In all seriousness I feel like the common answers I saw of Diogenes (because that was like, his entire shtick) or Socrates (because they killed him for being annoying) are probably better answers but saying its Trotsky on a leftist forum is way funnier.
Jesus during his time managed to piss off a great many people, so he's probably a contender. He would refuse to answer questions straight and would always use parables, and pissed off the Pharisees to no end. He even befriended a tax collector!
Parables are a decent way to overcome the general illiteracy of the time. People have always responded well to Aesop fables. Use symbolic tales parallel to the deeper lesson and all that.
Creating the worlds most colonial religion is definitely a top tier most aggravating move though tbh.
Actually, according to Mark, Jesus spoke in parables in order to hide the true meaning of what he said. 🤷♂️