One-Line Summary
A provocative “shadow history” tracing how American presidents—from FDR to Biden—courted, fought, or leveraged organised crime to win wars, elections, and influence.
Opening Impression
Wiseguys and the White House opens like an intelligence brief with a tabloid hook. Eric Dezenhall maps the uneasy marriage of official power and underground muscle, arguing that the presidency’s story can’t be told without the mob’s fingerprints. The tone is brisk, sceptical, and entertaining; the early chapters move from New York docks in World War II to Chicago ward politics with the confidence of a reporter who knows where the bodies are buried—and which claims need caveats.
Synopsis
Dezenhall assembles episodes where presidents or their fixers intersected with wiseguys: wartime cooperation with Lucky Luciano to secure the waterfront; machine politics that helped the Kennedys while later drawing their prosecutorial fire; the nexus of unions, casinos, and construction in the Trump era; and labour power-brokers who shadowed Biden’s early career. Drawing on declassified memos, court files, and interviews, he argues for a pattern of “mutual convenience”: presidents needed votes, security, and deniability; mobsters craved legitimacy, access, and leverage. The book toggles between case studies and big-picture synthesis, emphasising ambiguity where records are thin and pressing harder where documentation is strong.
Analysis
Structure: Modular chapters read as connected dossiers—each closes on a clear finding or a measured question rather than a dramatic flourish. The chronology spans roughly the 1930s to the present, grouped by presidency and theme.
Characterisation: Presidents appear as pragmatists or opportunists depending on the episode; mob figures are rendered as ruthless realists pursuing power by other means. Dezenhall avoids hagiography and, at best, resists easy villains or saints.
Style & Voice: Pacy, reportorial, and laced with noir asides. The prose favours document-driven narrative over speculation, though some links remain inferential by necessity—and Dezenhall flags this.
Themes: Symbiosis of power and reputation; the porous border between legitimacy and illegality; how national security, elections, and labour control create incentives to look the other way.
Verdict
Entertaining, disturbing, and frequently persuasive, Wiseguys and the White House reframes the presidency as a negotiation with America’s underworld. Not every claim is provable beyond doubt, but the aggregate case—sourced, contextualised, and cautiously argued—lands. For readers of political history and organised-crime nonfiction, this is a sharp, highly readable dossier on how deals get done in the shadows.
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