The best books on political bosses

The Books I Picked & Why

All the King's Men

By Robert Penn Warren

Book cover of All the King's Men

Why this book?

At my first paid reporting job, one college summer for the Lake Charles (La.) American Press, a veteran reporter told me that if I wanted to cover politics, in Louisiana or anywhere else, I had to read Penn Warren’s novel, a classic based on Huey Long’s life. I got a copy – and was hooked from the opening, when Sugar Boy, the boss’s chauffeur and gunsel, whipped their Cadillac around an oncoming gasoline truck and stuttered, “The b-b-b-b-bas-tud . . .” Penn Warren, a poet, brought to life the realpolitik and machine politics I’d studied. He showed me, through Willie Stark’s devotees, the human drive to be part of something bigger than yourself, which can make the downtrodden easy marks.


When you buy a book we may earn a small commission.

The Gay Place

By Billy Lee Brammer

Book cover of The Gay Place

Why this book?

Brammer’s novel has resonated throughout my career, warning of almost inevitable disillusionment with a political powerhouse. Brammer had served as a top aide to Lyndon Johnson, on whom he based Arthur Fenstemaker, a star as bright as Penn Warren’s Willie Stark. The Gay Place spoke to me even more directly, focusing on minor politicos and their ambitions, frailties, and humanity. And the book drove home, through a pervading sadness, the anomie that rises from disillusionment. Brammer’s “Flea Circus” metaphor continues to amuse and bum me.


When you buy a book we may earn a small commission.

The Last Hurrah

By Edwin O'Connor

Book cover of The Last Hurrah

Why this book?

James Curley, former Boston mayor, Massachusetts governor, and jailbird – not in that order – was as grand a politico as Huey Long or LBJ, and O’Connor’s novel based on his career holds its own with the classic romans à clef on those two. Frank Skeffington was also a self-made populist, but O’Connor’s book centers on big-city politics and ethnic tensions, which were more immediate to me – I grew up in New York City. Skeffington, a charmer, considered himself innately decent, an honorable man forced to play a dirty game, which made one of my father’s maxims echo: Beware of anyone with a clean conscience.  Skeffington honed words as weapons, which helped me appreciate the power of a good quip.


When you buy a book we may earn a small commission.

Plunkitt of Tammany Hall: A Series of Very Plain Talks on Very Practical Politics

By William L. Riordan

Book cover of Plunkitt of Tammany Hall: A Series of Very Plain Talks on Very Practical Politics

Why this book?

Plunkitt infected me with “the political bug.” George Washington Plunkitt’s “very plain talks on very practical politics” showed me the joys of playing the political game, of devising and executing strategies and tactics, of outwitting opponents. I first read Riordon’s classic for grade school and loved its gritty romp through turn-of-the-century New York. I reread the book for a college history course and came to appreciate politics as the art of the possible – and to see the innate conflict between ambition and conscience. After seven years in journalism, I “crossed to the dark side” and became a political operative, partly because Plunkitt had shown me that playing politics can be far more rewarding – and fun – than watching it.


When you buy a book we may earn a small commission.

Huey Long

By T. Harry Williams

Book cover of Huey Long

Why this book?

I began reading Williams’s biography as research for a recent historical novel, scanning passages listed in the index. Soon enough, I was gulping whole sections and chapters; I couldn’t stop reading the thing.  Williams reminded me how exuberant political narrative nonfiction can be and taught me as much about writing as about Huey Long. He showed ways to showcase characters’ traits and tells, portraits-in-miniature, in a “God is in the details” vibe. He showed how to set a story in its historical context while also using history as a mirror for contemporary times. And, through Long himself, Williams made me again admire the boundless audacity and ambition that I’d never possessed – and again made me thankful for its absence.


When you buy a book we may earn a small commission.

Closely Related Book Lists

Distantly Related Book Lists