When Trypho murdered his brother Jonathan, Simon, the last surviving son of Mattathias, took command. He was the eldest of the five brothers and the only one still alive. Josephus records that the people of Jerusalem welcomed him with wild enthusiasm. Simon stood before the assembly and reminded them of everything his family had sacrificed: "My brothers have all perished for the sake of the laws and the worship of God. I am the only one left. And I will not spare myself in any time of danger."

Trypho had been holding Jonathan as a hostage, promising to release him in exchange for a hundred talents of silver and Jonathan's two sons as hostages. Simon paid the ransom, knowing Trypho would never keep his word. He was right. Trypho took the money and the children, then killed Jonathan anyway. Simon recovered his brother's body and buried him at Modin, building a grand monument over the family tomb with seven marble pyramids, one for each parent and each of the five brothers.

Simon then allied with Antiochus VII, the new Seleucid claimant, against Trypho. Together they drove Trypho from fortress to fortress until he was captured and killed. But Antiochus proved as treacherous as every other Seleucid king. Once Trypho was gone, he turned on Simon and sent his general Cendebeus to ravage Judea. Though Simon was now old, Josephus writes that he fought like a young man, setting ambushes in mountain passes and routing Antiochus's forces in every engagement.

Simon's greatest achievement was not military but political. He negotiated full independence from the Seleucid Empire. The yoke of foreign tribute that had weighed on the Jewish people for 170 years was finally lifted. The people were so grateful that in their contracts and official records they wrote: "In the first year of Simon, benefactor and ethnarch of the Jews." He also conquered Gazara, Joppa, and Jamnia, and captured the hated Seleucid citadel in Jerusalem, demolishing it and leveling the entire hill it stood on so the Temple would tower over every other structure in the city. That demolition took three years of nonstop labor.

Simon ruled for eight years before treachery found him too. His own son-in-law, Ptolemy, ambushed him at a banquet, murdered Simon and two of his sons, and seized Simon's wife. But a third son, John Hyrcanus, escaped. He would carry the Hasmonean dynasty forward into its most powerful era.