| | Cast of Characters | p. ix |
| | Introduction | p. xix |
| | East Boston to Cambridge to Brookline | p. 1 |
| | Dunganstown to East Boston | p. 3 |
| | School Days | p. 16 |
| | Starting Out | p. 32 |
| | War | p. 47 |
| | Making a Million | p. 58 |
| | Hollywood | p. 83 |
| | "My Own Master in My Own Business" | p. 85 |
| | Hollywood | p. 105 |
| | Gloria and Rose | p. 128 |
| | Last Exit from Hollywood | p. 149 |
| | Washington | p. 165 |
| | On the Roosevelt Train | p. 167 |
| | Waiting for the Call | p. 185 |
| | To Washington | p. 204 |
| | Reelecting Roosevelt | p. 238 |
| | Maritime Commissioner | p. 254 |
| | London | p. 281 |
| | A Plainspoken Ambassador | p. 283 |
| | A Rather Dreadful Homecoming | p. 312 |
| | Munich | p. 323 |
| | The Kennedy Plan | p. 348 |
| | Sidelined and Censored | p. 371 |
| | "This Country Is at War with Germany" | p. 399 |
| | The Lives of Americans Are at Stake | p. 408 |
| | Defeatist | p. 427 |
| | The Fall of France | p. 444 |
| | The Worst of Times | p. 457 |
| | There's Hell to Pay Tonight | p. 473 |
| | Washington, but Briefly | p. 487 |
| | Home Again | p. 489 |
| | The Man Who Out-Hamleted Hamlet | p. 505 |
| | Palm Beach and Hyannis Port | p. 523 |
| | A Forced Retirement | p. 525 |
| | War | p. 538 |
| | "A Melancholy Business" | p. 570 |
| | The Candidate's Father | p. 591 |
| | Family Matters | p. 610 |
| | "The Great Debate" | p. 632 |
| | The Next Senator from Massachusetts | p. 652 |
| | Retirement | p. 671 |
| | Making Money and Giving It Away | p. 692 |
| | The Catholic Candidate | p. 709 |
| | Electing a President | p. 726 |
| | "He Belongs to the Country" | p. 749 |
| | "No!" | p. 775 |
| | Acknowledgments | p. 789 |
| | Notes | p. 793 |
| | Bibliography of Works Cited | p. 829 |
| | Index | p. 835 |