| Timeline: Holmes's Life and Free Speech Jurisprudence, 1841-1935 | p. ix |
| Prologue: The Father of the Modern First Amendment | p. xiii |
| On Life and War | p. 1 |
| Letter to Amelia Lee Jackson Holmes, October 23, 1861 | p. 15 |
| How Our Brothers Fought, July 20, 1864 | p. 18 |
| Memorial Day Address, May 30, 1884 | p. 19 |
| The Soldier's Faith, May 30, 1895 | p. 28 |
| Address at a Banquet for Admiral Dewey, October 14, 1899 | p. 40 |
| Remarks to the Second Army Corps Association, March 13, 1903 | p. 41 |
| General Conceptions: The Early Writings | p. 45 |
| The Gas-Stokers' Strike (1873) | p. 53 |
| The Common Law (1881) | p. 60 |
| Correspondence | p. 75 |
| Privilege, Malice, and Intent (1894) | p. 81 |
| Correspondence | p. 89 |
| The State Court Years: Fettered Freedom | p. 95 |
| Cowley v. Pulsifer (1884) | p. 102 |
| Correspondence | p. 105 |
| Burt v. Advertiser Newspaper Co. (1891) | p. 107 |
| McAuliffe v. Mayor of City of New Bedford (1892) | p. 112 |
| Hanson v. Globe Newspaper Co. (1893) | p. 117 |
| Correspondence | p. 121 |
| Commonwealth v. Davis (1895) | p. 124 |
| Vegelahn v. Gunther (1896) | p. 127 |
| Correspondence | p. 131 |
| The Path of the Law (1897) | p. 138 |
| Commonwealth v. Peaslee (1901) | p. 156 |
| Supreme Court Opinions: The Early Years | p. 161 |
| Patterson v. Colorado (1907) | p. 170 |
| Peck v. Tribune Co. (1909) | p. 177 |
| Correspondence | p. 179 |
| Gandia v. Pettingill (1912) | p. 181 |
| Fox v. Washington (1915) | p. 185 |
| Jay Fox, ôThe Nude and the Prudesö (1911) | p. 190 |
| Toledo Newspaper Co. v. United States (1918) | p. 192 |
| Correspondence | p. 195 |
| Natural Law (1918) | p. 199 |
| Correspondence | p. 203 |
| Supreme Court Opinions: ôWhen a nation is at warö | p. 205 |
| Baltzer v. United States (1918) | p. 215 |
| Schenck v. United States (1919) | p. 219 |
| Correspondence | p. 224 |
| Circular, Long Live the Constitution of the United States (1917) Frohwerk v. United States (1919) | p. 241 |
| Debs v. United States (1919) | p. 246 |
| Correspondence | p. 250 |
| Supreme Court Opinions: Experimenting with Freedom | p. 262 |
| Abrams v. United States (1919) | p. 271 |
| Correspondence | p. 277 |
| Correspondence | p. 289 |
| American Column & Lumber Co. v. United States (1921) | p. 308 |
| United States ex rel Milwaukee Social Democratic Publishing Co v. Burleson (1921) | p. 312 |
| Leach v. Carlile (1922) | p. 317 |
| Correspondence | p. 318 |
| Gitlow v. New York (1925) | p. 321 |
| Correspondence | p. 324 |
| United States v. Schwimmer (1929) | p. 334 |
| Correspondence | p. 336 |
| Adieu, March 8, 1931 | p. 342 |
| Epilogue: The Long Shadow | p. 349 |
| Holmes on Free Speech and Related Matters: Selected Quotations | p. 385 |
| Holmes's Supreme Court Voting Record in Free Speech Cases | p. 398 |
| About the Editor | p. 401 |
| Index | p. 403 |
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