Jefferson:

Species- I chose Gholdengo for Jefferson because I feel as if it’s his perfect match. First of all, Gholdengo is quite literally made of money and Jefferson was born into wealth. Also, according to Gholdengo’s pokedex entries it is friendly and well-liked by other Pokemon. The song What’d I Miss is just straight Jefferson glaze and shows that he is quite the popular guy. I think Gholdengo’s popularity amongst other pokemon and Jefferson popularity amongst his fellow Virginians go hand in hand. I can’t lie though, another big factor for this pick was Gholdengo’s role in VGC. In VGC Gholdengo is an annoying Pokemon that loves setting up with the move “Nasty Plot” and sweeping with “Make it Rain”. Mainly the fact that Gholdengo is such a prominent nasty plot user is the second biggest I chose it. If the entirety of Room Where It Happens and Washington on Your Side isn’t just one big nasty plot set up then I don’t know what it is. This choice was just so instant to me that I don’t think I could imagine another pokemon as Jefferson if I tried.

Moveset- Nasty Plot, as I said above, is representative for Jefferson’s schemes against Hamilton in the musical. Any good Nasty Plot can’t be used without Make it Rain. Trust me it’s a powerful combination. Make it Rain is also just pokecoins falling from the sky and that move screams Jefferson type privilege. (and it’s Gholdengo’s signature move it’d be weird not to add it) Thunderbolt is added solely because of the “bring the thunder” line. I wish Gholdengo learned the actual move called thunder but thunderbolt is close enough. He has Flash Cannon because musical Jefferson is, well, extremely flashy. I imagine Flash Cannon to be a move that is large in size and it makes the perfect obnoxious finisher move for Jefferson to use in battle.

Nature- Jefferson has the “Jolly” nature which raises speed and lowers special attack. I headcanon Jefferson in battle to prioritize moving first (like him getting to speak first in cabinet battles). The drop in special attack doesn’t bother him due to him already raising his special attack multiple stages while using Nasty Plot.

Madison:

Species- The idea of Beartic Madison was entirely inspired by @/jesterprivilege’s Pokemon trainer AU I won’t lie. I was looking for inspiration and went down a rabbit hole on her account then we got here. The idea of Madison evolving from a sick Cubchoo into an even worse Beartic was pure gold. Now, I know that canonically Cubchoo isn’t actually sick but Madison is an exception because I said so. Also, I’ve been on my musical height Madison shit this Hamilton era so Beartic was perfect to fit the “taller than Jefferson” criteria.

Moveset- Since Madison is constantly poisoned the equivalent of him spreading his disease would be the move Toxic. I visualized him just vomiting on his enemy. Maybe shooting a straight snot rocket into their mouth? Idk how it would look for a non poison type to use a poison move but I don’t want to imagine it. I gave him the move Bide because Beartic’s lowest stat is its speed stat meaning I imagine Madison to move last during battles. With all the damage he would take I think Bide would be the best way for him to utilize his high attack stat and low speed stat at the same time. Blizzard and Sheer Cold are on the same boat here. Both are special attacking moves with low accuracy but deal a ton of damage. Beartic is not built to be a special attacker but in my AU the Pokemon aren’t running their base stats. Every Pokemon’s highest and lowest stat is kept the same but the other stats are different based on the Pokemon. Madison’s special attack stat is higher than a usual Beartic but it comes at the cost of his special defense and hp. I gave Madison these high risk moves because I don’t see him as much of a fighter. Although he has the strength to do so he would much rather talk it out. I like to imagine he scarcely uses those moves but somehow always hits (cough...skill swap…cough cough)

Nature- Madison has the “Bold” nature which increases defense and lowers attack. Since I don’t see Madison attacking much, a drop on his attack would be reasonable. Increasing defense can help him tank hits which would be useful for Bide and for having a slim chance of surviving with his abysmal amount of hp.

Burr:

Species- Choosing Burr’s species probably took the longest out of every character. I had a lot of debate on what I wanted my choice to represent. The only criteria I had is that it had to be a psychic type because psychic type Burr speaks to my soul. Anyways, I ended up with Wobbuffet because it is a pokemon that is built to endure hits and unleash the damage after the fact. I think this can represent Burr’s constant failures throughout the musical and how he comes back after taking enough “hits” and deals his own damage to Hamilton. That wasn’t explained the best but I hope y’all get the jist. Also, Wobbuffet is called the “patient” pokemon and I would describe the “Talk Less. Smile more” mentality as a test of patience if anything. Furthermore, Wobbuffet’s entire thing with hiding its tail is quite literally the putting up a front metaphor. Idk I’m not one of those cool ass people who can analyze Burr on a spiritual level but I try…

As an apology for not being able to finish here’s the scrapped act 2 drawing