Then he crossed over to attack the Ammonites: Ammon was a country just east of the Jordan River, northeast of the Dead Sea. Since we do not know where the Baeanites lived (verses 4-5), we cannot know what Judas crossed over; presumably it was a river, but there is no way of knowing which one. It is possible to avoid the problem by saying “Then he and his soldiers marched against [or, invaded] the land of Ammon.”
Where he found a strong band and many people with Timothy as their leader: Presumably many people refers to the strong band; Good News Bible says “a large and powerful army,” which is a clear and accurate translation. Timothy was either a local Ammonite chief or the commander of Syrian forces in Ammon. This clause may be rendered “where he met a large number of well-armed soldiers commanded by a man named Timothy.”
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.

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