He sent Jonathan the son of Absalom to Joppa, and with him a considerable army: Jonathan was perhaps the brother of Mattathias mentioned in 1Macc 11.70. The city of Joppa had resisted the Jews for a long time. Simon had captured it earlier and stationed soldiers there (1Macc 12.33-34), but here he decided to rid himself of the threat altogether, and sent troops to drive out the citizens. In 1Macc 14.5 this is remembered as one of his great deeds. A considerable army may be rendered “a large number of soldiers.”

He drove out its occupants and remained there: The pronoun he refers to Jonathan. Once Jonathan captured Joppa, Simon had forces stationed safely on the Mediterranean coast and in Jerusalem, ready to meet any movement from the north by Trypho. An attack on either Jerusalem or Joppa could bring on an attack from the rear from the Jews in the other city. Good News Bible has a good model for this sentence.

Quoted with permission from Bullard, Roger A. and Hatton, Howard A. A Handbook on 1-2 Maccabees. (UBS Helps for Translators). New York: UBS, 2011. For this and other handbooks for translators see here.