| Image | Voter | Winner | Loser | Reason |
|---|
 | Professor Frink | Bill of Rights | Emancipation Proclamation | Oh, glayvin! The Bill of Rights lays the foundational framework for all those nifty freedoms and protections, ensuring a society where individuals can pursue happiness and innovation! |
 | Alex Trebek | Emancipation Proclamation | Prohibition Repeal | The Emancipation Proclamation was a historic step toward freedom and equality, a game-changer that reshaped America at its core. |
| Alex Trebek | Voting Rights Act | Emancipation Proclamation | While both are pivotal, the Voting Rights Act directly empowered individuals with the ability to shape democracy, making it a game-changer in practice. |
 | Linus Torvalds | Emancipation Proclamation | Prohibition Repeal | Freeing people from slavery is a monumental step for humanity, way more impactful than repealing a law about booze. |
 | Guido van Rossum | Emancipation Proclamation | Affordable Care Act | Dude, the Emancipation Proclamation was a massive leap towards human rights and freedom, laying the groundwork for equality in America. |
 | Pythagoras | Universal Suffrage | Emancipation Proclamation | Yo, universal suffrage gives everyone a voice, not just freedom, so it's like the ultimate power to the people. |
| Alex Trebek | Declaration of Independence | Emancipation Proclamation | The Declaration of Independence laid the groundwork for America as a self-governing nation, setting the stage for future advancements like the Emancipation Proclamation. |
 | Charles Darwin | Civil Rights Act | Emancipation Proclamation | Mate, the Civil Rights Act was like the finch's beak evolving for a new era, providing comprehensive rights and addressing discrimination more broadly across society. |
 | David Macaulay | Emancipation Proclamation | Prohibition Repeal | The Emancipation Proclamation was a monumental step towards ending slavery and promoting human rights, which outweighs the repeal of Prohibition in terms of societal impact. |
 | George Orwell | Civil Rights Act | Emancipation Proclamation | While the Emancipation Proclamation was a monumental step in ending slavery, the Civil Rights Act tackled a wider range of discrimination, making it more comprehensive in promoting equality. |
 | Archimedes | Universal Suffrage | Emancipation Proclamation | Yo, Universal Suffrage is the real MVP 'cause it gave everyone a voice, making democracy legit for all genders and races. |
 | Grace Hopper | Declaration of Independence | Emancipation Proclamation | As a history-loving nerd, the Declaration of Independence kicked off the birth of the whole nation in glorious rebellion, setting the stage for everything else, including future freedoms like those in the Emancipation Proclamation. |
 | David Foster Wallace | Emancipation Proclamation | Prohibition Repeal | Freeing people from chattel slavery is a bigger win for humanity than being able to legally grab a drink. |
| Charles Darwin | Emancipation Proclamation | Social Security Act | The Emancipation Proclamation was like a seismic shift in human rights, ending slavery and redefining freedom, which aligns with my pursuit of understanding human evolution and societal progress. |