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The answer to your question is quite simple, although not too obvious if you are a fan of only the anime.

Yes, Kojiro (James) does care for Musashi (Jessie). Not only is this shown in very small doses during the anime, but towards the end of the manga, we come to find out that Jessie and James end up quitting Team Rocket, marrying, and starting a life of their own. This also includes Jessie's pregnancy which is not elaborated on, but clearly shown.

Hope this helps :]

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