Throughout the Kanto & Johto arcs, Jessie remained limited to only two Pokémon, using Arbok & Lickitung for majority of her journey before accidentally trading Lickitung for a Wobbuffet.
Looking back however, I believe there are fair amount of Pokémon she could've utilized if she took the proper opportunity to do so. As such I'll be making a team using every Pokémon she owned throughout Kanto & Johto, temporary or otherwise.
For the sake of this idea, the reason for her keeping Lickitung would be that the machine they were using to scam trainers actually worked in this version, letting her keep Wobbuffet as well.
First off, we have Porygon Zero from the infamous seizure episode. While it technically belongs to Dr. Akihabara, it obeyed Jessie's commands and fought Ash and Friends without question. In this version the trio flees with it still under their command and adds it to her team.
Next up, Cloyster. This one evolves from the Shellder she caught in the Slowpoke episode. In this version they got blasted off before it turned Professor Westwood V's Slowpoke into a Slowbro. Later on she would get her hands on a Water Stone and evolve it.
With these additional Pokémon on her team, how strong do you think Jessie might have become?
by AlphamonOuryuken24