9. Bail Organa
Another possible cameo from a prequel character, Bail Organa was a member of the Republic Senate during the prequel trilogy, hailing from the planet Alderaan.
A friend of the Jedi, Organa helped both Kenobi and Yoda to escape into hiding following Order 66 during Revenge of the Sith, and afterward, offered to adopt baby Leia following the death of Padme, promising to raise her as his daughter and protect her from the Empire.
Naturally, the character of Bail Organa would fit in nicely to a flashback during Obi-Wan’s days as a Jedi. But beyond that, he could reasonably fit into his story during Kenobi’s time in hiding.
Organa was one of the few people who knew that Obi-Wan intended to go into hiding on Tatooine and watch over Luke as he grew up. So if any character was to head to the desert planet to find him, it would be Bail.
Additionally, having him appear during the show’s timeline on Alderaan could also provide an opportunity for a young Princess Leia to make an appearance.
The actor who portrayed him, Jimmy Smits, even reprised this role recently in 2016’s Rogue One: A Star Wars Story in a minor role, showing his willingness to return to the Star Wars franchise.
An appearance by Organa may be a little out of left field. But with the right story, an appearance by him certainly would work.