| Family Trees | p. xii |
| Timeline | p. xix |
| The Borgia Problem: An Introduction | p. xxvii |
| Pope and King, Friends No More | p. 43 |
| Pius II: Troubles Rumored and Real | p. 100 |
| Maps | p. xxiii |
| Surviving | p. 83 |
| Prologue: One Whom All Did Fear | p. 3 |
| Alonso: From Out of Nowhere | p. 7 |
| Background: Il Regno-The Kingdom | p. 38 |
| Background: The Men in the Red Hats | p. 65 |
| The End of the Beginning | p. 71 |
| A Most Improbable Pope | p. 9 |
| Rodrigo: A Long Apprenticeship | p. 81 |
| Background: The Road to Rome | p. 20 |
| Surprises, Disappointments, Hope | p. 29 |
| Background: Amazing Italy | p. 52 |
| Family Matters | p. 57 |
| Background: The Eternal City, Eternally Reborn | p. 97 |
| Paul II: The Poisoned Chalice | p. 118 |
| Background: The Inextinguishable Evil-Heads | p. 129 |
| Sixtus IV: Disturbing the Peace | p. 134 |
| Background: War, Italian Style | p. 148 |
| Innocent VIII: Plumbing the Depths | p. 154 |
| Alexander: Pope at Last | p. 171 |
| The Best Man for the Job | p. 173 |
| Background: Madness and Milan | p. 194 |
| The Coming of the French | p. 201 |
| Background: Florence: An Anti-Renaissance | p. 220 |
| The French Depart | p. 224 |
| Background: The Paternity Question: An "Apology" | p. 239 |
| A Shattering Loss | p. 248 |
| Background: The Young Ones | p. 265 |
| Valentino | p. 270 |
| Cesare: Caesar or Nothing | p. 293 |
| The Landscape Changes | p. 295 |
| Background: Venice, Serene No More | p. 312 |
| Conqueror | p. 316 |
| Background: The Angel's Castle | p. 334 |
| Background: The Newest Profession | p. 351 |
| Settling Scores | p. 354 |
| Man of Destiny | p. 369 |
| Background: Superstitions: Another Side of the Renaissance | p. 380 |
| Alone | p. 384 |
| Aftermath | p. 409 |
| Examining Old Assumptions | p. 419 |
| Notes | p. 433 |
| Bibliography | p. 451 |
| Background: Il Papa | p. 114 |
| "Longing for Greatness and Renown" | p. 337 |
| Background: The Great Discoveries | p. 365 |
| Index | p. 457 |
| About the Author | p. 479 |