This is something I came up with a short and quick TL (with little detail but lots of fun bits). Inspired by a post I can no longer find where every administration got a mirror version of itself, I challenged myself to make a TL outline where every person who got an electoral vote for President in OTL but was ultimately not elected, ended up serving in the executive office at some point. I have an outline that goes till present day where I managed to fit almost every (about 58) candidate, with the exception of some nominees from 1788, 1792 and 1796, when EVs were cast for President and VP, and from the 1872 and 2016 elections when the circumstances resulted in too many people getting EVs. There are two caveats:
  • For the most part, I cast a wide butterfly net around the world, though as time goes on other “Losers” from around the world will also be favored. I hope this is of interest and I am open to ideas/collaboration.
  • I’m not an expert in early US politics so pardon if the early updates are a bit lackluster. This will get more interesting once it gets going.
Without further ado, here we go: POD – Some political shenanigans between 1786 and 1788, results in George Washington not running for President, while New York manages to choose its electors in time for the 1888-1889 election.

1789 – 1793: John Jay (Federalist, New York) / Robert H. Harrison (Federalist, New York)
Defeated
: John Adams (Fed), George Clinton (anti-Fed), and others.
Once it became clear that Washington was unwilling to seek office, competition became fierce without a figurehead to unite the electors. Very quickly lines were drawn between pro-Federalist and anti-Federalist factions. The pro-Federalists, with a silent endorsement by Washington, were quick to rally behind John Jay and John Adams.
While Adams came in second place, he declined the vice-presidential position, opting instead to serve in the Supreme Court after President Jay extended the offer and nomination.
Known For:
President Jay was a decent and upright man, who history tends to forget was the First Constitutional President of the United States. During his single term in office, Jay opened negotiations with Spain regarding navigation along the Mississippi River and established the First Bank of the United States as a means to establish debt and fund large-scale infrastructure projects.
Most notably, a Bill of Rights was adopted as part of the Constitutional Balance Reform, which included an article for congressional apportionment and limitations on the Federal government. [1]
By the end of his term Vermont, Kentucky, and Westsylvania had been admitted into the Union as states. In response to their admission, Congress reaffirmed the Northwest Ordinance of as a road to statehood for the western territories. [2]

1793 – 1797: George Clinton (anti-Federalist, New York) / John Rutledge (Federalist, South Carolina)
Defeated
: Thomas Jefferson (anti-Fed), Robert H. Harrison (Fed), Edward Telfair (anti-Fed).
John Jay refused to run for a second term, insisting on the need on the nation to frequently renew leadership. Once again this left the electorate wide-open. Efforts to reach across the aisle by both factions resulted in a mixed ticket. Disgruntled and resentful Thomas Jefferson left the United States as foreign minister to France where he felt the republican spirit of revolution was still “uncorrupted”.
Tennessee was admitted into the Union as the 17th state in 1796.
Known For:
A relatively quiet term and acting more like a Federalist when it came to westward expansion.

1797 – 1801: Thomas Pickney (Federalist Virginia) / Oliver Ellsworth (Federalist Connecticut)
Defeated: George Clinton (anti-Fed), Edward Telfair (anti-Fed), Aaron Burr (anti-Fed), Samuel Adams (anti-Fed). Division within the anti-Federalist faction resulted in George Clinton losing his reelection bid and the unexpected election of Thomas Pickney. Clinton, still winning the second largest count of votes, refused the demotion to the Vice-presidency. In response to Clinton’s refusal of the vice-presidential office, Congress passed the Vice-Presidential Election Reform. [3]
Known For:
Pickney's administration refused to continue pay debts owed to France claiming that they had been owed to the monarchy and not the revolutionary regime. The disagreement led to both countries engaging hostilities at sea, and ultimately a declaration of war against the French. The First Franco-American War resulted in the cessation of the Franco-American alliance, and the realignment of the United States with Britain for the duration of the Republican Wars in Europe.

1801 – 1804: Aaron Burr (N. Democrat New York) / Samuel Adams (N. Democrat Massachusetts)
Defeated
: Thomas Pickney (Fed), Rufus King (Fed). Burr unites anti-Federalists into a formal political machine styled the National Democratic Party under the (somewhat hypocritical) guise that Clinton and Pickney had amassed executive power to intolerable heights.
Known For:
The war with France ended, with the restoration of US access to the Mississippi River and France regaining Louisiana from Spain.
President Burr, heavily pushing for westward expansion admitting Erie as a state in 1803 and reorganizing the Northwest and Mississippi territories. The Federal District of Columbia was finally established along the Pennsylvania/Maryland border much to the dismay of those hoping for a Southern capital.
During his last yearn in office, President Burr was shot by a political rival in a “duel”. President Burr survived the immediate shot, but subsequent festering of the wound led to his untimely demise. He became the first President to die in office.

1804 – 1805: Samuel Adams (N. Democrat Massachusetts) / Vacant
Known For:
Being the first VP to ascend the Presidency and maintaining order and re-assuring the country in a time of crisis. ; there is still some debate whether Adams served as President in his own right, or as “acting President”, since the technicality wouldn’t be addressed until the passing of the Presidential Succession Reform in 1843.

