Luke Skywalker
Like his grandfather, Ben Solo definitely knew how to start a killing spree of Jedi. But While Leia and Han died trying to save Ben, Luke died in battle with his former apprentice.
After begging Luke to train Ben, Leia finally managed to convince Luke to teach her son the ways of the Force and of the Jedi. Luke was apprehensive about this decision, sensing a lot of the same energy in Ben as in his father Anakin. But, still, Luke took Ben under his wing and trained him at his own Jedi temple.
Years later, in a moment of fear, Luke almost killed an adolescent Ben in fear that he would become the next Darth Vader. Ben, feeling betrayed, turned to the Dark Side and swore revenge on Luke.
In Episode VIII, a much older Luke uses the Force, and the final bouts of his remaining energy, to trick Ben during the battle on Crait between the First Order and the Resistance forces. While Luke’s death was a peaceful one, setting himself upon a rock and gazing into the horizon before evaporating into the wind, it was no less heart-wrenching.
The hero and hope for the Jedi, who set the pace for the original Star Wars films, left us twice–once when we believed Ben killed him in battle, and a second time after we learned it all had been a hoax. Talk about playing with emotions.