The Judges of Israel were the leaders who succeeded Joshua and Caleb. At times of war they acted as military leaders (Gideon) or individual fighters (Samson). In peacetime they were those who were recognized as having the authority and wisdom to guide the people (Deborah). Many of the problems encountered by the Israelites at this time stemmed from their allowing the Canaanites and others to remain in the land. This led to the incorporation of Canaanite religious rituals and beliefs into the worship of God - this process is known as "syncretism".

The historical period covered by the Book of Judges is probably 1,200-1,020 BC, towards the end of the Late Bronze Age, when iron was just coming into use (Sisera had "chariots of iron" (Judges 4:3). The length of the period could be as long as 400 years, or as short as 100 - it can not be calculated by merely adding together the years that each Judge was active. There were periods between Judges, but also Judges were active in various parts of the land, and some of them may have been contemporaries acting in different regions.

Structure of the Book of Judges :
Judges 1:1-3:8 - Historical setting
Judges 3:9-3:11 - Othniel and the King of Aram
Judges 3:12-3:30 - Ehud and the Moabites
Judges 3:31 - Shamgar and the Philistines
Judges, chapters 4 & 5 - Deborah and Barak against the Jabin and Sisera of Hazor
Judges, chapters 6-8 - Gideon and the Midianites
Judges, chapter 9 - Gideon's illegitimate son Abimelech kills his half-brothers and sets himself up as "king", but is killed when a woman drops a stone on his head.
Judges 10:1-2 - Tolar is Judge in northen Israel
Judges 10:3-5 - Jair is Judge in Gilead, East of the Jordan
Judges 10:6-11:40 - Jephthah and the Ammonites
Judges, chapters 13-16 - Samson and the Philistines
Judges, chapters 17-18 - Micah (not the later prophet) and his mother set up their own shrine for worship, but are overpowered by men from the tribe of Dan. The Danites do not settle in the region given to them by Joshua, but take the most northerly part of what becomes the Land of Israel. They continue to use Micah's idol for worship until the Fall of the Northern Kingdom of Israel to the Assyrians, ca. 722 BC.
Judges, chapter 19 - anarchy and violence amongst the Israelites
Judges, chapters 20-21 - further anarchy and violence. The tribe of Benjamin is almost annihilated.

Judges 1:16 - "the City of Palm Trees" refers to Jericho, built at an oasis where a stream comes out of the cliffs west of the town. The stream still exists, and is one of the sources of water for the modern town of Jericho. The region beyond the oasis is barren and treeless.
Judges 1:19 - "chariots of iron" the coastal peoples had trading contact with the Hittites, who were among the first people to work iron. At this time the Israelites had bronze weapons only.
Judges 1:21 - this must have been written before the time of king David, who took Jerusalem from the Jebusites (II Samuel 5:6-7)
Judges 1:27-2:5 - God had told the Israelites to destroy all traces of the Canaanites, but whether from greed and expediency or from misplaced mercy, the Israelites allowed many of them to live. As a result, the Israelites began to mix with the Canaanites, and picked up some of their religious perversions such as child sacrifice and religious prostitution.
Judges 4:5 - the place where Deborah lived is still a village in northern Israel, called Dabburyah by the Arab population.
Judges 5:16-17 - some of the tribes did not come to the help of Deborah and Barak.
Judges 6:25-32 - a picture of how far Israel had strayed from worship of God - the people not only had built an altar to Baal, the Canaanite storm and fertility god, but wanted to kill Gideon for tearing it down.
Judges 7:5-7 - Those who went down on their knees to drink probably let go of their weapons, and certainly were unable to keep a watch on their surroundings. Those who lapped probably remained standing, and cupped water up in one hand to drink, thus demonstrating their preparedeness for danger.
Judges 8:27 - No-one is sure now what an ephod was, except that it was associated with the high Priest and with the worship of God (Exodus 28:4-29).
Judges 9:45 - "sowed it with salt" means that they ploughed salt into the ground so that plants would not grow well - it would not be possible for anyone to grow good crops for years to come. The Romans did this to Jerusalem after the revolt of AD 70.
Judges 17:1-2 - Micah had stolen the money from his mother, but evidently when he heard her put a curse on it he dared not keep it, but restored it to her.
Judges 17:3-6 - Micah and his mother engaged in practices which God had absolutely forbidden - making graven images for worship, consecrating 'priests' who were not of the Aaronic line, and making an ephod and teraphim (little household gods).
Judges 17:6, 21:25 - verses which summarize the anarchy of the period of the Judges - "everyone did what was right in his own eyes" ie. they did not bother to check out whether or not things were right in God's eyes.