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Today we begin a new book—Judges—buckle up, because it’s a roller coaster ride from start to finish. Israel’s story rides up and down across these 21 chapters, bridging the gap between setting up memorial stones in Joshua, to setting up royal thrones in 1st Samuel—from Theocracy to Monarchy. The first two chapters set the stage for why Israel was made to endure over 400 years on the wild ancient coaster—The Cycle of Chaos. Hold on tight—every man is about to do what is right in his own eyes.

At first, things seem to be moving in a steady positive direction. Early in Judges chapter one, the tribe of Judah finds favor with God as they are commissioned to continue the military campaign of cleansing the land. They seemingly conquering Jerusalem, as we read in verse 8,

“And the men of Judah fought against Jerusalem and captured it and struck it with the edge of the sword and set the city on fire.”

However, the momentum doesn’t last long. By verse 21, we read,

“But the people of Benjamin did not drive out the Jebusites who lived in Jerusalem, so the Jebusites have lived with the people of Benjamin in Jerusalem to this day.”

It’s a head-scratcher, even though Judah initially conquered Jerusalem, the Benjaminites fail to drive the Jebusites out — and so they stuck around. And from the ashes, Jerusalem rose again because of Benjamin's failure to fully obey God’s command.

SIDENOTE: Are you wondering, like I was, why Benjamin had anything to do with Jerusalem? I thought Jerusalem was Judah's. Well geographically, Jerusalem sat in Benjamin close to the border of Judah. When Israel became a monarchy, Jerusalem became the capital of Israel. Later, when the kingdom divided under Rehoboam, Jerusalem remained the capital of the southern kingdom—Judah.

The latter half of Judges chapter one reads like a list of unfinished business: cities were left unconquered, enemies were left in the land, compromises were made. Instead of obeying God’s commands, the Israelites often chose convenience—keeping the Canaanites as forced laborers rather than removing them as God had commanded.

Because of this disobedience, God declared in Judges 2:2–3,

“…you have not obeyed my voice. What is this you have done? So now I say, I will not drive them out before you, but they shall become thorns in your sides, and their gods shall be a snare for you.”

And so, the wild ride begins. It took less than one generation after Joshua’s leadership for the people to turn away from the one true God. The rest of the book becomes a heartbreaking cycle: Israel abandons God, God raises up a judge to rescue them, the people return to God, the judge dies, and the people immediately fall back into wickedness. The root of it all? Disobedience to the Lord.

Takeaway: Obedience to God matters. When we compromise even slightly, we open the door for pain, bondage, and spiritual drift. The good news for us today is that we have access to the Holy Spirit—the very presence of God living within us. He empowers us to walk in obedience, not by our own strength, but by surrendering fully to Him. If we trust and obey, we will experience His freedom, protection, and blessing—even when the world around us feels like a chaotic roller coaster.