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Lindsey Naegle should have a tough, female pokemon like Tsareena. One that can put its foot down in the business world.
Frink would have very experimental Pokemon and steel types! I think Meltan is a good fit for him! It's a little odd and cute like him! Also it's kinda like Flubber!
(Repost) Krustylu 2! Pennycandy with Munna! Sideshow Mel with Alolan Marowak!
Not shown: Mr. Teeny and Aipom!
KRUSTY! (Reposting him) would have circus pokemon that are good in his show! Popplio uses water gun like seltzer! Phanpy uses rollout on Sideshow Mel!
Cecil would rival his brother with either Pinsir or Omastar (I think Pinsir because it matches his hair?). With Galar Weezing, it is explosive but also "fancy" like him.
Sideshow Bob would have sharp, dangerous pokemon. I can also see him having dragon types? Things that are VERY theatrical and unappreciated. Like Druddigon! He goes for AESTHETIC!
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Michael would have cute pokemon that are associated with cooking! Like plants and mushrooms! But they both can use poison attacks are dangerous! TINY AND DANGEROUS!
I think Fat Tony should have a Trubbish because he is in waste management business. He also has a Ponyta for racing. I think if he had to fight he'd have strong poison types, but for appearances, he has small pokemon to look more innocent around the police.
I was also thinking Scrafty for Legs? I think he'd have fighting types. He definitely has stronger pokemon where Louie has faster ones. Johnny is more into aesthetics (but still strong), and Frankie would not fight. Frankie maybe has a staryu? He's flashy but not confrontational.