First Adventures Together
Note: This covers the Pokémon Chronicles episode, which conflicts notably with established Indigo League canon. But I feel it's important to include this information here, because it helps flesh out both characters in believable ways.
Jessie is in training for Team Rocket, and she has already been through several teammates. (Cassidy, a fellow Team Rocket trainee, teases her about this fact in the above screenshot.) She clearly prefers to act as a lone wolf, since she is not able to tolerate slowness or failure in her partners.
So, when Giovanni finally authorizes her instructor to place her with James, Jessie is unsure of him at first, thinking he's going to be another useless partner. Adding a random, insistent talking Meowth to the mix seems like adding insult to injury--Giovanni has little use for the ingratiating little creature, so he saddles Jessie and James with it (much to Jessie's consternation).
However, James seems oddly determined to succeed with Jessie during their military-esque strength and deprivation training, and Jessie is taken aback by his compassion; he gives up part of his own food to feed their new (and very hungry) Meowth, plus helps the Meowth across through the river and up the cliffsides.
(This motivates Jessie to act with similar compassion, though it is given grudgingly.)
Later, the three are trying to cross a rickety, splintered wooden bridge, the only way to get across the river in their path. Jessie boldly leads the way and barely gets herself across, but when James comes along carrying Meowth, the bridge's ropes finally give way underneath him.
James ends up dangling by Meowth's tail as Jessie holds onto Meowth's front paws, barely safe from the swift river below.
But seeing how much pain Meowth is in, James chooses to fall from the bridge into the river rather than further endanger his team. Horrified, all Jessie and Meowth can do is watch him fall.
James ends up in the hospital, heavily bandaged and in critical condition. Though he is out of commission, Jessie and Meowth plan to go ahead with the last Team Rocket training exercise, breaking into a secure Pokémon lab to steal a rare red Snorlax.
But as they wait and watch in the bushes outside the lab, suddenly James appears, still wearing most of his bandages; he has escaped from the hospital to help his team. He reveals he's still wearing his trainee uniform, and declares he's not going to desert the team when they need him.
Thus, the trio, newly reunited, go on into the lab.
They've neared the target when the three fall in a huge trap hole. Much like at the bridge, James begs Jessie to leave him behind to complete the heist, but Jessie refuses; his compassion has rubbed off on her.
Thanks to this perseverance, the three come the closest to completing the exercise, securing them just enough clout to make them ALL full-fledged Team Rocket members at last.
- Jessie is a reckless leader at first, quick to switch tactics, slow to trust.
- James is a careful follower at first, determined to stay the course.
- Jessie has very little compassion, while James has almost too much for his own good.
- Jessie's headstrong leadership and James' stable support balance each other out.
- Their success together proves why Jessie's other partners didn't succeed; she needed someone who was less selfish.