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In my opinion, the best way to connect the classic and newer Star Wars movies is through the Kenobi series. Perhaps something like this could occur:
When Crimson Dawn threatens the Hutt Cartel on Tatooine (and Luke’s hiding place) Kenobi secretly helps Enfys Nest sabotage Maul’s operation and a ship that will eventually maroon Maul on Malachor V (per the Star Wars Rebels series).
In the process, he rescues Qi’ra. Qi’ra is impressed and attracted to Kenobi, the savior Han Solo never became. As the rules of the Jedi High Council are no more, Kenobi seeks to pass on what he has learned. He and Qi’ra become an item, and eventually have a child together.
Meanwhile, Palpatine has also been concerned regarding Maul’s operation, and has sent Thrawn and the Deathtroopers to deal with the Crimson Dawn problem. While Kenobi is away or purposely distracted, imperial forces kill Qi’ra (the now head of Crimson Dawn) and take their child.
In parallel to Kenobi hiding Luke from Vader to someday destroy Palpatine and the Empire, Palpatine then hides the child (Mara) from Kenobi to someday destroy the Rebel Alliance (and later Luke)…..
Believing that both Qi’ra and Mara are dead, Kenobi mournfully returns to hermitage in Tatooine to watch over his last hope, Luke…The rest of the events from Star Wars Rebels series plays out, and Maul is eventually killed by Kenobi…
The events of Episode IV then occur…Kenobi actually knows of Han Solo through Qi’ra, and wants to place him on a better path. Kenobi sets destiny into place by having Han meet Leia by choosing the Falcon as the ship that is to travel to Alderaan…
After Palpatine trains Mara as an assassin (in a similar manner as the Timothy Zahn Trilogy) and he later supposedly dies in Episode VI (and the events of The Mandalorian series), she still confronts Luke years later as instructed. Luke convinces her to abandon the dark side, they put the past behind them, and they eventually become romantically involved.
However, Luke spends too much time dealing with his Jedi Academy and his worrisome nephew, Ben Solo. This causes a rift, they separate, and Mara never tells Luke that she is pregnant.
Years later, Mara becomes aware that Ben Solo has now destroyed Luke’s Jedi Temple and become Kylo Ren. Mara hides her son (Temiri Blagg) on Canto Bight before being tracked down by the Knights of Ren.
Kylo Ren attempts to lure Luke Skywalker into a confrontation using Mara as bait. Luke doesn’t arrive in time, and she is killed (or perceived to be killed).
Despondent, Luke chooses to go into exile after their deaths. Luke leaves the part of the Star Map with Lor San Tekka in the event Leia needs to contact him…Luke never learns that he has a son.
The events of the Star Wars Sequel Trilogy occur.
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