I think this one is definitely up @Deacon Ray 's alley. Demetrius I Soter AR drachm (minted circa 152-151 BCE) Apparently he was a real biblical villain. I'll let the Bible describe his transgressions: 1 Maccabees, Chapter 1, Verses 10 through 15 From them came forth a sinful root, Antiochus Epiphanes, son of Antiochus the king; he had been a hostage in Rome. He began to reign in the one hundred and thirty-seventh year of the kingdom of the Greeks. In those days lawless men came forth from Israel, and misled many, saying, "Let us go and make a covenant with the Gentiles round about us, for since we separated from them many evils have come upon us."  This proposal pleased them,  and some of the people eagerly went to the king. He authorized them to observe the ordinances of the Gentiles.  So they built a gymnasium in Jerusalem, according to Gentile custom,  and removed the marks of circumcision, and abandoned the holy covenant. They joined with the Gentiles and sold themselves to do evil. Letting your followers build a Greek style gymnasium (picture naked uncircumcised Greek men) in the heart of the Holy City and recruiting Jewish youth to the ways of the Greeks was definitely not a way to endear yourself in the heart of your Jewish allies/neighbors. Bad move for Demetrius I But then things got worse, he pillaged the Sacred Temple and stole some of the most sacred objects of the ancient Jewish faith. 1 Maccabees, Chapter 1, Verses 21 through 28  He arrogantly entered the sanctuary and took the golden altar, the lampstand for the light, and all its utensils.  He took also the table for the bread of the Presence, the cups for drink offerings, the bowls, the golden censers, the curtain, the crowns, and the gold decoration on the front of the temple; he stripped it all off.  He took the silver and the gold, and the costly vessels; he took also the hidden treasures which he found.  Taking them all, he departed to his own land. He committed deeds of murder, and spoke with great arrogance.  Israel mourned deeply in every community,  rulers and elders groaned, maidens and young men became faint, the beauty of women faded.  Every bridegroom took up the lament; she who sat in the bridal chamber was mourning.  Even the land shook for its inhabitants, and all the house of Jacob was clothed with shame. So yeah, he really ticked off Israel and the Jewish people eventually killed him for it...but at least he is now immortal thanks to the Bible's description of his wikedness. And the man had some cool coinage too.