1 - The Election of 1844
(Note: the following is an exploration of how John Tyler could have won the election of 1844, and some of the results of what might have happened afterwards, it is not wholly realistic, and is in fact inspired by a game of President Infinity that I played as Tyler and managed to just barely win. After I played, I recorded the results and began delving into any possible way this could have happened. What I have produced is the following. As I say, it is not entirely realistic, but neither I did not feel right putting it in the ASB forum)
...and Tyler, Too!
What if John Tyler ran in 1844?

What if John Tyler won in 1844?

1844 is a year that has gone down in history as one of the most chaotic, head scratching and downright stupid years in history. Most people know the story to some extent, an incredibly unpopular incumbent president, viewed by many as illegitimate, turned a modest base of support and a single-issue candidacy into a second-term in his own right by stealing the election right out from under the noses of his opponents, through determination and sheer dumb luck.

On May 30, 1844, John Tyler, the 10th President of the United States, accepted calls from his supporters to run for president on his own terms. The "National Democratic-Republican Party" held a convention in Baltimore, Maryland, just a short distance from the Democratic Party's own convention. Tyler would later write that this was originally meant to be merely a stunt to get the Democrats to nominate someone who would support the annexation of Texas - but when he received the news that Martin Van Buren had received the nomination for President, Tyler knew he had to commit to the race wholeheartedly. He selected a running-mate, Senator Thomas Hart Benton of Missouri, who accepted, and began waking up the South to secure support for his agenda...

Crazy, Stupid Campaigning
What Tyler soon realized was that there was simply no way he could win the election outright. But with both Van Buren and Clay opposing the annexation of Texas, he had an opening in the southern states, if he could get his foot in the door, he very well could force the election to the House and use whatever influence he would gain to broker a deal for annexation. Things would have to go just right though.

The campaign season itself was a mess. Van Buren was abandoned en masse by Southern Democrats, Clay assumed he would win all along with the apparent Democratic schism, all while Tyler amassed support.

On election day, nothing happened like anyone might have expected.

Henry Clay assumed he would hold enough support among Southerners to hold the balance after Tyler took votes from mostly Van Buren. He was wrong.
Screenshot_2019-09-21 Electoral College Calculator and Map Generator.png

Needed to Win: 138 EV
Clay-Frelinghuysen (W) - 119
Tyler-Benton (D-R) - 84
Van Buren-Wright (D) - 72

Popular Vote:
Clay-Frelinghuysen (W) - 1,188,720 (44.0%)
Van Buren-Wright (D) - 875,330 (32.4%)
Tyler-Benton (D-R) - 559,239 (20.7%)

Just a reminder that these results are all taken from a game of President Infinity, which is not necessarily an authoritative source on accurate election results, but I have accepted these as the results for this particular universe

For the second time in twenty years, no candidate had reached the required number of electoral votes to win the presidency. Clay was dumbfounded, Van Buren was ecstatic, Tyler was stressed.

For Van Buren - this was great - Tyler was practically unelectable in his eyes and the Democrats controlled Congress.

For Clay, he felt that he had already been robbed of his chance - with a Democratically-dominated House, he was nearly guaranteed to lose. Since the House could choose any of the top three candidates, technically any of the three men could win.

In the Senate, things were less complicated, as the Whigs held a majority. They elected Theodore Frelinghuysen over Thomas Hart Benton in a 27-24 vote.


Won't You Steal This Election With Me?
John Tyler had nothing at all to do with winning the election of 1844. In fact, it was won by two members of Congress who acted with no direction from the President whatsoever: Littleton Waller Tazewell of Virginia and John White Stevenson of Kentucky.

They had to convince fifteen states to vote for the unpopular incumbent, rather than Van Buren or Clay. Virginia, North and South Carolina, Georgia, Alabama, Mississippi, Louisiana, Missouri, Arkansas, and Tennessee were convinced to support him with some small effort, mostly by reminding them of the Texas issue and that what was at risk here was American, not to mention Southern pride itself!

Still in need of five votes, they decided to approach three delegations in turn, the Illinois, Indiana, and Michigan delegates and present them with an idea. Instead of voting for Van Buren, as they planned, they should instead vote for Tyler on the first ballot in order to ensure Van Buren's victory. How would this assure his victory? Well, they argued, at present there was still a significant risk of Clay winning the Presidency and even if they were in fact friends of Tyler, what they wanted most of all was for a Democrat, or at least not a Whig to win, and since Tyler obviously wouldn't win, they were left to support Van Buren. They claimed that under the current electoral rules, no one will win enough votes on the first ballot to claim the presidency - but that means that on the second ballot, only the two candidates who won the most votes in the first ballot would be under consideration. Under this setup they said, once Tyler was knocked out, it was possible for Clay to win - but by switching their votes to Tyler instead of Van Buren, they would be setting the vote order as follows: Van Buren, Tyler, Clay. Then, once Clay is removed, Van Buren's victory is practically assured.

There are two problems with their argument. One, Tyler was actually currently ahead in state votes by their count. Two, and most importantly. That isn’t how contingent elections are conducted. If, in fact, there had been a second round, all three candidates would still be eligible. But, it worked, and all three delegations were convinced to vote for him this way. They still needed two more votes for Tyler to win, and it would surely not be possible to try the same tactic on the second ballot, but the time had come for the first round of voting, and they had tried their hardest - so surely Tyler was now doomed, right?

Not quite.

