This ones a tough one.
I’m struggling theres so many of them!
I think Judas Iscariot was a poor fellow. In truth he may have been among Jesus (naabi Issaa’s Ru Allah’s) most villified friends. In fact Judas lived to fight the Romans and even recorded his own gospel.
Some say Judas betrayed Jesus. Both it’s hard to pin this down becuase the real tratiors were the entire Sanhedrin. I reckon poor old Pontius pilate had it bad too.
Then again Ikramah bin Abu Jahil died in the way of Islam and was shaheed at Yarmuk with 400 men like the Spartans who did not retreat in the face of over 100,000 byzantine Romans. For the son of Abu Jahil to have died so couragesly is certainly a worthy case.
Oh and although i hated Ayotollah Khomeni of Iran in my formative years. I cannot forget his Fatwa against Salman Rushdie (dajaal, Kaffir) and that made him a hero for me and ultimately i believe Allah might well forgive him for defending the honour of the Phrophet Muhammad Rasoolalah 
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despite his crimes Khomeni the original Darth Vader may have the last laugh as he goes into heaven before Saddam!