henry Horner Homes after immersing himself in the lives of two brothers struggling with gang violence, family disruptions and poor housing conditions.

Sociologist and former CPS teacher Eve Ewing chronicles the devastating effect the 2013 school closures had on Chicago's historically Black Bronzeville neighborhood.

"Chicago: City on the Make" vs. "County: Life, Death and Politics at Chicago's Public Hospital"

Studs Terkel called Nelson Algren's gritty portrayal of the city "the best book about Chicago." It was initially scorned by city leaders who said the book showed too much reality which, of course, Algren would argue is what makes Chicago, Chicago.

David Ansell started his career at Cook County Hospital and quickly learned the racial and economic disparities of health care in our city, a life lesson he used to advocate for more humane treatment of HIV/AIDS patients and early detection of breast cancer in Black women.

"Black Boy" vs. "Twenty Years at Hull-House"

Richard Wright's "Native Son" was crowned the winner in our fiction tournament; his semi-autobiographical "Black Boy," set on Chicago's South Side, is a portrait of trying to get ahead in a changing city in the early 20th century.

Nobel Peace Prize winner Jane Addams tells the story of the settlement house she built to serve the city's poor and immigrants, and created solutions for integrating newcomers into the city.

"Division Street" vs. "Gang Leader for a Day"

"Division Street" is Studs Terkel's first oral history book and still one of the best books on Chicago history. The truth is that "Division Street" is also a stand-in here for his massive collection, including "Working" and "The Good War."

Sudhir Venkatesh was a grad student at University of Chicago when he befriended a gang leader at the Robert Taylor Homes and embedded with him for a decade to give a sociological view of the drug trade and poverty.

"Becoming" vs. "Lords of the Levee"

Michelle Obama shares her story of how Chicago shaped her, from the long bus rides between the South Side and Whitney Young, to her family's time in the White House.

Two Chicago Tribune journalists report on the rise of a couple of aldermen who ruled the Chicago lakefront during the early 20th century, when it was the destination for anyone looking to unfurl their vices.

"The Third Coast" vs. "The South Side"

Thomas Dyja makes the compelling case for why Chicago is so central, literally and figuratively, to the boom of culture and commerce in the mid-20th century, and includes all the foundational American figures that came up here.

Reporter and writer Natalie Moore is one of the South Side's fiercest advocates and she weaves her own upbringing into this investigation of the effects of deep segregation in Chicago.

"Boss" vs. "American Pharaoh"

Mike Royko's "Boss" is probably the odds-on favorite to win our contest. The scathing takedown of Chicago's "machine politics" is not only outstanding, it's requisite reading for anyone living here.

"American Pharaoh" is the ultimate biography of Richard J. Daley, a Chicago mayor who truly ruled the city.

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