In both the Pennsylvania and Kentucky delegations, there were arguments over whether to support Van Buren or Clay. While Clay had won both of their electoral votes, their state delegations were equally comprised of Democrats and Whigs, and neither party was willing to budge, even in Kentucky, Clay's home state. And so, in Kentucky's delegation, John W. Stevenson put forward that, since they were at an impasse, and that ballot was nearly about to be conducted, they should simply vote for Tyler on the first ballot - it's not like he'll win anyway, right? Then they'll have time to decide exactly who to vote for before the second ballot, if they needed to. In the Pennsylvania delegation, Henry Nes, the Independent Democrat, put forward the exact same solution, and both delegations simply accepted this solution.

And so, when the votes were tallied... John Tyler had taken 15 state delegations' votes - a majority, and was elected to a full term as President of the United States. Through Sheer. Dumb. Luck.

Screenshot_2019-09-21 Editing 1844 United States presidential election - Wikipedia.png

*typo in wikibox - Clay takes five states in HR, Van Buren takes six
On the House results:
I did take some liberties here, as in the game itself Van Buren took the election, but I thought that wasn't good enough for me so I decided to concoct this bizarre experience as a kind of brain exercise. Either way, it accomplishes my goal of getting Tyler that second term.

On what's next:
I have the basics of Tyler's term as president planned out and mean to flesh them out more before I start posting them as actual updates. Please be patient with me, I am most definitely not an expert on this era but I am doing research to hopefully not screw it up haha
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2 - Texas and Oregon
Everything Turned Out Better Than Expected
Once Tyler was announced as the victor of the election, all hell broke loose. On the House floor, Tazewell and Stevenson had to be evacuated or risk lethal harm, and at least six brawls broke out in the span of the next ten minutes. Across the country, there were similar reactions as Whigs and Democrats alike began to see just how much had been taken from them. They now had a President, previously already unpopular, who had received only one-fifth of the nation’s votes, less than half of what Clay had received, and Henry Clay and Martin Van Buren were furious.

Clay approached Van Buren to discuss a joint suit challenging the election in the House, but it never came to pass.

After realizing that his position was in fact secure, Tyler, still amazed he had won, submitted once more, the Texas statehood offer to the Senate and the House on March 5, 1845. Now that the Democrats had control of both houses of Congress, Tyler felt he could work with them on foreign policy. He was right.

Both houses voted immediately as their first order of business, though they felt robbed of the presidency, Democrats as a whole were in favor of annexation, despite what Martin Van Buren’s views were. In the House, the measure passed 128-99 and in the Senate 28-26, and on November 13, 1845, Texas officially became the 28th State.

Meanwhile though, Tyler still had to deal with the fact that he was, in general, reviled. Tyler was encouraged by Texas though, and moved to make further gains in the foreign arena to accomplish Manifest Destiny. In January of 1843, he had tasked Secretary of State Abel Upshur with resolving the “Oregon Question” with Britain. By the end of 1844, the United Kingdom and the United States had worked out a treaty detailing their border in the Oregon. The Upshur-Pakenham Treaty was generally favorable to the United States, continuing the border at the 49th parallel. In early 1845, the Senate ratified the Treaty by the necessary ⅔ majority.

In short, no major changes to history regarding expansion yet, other than a slightly earlier Oregon Treaty and Texas annexation. And yes, ITTL, Abel Upshur is still kicking

EDIT: I previously had stated that Upshur was working on Oregon since 1845 but that was a mistake, he'd been historically already working on it prior to the Princeton disaster.
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SO, Upshur didn't die in 1844, so I assume that the Princeton disaster didn't happen then?? So Calhoun is not Sec of State?

Correct on both fronts my friend. John C. Calhoun is still in the Senate ttl.

Thomas Walker Gilmer is also still Secretary of the Navy
3 - The California Crisis (Part 1)
The California Crisis
Part One

In December of 1844, President John Tyler of the United States and his Secretary of State, Abel Upshur, feeling secure in their position with the United Kingdom, began making plans for the seizing of Northern Mexico, primarily the states of Alta California and Santa Fe de Nuevo México, but with further plans to hopefully gain even more, reaching into Baja California and Sonora and parts of some of the other Northern states of Mexico.

Tyler sent an offer to the Mexican President, Jose Joaquin de Herrera, in exchange for $15 million, Mexico would sell Alta and Baja California and Santa Fe de Nuevo México to the Americans. Herrera, already in danger of being overthrown, rejected this offer, but invited Tyler to come personally negotiate with him to bring a peaceful resolution to the crisis, even as Mexico continued to raise forces in anticipation of America's possible invasion.

Tyler had not anticipated this. He knew he could not leave to negotiate this himself but was certainly interested in whatever it was Herrera had to say that was so important he desired to meet with him personally, and so on Februrary 23, 1845, Secretary of State Abel Upshur himself arrived in Mexico City to treat with the Mexican President.

What exactly occurred in the meeting that unfolded afterwards is lost to history, but whatever the case, it is widely documented that as soon as the meeting was over, in just over an hour, Upshur immediately made preparations to return to Washington.

And the next day, Herrera was dead.

Some have suggested that the United States assassinated Herrera to provoke Mexico into declaring war, but it is also possible that supporters of former Mexican president Antonio Lopez de Santa Anna had him killed off, as within the week, Santa Anna arrived back on Mexican soil and was named his successor.

Whatever the case, when Upshur returned to the capital he presented the Senate and Tyler with a treaty, negotiated by him and Herrera which granted the United States all of Alta California and Santa Fe de Nuevo México in exchange for $25 million. Tyler, though worried at such a large sum, was ecstatic, and urged the Senate to approve the treaty, which it just barely did in a 36-16 vote.

Naturally, when Santa Anna received word of the "supposed treaty," he claimed that the United States had fabricated it completely, and that "noble Herrera" would never have approved such a "blatant attack on Mexico's sovereignty." And even so, there was no approval by any other Mexican authority. Regardless, the United States held firm in its position that the treaty was valid, and the California Crisis was underway.