He’s Probably Still Very Miserable About Satine Kryze

Okay so we know Obi-Wan is already very miserable by the time he’s on Tatooine—he left Anakin for dead on Mustafar, most of his friends have been wiped out, and the Republic has been transformed into a horrifying galactic Empire. He’s going through it! But it’s probably worth noting that Obi-Wan has a little extra grief you might not be familiar with if you haven’t watched Clone Wars coming into the new show.
In the final days of the Clone Wars, Obi-Wan participated in the defense of the neutral planet Mandalore, after a returned Darth Maul (that’s a long, different story, and more on that later!) and his burgeoning crime syndicate staged a coup to overthrow the planet with the help of the rogue Mandalorian traditionalist faction, the Death Watch. Maul, being Maul, double-crossed the Death Watch to take the planet for himself, deposing, and ultimately executing in front of a horrified Obi-Wan, Mandalore’s ruler, Duchess Satine Kryze.
Obi-Wan and Satine knew each other when they were younger, when Obi-Wan and Qui-Gon were tasked with protecting Satine during the Mandalorian Civil War. They had fallen in love, and Obi-Wan very nearly left the Jedi Order to be with her before they ultimately parted ways. They reunited during the Clone Wars after Satine became the leader of a group of neutral systems advocating for peace, but Obi-Wan’s love died in his arms thanks to Maul’s desire for revenge. We know, thanks to this week’s release of the novel Star Wars: Brotherhood, that it’s Satine who gave Obi-Wan the nickname “Ben” some time in the past—so the fact that he adopts that name on Tatooine again means that she and her absence are likely not far from his thoughts.