The Star Wars prequels left behind a somewhat controversial legacy. Much maligned when first premiering, they have, over time, gained Revenge of the Sith, which does a nice job tying everything together.
With the inevitable outcome of the Republic crumbling and the Empire rising, the fall of the Jedi, and Anakin's transformation into Darth Vader, the ending of the prequels was always bound to be bittersweet. Still, there are some characters who actually benefitted from all of this, while some others saw everything they held precious disappear before their eyes.
Loser: Count Dooku/Darth Tyranus
After being the secret big bad behind the events of Attack of the Clones, Count Dooku was quickly dispatched in the opening scenes of Revenge of the Sith. And judging by his look of confusion after Palpatine orders Anakin to kill him, he most definitely wasn't expecting that.
Dooku was, of course, a bad guy, a Sith Lord, and the apprentice of Darth Sidious. Still, it's easy to see that Palpatine merely saw him as cannon fodder, a way to accelerate Anakin's turn to the dark side. And considering Dooku had his own plans to betray Palpatine, which never came into fruition, he was one of the biggest failures in the prequels.
Winner: Boba Fett & The Clones
The Clone Army became one of the most powerful instruments with which Palpatine secured his rise to power. Blindly and unapologetically loyal to the Republic-turned-Empire, the Clones executed Order 66 under Palpatine's commands, thus eliminating the biggest obstacle between the Chancellor and total control of the galaxy.
Meanwhile, Jango Fett's "son," Boba, left the prequels in a strange place. He lost his father during the climactic battle at the end of Attack of the Clones and inherited his Mandalorian armor and ship. Thus, he continues his father's legacy, eventually becoming one of the galaxy's most dangerous bounty hunters.
Loser: The Jedi
As an institution, the Jedi were respected and almost revered throughout the galaxy. Their power and wisdom were well-known, and their place of honor in the Republic's ranks, unchallenged.
Still, their pride blinded them to the poison that was growing, both in the Senate and among their own ranks. Once Order 66 was executed, nearly every Jedi in the galaxy was murdered, thus ending the organization's domain. Only a few survived and were forced into hiding, knowing full-well that Sidious and Vader would hunt them down.
Winner: Breha & Bail Organa
Despite all the chaos that ruled over the galaxy, there were still some bright spots to be found. One of them is the image of Breha and Bail Organa holding a baby Leia in their arms and looking like the happiest and proudest of parents.
Indeed, Bail reveals that he and his wife have long thought of adopting a girl, telling Yoda and Obi-Wan she will be loved. He fulfills his promise, as Leia grows up to become a strong, independent and capable revolutionary. And while Breha and Bail eventually suffer a cruel and untimely fate, they at least got the chance to have a family.
Loser: Jar Jar Binks
One of the most controversial and divisive characters of the prequels, Jar Jar was almost universally hated by audiences when first introduced in The Phantom Menace. His role was greatly reduced in the following films, but he still played a pivotal and ultimately unfortunate role in the rise of the Empire.
His fate after the rise of the Empire is a sad one indeed. Once again exiled because of his actions, Jar Jar is forced to become a street performer, entertaining children while dressed as a clown. He eventually meets and befriends a young boy, Mapo, who he takes as an apprentice. Jar Jar's reputation, like the prequels themselves, has improved over time, especially with the rise of the Darth Jar Jar theory.
Winner: Beru & Owen Lars
Just like the Organas, the Lars couple received a young child to take care of, Luke. The two raise the boy and live a quiet, almost peaceful life in the desert planet of Tatooine. Luke clearly cares for them, even declining Obi-Wan's initial offer to train him as a Jedi, out of a sense of commitment towards his uncle's farm.
Although Beru and Owen also ultimately suffer a cruel fate at the hands of the Imperial Stormtroopers, they play a large and central role in the life of the hero who would ultimately free the galaxy from the Empire. Their legacy is one for the ages.
Loser: Pé Amidala
Starting the prequel trilogy as the young Queen of Naboo, Pe's life was anything but tranquil. Her forbidden love and eventual marriage to Anakin Skywalker would bring her demise, as she quite literally loses her will to live by the end of Revenge of the Sith.
Pé gets to see the crumble of the Republic and the rise of the Empire. Deleted scenes in RotS hint at her early involvement in the movement that would eventually become the Rebel Alliance. However, she never gets to see her children grow, nor her husband's repentance. Even so, she dies believing that Anakin can still be saved, her last words being "There's good in him. I know, I know there's still."
Winner: Darth Vader
While Anakin Skywalker can definitely be seen as one of the biggest losers in the prequel trilogy, his Sith persona, Darth Vader, emerged triumphant. Vader not only became the chief enforcer of the new Galactic Empire, he also, having lost Pé and believing his children dead, lost all connections to his human past. This allowed him to execute the terrible orders of Sidious without much regret or care.
Vader's life in the Empire would be a dark one, full of death and cruelty. His eventual redemption comes at the expense of his life, but it's a small price to pay to atone for his heavy sins. Still, for a considerable amount of time, he lives as the ultimate threat in the galaxy.
Loser: Obi-Wan Kenobi
Obi-Wan lost not only the organization he was loyal to, and the friends and mentors he had within it, he also lost his closest companion, a man he considered not only his brother but his equal. Pé's death, Yoda's exile, and the Skywalker children's fates all left him broken and disillusioned with life.
Having already lost Qui-Gon at the hands of Darth Maul, Obi-Wan was no stranger to tragedy. Still, Anakin's actions and the fate of the galaxy are blows that certainly stay with him in his long, solitary brave warrior.
Winner: Chancellor Palpatine/Darth Sidious
The ultimate winner of the prequels, Supreme Chancellor Palpatine managed to not only bring the Sith out of oblivion but actually put them in control of the galaxy. He also succeeded in turning Anakin to the dark side of the force, getting rid of the Jedi, and establishing himself as the maximum authority of the first Galactic Empire.
For years, he held on to his power, achieving terrible things with the help of his apprentice, Darth Vader. The extent of his victory cannot be stressed enough. Coming after years of planning, he tricked even the most powerful of Jedi into believing his innocence before revealing his true colors. His actions and ultimate victory would almost be irable if they weren't so vile.
