Sith Obi-Wan AU
Sith typically Fall due to their anger, their hatred, their fear, even their grief, but Obi-Wan was far too good a Jedi to allow himself to succumb to such things.
No, what corrupted Obi-Wan was his derision.
He knew how to handle injustice and tragedy. He’d lived through so many of each that it was second nature to work through and release such damaging emotions. He was, after all, a paragon of the Jedi Order.
But Obi-Wan had his vices. He excelled in manipulation and had perfected the art of mockery. Nine times out of ten he was the smartest person in any room, and he knew it. Sometimes his opponents were so incompetent that it was... amusing. They were so easily led by the nose, danced on strings of lies woven by his silver tongue as if they wanted to be his puppets. As if everything in this galaxy existed to entertain him.
Physical battles were one thing (though he rarely lost those, either), but every battle of wits was a foregone conclusion. Surely it wouldn’t hurt anyone if he dragged his negotiations and trickery out occasionally, just for fun. No one would mind if he played with his food a little before swallowing it whole.
If the games he played with himself using people as pawns lasted a little longer each time, grew just a bit more elaborate, ended with a tad more cruelty, his amusement becoming more condescending each time, it hardly mattered. After all, he always won; his enjoyment hinged entirely on watching what his prey did as it blundered ever closer to his snare. Sometimes they even managed to surprise him. He liked those playthings best; he always rewarded them with his greatest care and attention to detail when deciding how exactly they would lose.
And then one day, he saw the Chancellor up close for the first time since Naboo, and with a spark of interest realized that he wasn’t looking at one more dejarik piece, but another player. One he’d been playing against all along, without ever fully realizing.
Another man might have rankled at this realization. His former padawan certainly would have. (And his predictability--the predictability of everyone, really--was growing tiresome.)
Palpatine met his evaluating gaze, and for a moment there was an undeniable sense of recognition in his eyes, of acknowledgement.
Obi-Wan only felt intrigued at the thought of an equal opponent. This was a game he might actually lose.
How exciting.