I like this idea. But maybe we can find Pokemon that more accurately mirror our old dead founders 
$1 Bill (George Washington): We need the OG Pokemon. The one without which, Pokemon wouldn’t exist. The first Pokemon, but also the face that is practically synonymous with Pokemon itself, and that all other Pokemon are compared to. The Pokemon on the $1 Pokedollar must be Pikachu!
$2 Bill (Thomas Jefferson): We need a Pokemon closely involved with the founding of the game. Jefferson wrote the Declaration of Independence, so we need a Pokemon that symbolizes the uniqueness and possibility that Pokemon offers, and how it differs from other similar games. The perfect Pokemon for this must be Eevee!
$5 Bill (Abraham Lincoln): This must be arguably the greatest Pokemon of all time. The Pokemon that led the franchise through a challenging period, but came out on top. A Pokemon which unites. However, this Pokemon can’t be from the original generation. The Pokemon on the $5 Pokedollar must be Rayquaza!
$10 Bill (Alexander Hamilton): A Pokemon involved with the founding generation, but perhaps not as integrally as the others. A Pokemon with essential, but but more behind-the-scenes contributions. One whose contribution and existence still captivates fans to this day. The Pokemon also must be intelligent…there’s only one choice, Dragonite!
$20 Bill (Andrew Jackson): This Pokemon must be a relatively questionable choice on the merits. Perhaps a Pokemon whose claim to fame isn’t all that positive to begin with. A Pokemon that treats other Pokemon harshly. Even though it does so, it has a strong following that resists any attempts to change. The $20 Pokedollar must feature Gengar!
$50 Bill (Ulysses S. Grant): Another Pokemon which must be a leader, but cannot come from the original generation. A Pokemon with a reputation for equality, intelligence, and strength. A Pokemon which can lead others in battle, emerge victorious, and rebuild afterwards. It’s clear, the Pokemon on the $50 Pokedollar must be Lugia!
$100 Bill (Benjamin Franklin): A Pokemon with widespread contributions to the development of the franchise. A Pokemon with contributions not just on the video game, but trading cards, merchandise, and more. Also, this Pokemon must be highly intelligent (sorry Charizard) and use its powers for good (sorry Mewtwo). We only have one choice, on the $100 Pokedollar it must be Mew!