Ash Ketchum has handled many enemies throughout the Pokémon anime, but none are quite so iconic as the Team Rocket trio of Jessie, James and Meowth. From the first season in Kanto's Indigo League to the current adventure in Pokémon Journeys, Ash has faced off against Team Rocket regularly. However, the well-known antagonists have gained a reputation of not being the most successful villains, likely because they don't possess the intentions of typical bad guys - and Jessie and James may not actually be truly evil characters.
Jessie and James both have difficult pasts. Jessie's mother, Miyamoto, went missing when she was a child, leaving her in a foster home to grow up in poverty. James was born into wealth but grew up stifled and miserable, as he was expected to inherit and continue his family's legacy. Both joined Pokémon's Team Rocket in an attempt to prove themselves, and they constantly battle for the approval of Team Rocket's leader, Giovanni. It is their goal to show they are both competent and worthy of the praise of their superior, likely as a result of the pair growing up feeling inadequate to their caregivers.
Jessie and James both have a deep sense of loyalty to Team Rocket, specifically to each other and to Meowth. In an absence of supportive families outside of Team Rocket, they appear to have found family in each other, creating a deep bond. While both Jessie and James have had opportunities during the Pokémon series to step away from Team Rocket and leave villainy behind, they both continually turn these chances down, not wanting abandon each other and their found family.
Pokémon's Jessie & James Explore The Effects Of Childhood Neglect
While Jessie, James and Meowth regularly engage in behavior that ranges from annoying to upsetting as they steal Pokémon and create turmoil, they have also been shown to have moments of compassion, not just for Ash and his friends but for people they meet while following him through Pokémon's various regions. In Pokémon XY episode 39, for example, when Ash and his friends are attending a summer camp lead by professor Sycamore, Team Rocket serves as cooks that care for his team. Jessie and James do have a goal to capture rare Pokémon to prove themselves to Giovanni and Team Rocket, but their actions when not attempting to ambush Ash are actually surprisingly thoughtful, creating a dissonance with the idea of Jessie and James being truly evil.
The Pokémon anime has added dimension to Jessie and James as characters that make the audience sympathize with their reasons for being a part of Team Rocket. Their overarching struggles are a heartbreaking example of what happens when children experience trauma and deep feelings of inadequacy. Neither of them set out to be evil or to hurt others, but, in their attempts to show they have value, Jessie and James have taken a negative path in life. Pokémon's Jessie and James wanted nothing more than to show someone they were capable of doing something amazing, and, in the process, they have been extorted for their desire to fit in and have value.