Mitch Leyor Book Club: Solo Reading 'Trump: The Art of the Deal'

“Trump: The Art of the Deal,” first published in 1987, presents itself as part memoir and part practical guide to negotiation. In candid, conversational prose, Donald J. Trump recounts pivotal moments in his early career—from high-stakes real-estate transactions in Manhattan to the turbulence of acquiring, financing, and restoring landmark properties. Rather than adhering to a strict academic format, Trump intersperses personal anecdotes with lists of “rules” and “steps” he claims underlie every successful deal, inviting readers not just to observe his victories but to understand the mindset he believes makes them possible.

Throughout the book, Trump emphasizes the importance of confidence, timing, and flexibility. He describes how a willingness to walk away, an instinct for leveraging public perception, and a careful attention to detail enabled him to negotiate favorable terms when others saw only obstacles. His narrative often frames each chapter around a specific project—whether the Commodore Hotel renovation or the Trump Tower development—using these case studies to illustrate broader principles he argues are universally applicable. This structure allows the reader to shift seamlessly from concrete examples to generalized tactics.

More than a historical account of one businessman’s rise, “Art of the Deal” positions itself as an accessible playbook for readers from any background. While some anecdotes court controversy or brim with bravado, the underlying message invites readers to adopt a proactive approach to opportunity: think big, prepare meticulously, and maintain the momentum to see a transaction through. Whether judged as a window into Trump’s personal brand or as a compendium of negotiation strategies, the book has endured as a reference point in discussions of leadership, deal-making, and self-promotion.

Solo Reading Guide

Subject: Art of the Deal by Donald J. Trump
Duration: Three days
Format: Individual reading with structured note-taking
Note: Reading times may vary

Day One

Session Length: Approximately 60–75 minutes (flexible)

  1. Introduction and objectives

  2. Read the first section of the text

  3. Take detailed notes on key observations

  4. Summarize primary themes

Day Two

Session Length: Approximately 60–75 minutes (flexible)

  1. Review notes from Day One

  2. Read the next section of the text

  3. Record reflections on style and approach

  4. Outline emerging patterns or strategies

Day Three

Session Length: Approximately 60–75 minutes (flexible)

  1. Review all accumulated notes

  2. Complete the remaining reading

  3. Synthesize overall insights

  4. Draft an action plan or questions for further consideration

Note-Taking Guidelines

  • Include page references for all observations

  • Use clear headings for each section of notes

  • Provide a brief summary at the end of each session

  • Identify at least two points for follow-up or deeper analysis

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