[1] Unlike OTL, where amendments are added to the Constitution as a postscript, the Bill of Rights in TLL sets the precedent for in-text reforms instead, making the Constitution more fluid than OTL. Anti-Federalists insisted the Bill of Rights becoming a full in-text Reform as the administration leans more Federalist than Washington’s ever did in OTL. The content is still like OTL’s Bill of Rights even though the style is different, with the addition of the Constitutional Apportionment Article.
[2] They tried twice in OTL and failed, enough political shenanigans for Virginia to give up some additional territory to carve out a new state. I’m mostly doing this for butterflies down the line.
[3] Basically the 12th amendment, but once again this is an in-text reform.
 
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1805 – 1809: Charles C. Pickney (Fed. South Carolina) / Rufus King (Fed. New York)
Defeated
: James Madison (Nat-Dem), Thomas Jefferson (anti-Fed). In the wake of President Burr’s death, the election of 1804 was rather uncertain. Thomas Jefferson returned from France causing a stir amongst the Democrats. This allowed the Federalists to easily sweep the election after James Madison dropped from the race rather than split the ticket with Jefferson.
Known For:
Pickney II is known for escalating newly formed tensions between the US and the increasingly radical French Republic and its Spanish ally. The ensuing Second Franco-American War (AKA The Louisiana War) is relatively short and ends in the United States annexing lion’s share of the Louisiana Territory. Tensions with Britain begin to rise as the rival power moves in to occupy the island of New Orleans and Spanish Florida to prevent further American incursions into Spanish territory. The formal peace treaty between the United States and France won't be signed until 1812 when France's military momentum in the Iberian Peninsula comes to an abrupt end. By then Louisiana was already a de facto American territory.
Meanwhile, in Spanish America, multiple revolts occur sparking wars of independence in the viceroyalties of New Spain, Nueva Granada, and Rio de La Plata.
In 1808 legal importation of slaves into the United States ceased. However, smuggling through Florida and the disputed Gulf Coast territories continues over the next decade.


1809 – 1817: DeWitt Clinton (Dem. New York) / Jared Ingersoll (Fed. Pennsylvania)
Defeated
:
1808: Charles C. Pickney (Fed. South Carolina). Clinton leads a wide coalition against Pickney’s “overstepping” of power during the Second Franco-American war and the administration’s failure to prevent Britain from retaining control of Spanish Florida.
1812: Unopposed. Throughout the 1812 campaign, President Clinton strove to downplay partisan affiliations retaining coalition with Ingersoll and the Federalists.
Known For:
Clinton II was the first President to run for reelection and win.
His first term was marked by the continuation of the Louisiana War. The Treaty of Lisbon is signed in 1812 marking the end of the United States’ involvement in the European Revolutionary Wars. American control over Louisiana is recognized; however, some contention remained over the exact borders and control of Florida.
As the Spanish continue to lose ground in the Americas Spain if forced to secede Florida to Britain in 1813; with the United States and Britain vying for control of West Florida, the Creek and Muscogee tribes led a revolt against encroaching settlement. The resulting Creek Wars lasted well past the Clinton administration and were indirectly responsible for the South voting against the Democrats in 1816.
Clinton II’s time in office term is known for a high number of states admitted into the Union. The former French Territory of Orleans was admitted into the Union after signing peace with France in 1812. His second term in office saw Wabash, Michigan, Mississippi, and Alabama admitted as states. While the territories of Louisiana, Missouri, Marquette, and West Florida were organized.
His Presidency also saw the passing of the Titles of Nobility Constitutional Reform in reaction to people crowning themselves Emperors in the former Spanish colonies and the British “occupation” of Florida.
The Second Bank of the United States was established was also established.

1817 – 1821: Rufus King (Fed. New York) / John E. Howard (Fed. Maryland)
Defeated
: James Monroe (Dem Virginia), the coalition established by Clinton did not last forever; the Establishment of the Second Federal Bank and some Southern resentment over the handling of Indian affairs ultimately created new rifts between the Federalists and Democrats.
Known For:
Recognizing the independence of the Mexican Empire from Spain. Mexico recognizes American control over Louisiana and the border between both countries if formally established at the Sabine River.
A “Final” Treaty with the Civilized Tribes delineates tribal lands within Southern Mississippi and West Florida. Despite the Federal delineation, many Cherokee will “voluntarily” resettle in Louisiana Territory. [1] While the Creek and Muskogee would mostly leave for the interior of British Florida.
The resettlement of the Cherokee, in particular, was a source of strain with the settlers of the Louisiana Territory. Furthermore, the pending admission of Marquette, and Missouri as free states threatened to shift the balance of power away from the slave states. President King had long opposed the expansion of slavery and federal ratio laws and pushed to limit its expansion westward. This ultimately resulted in the passing of The Ozarka Compromise, a series of Congressional Acts that provided for the admission of Marquette and Missouri as free states alongside West Florida, after the Louisiana Territory was split in two (Ozarka and Louisiana) while paving the road for Mayne to become a state whenever either of the new territories became a state.
The Boundary Convention of 1819 delineated the borders between the US and British North America at the 49th parallel and included a provision for the recognition of the US claim to West Florida and British possession of East Florida.

[1] The Chickasaw and Choctaw are the semi-winners here, keeping the core of their 1830 territory intact.
[2] I'll add election maps soon.
 
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