13. Courage In The Gap - Jonathan's Bold Faith Series

Courage in the Gap – Jonathan’s Bold Faith

May 21, 2025

Dr. Bradford Reaves

Crossway Christian Fellowship

1 Samuel 14

There are moments in life—and in faith—when staying still becomes the greater risk—when the safety of inaction leads to spiritual stagnation, missed opportunity, or even disobedience. But here’s the tension we must wrestle with before we move forward: How do we know when to wait on God—and when to act in faith? That question has echoed across generations. The answers aren’t always easy. But those who’ve walked faithfully before us offer wisdom we’d be wise to remember:

Oswald Chambers: “Trust God, and do the next thing.” Sometimes, obedience doesn’t wait for certainty. It simply does what faith knows to do next.

Dietrich Bonhoeffer: “Action springs not from thought, but from a readiness for responsibility.” Faith doesn’t always wait for clarity—it moves when it hears the call.

Corrie ten Boom: “Never be afraid to trust an unknown future to a known God.” Bold faith doesn’t require full understanding—just full surrender.

A.W. Tozer: “God is looking for people through whom He can do the impossible. What a pity we plan only the things we can do by ourselves.” Fear plans within comfort. Faith moves where only God can sustain.

The Man in the Red Bandana

On September 11, 2001, as smoke and chaos engulfed the South Tower of the World Trade Center, Welles Crowther, 24, faced one of those moments. He was an equities trader by professio —but a trained volunteer firefighter at heart. When the first plane hit, Welles could’ve waited. He could’ve evacuated. But something in him said: “If I don’t move, people will die.” So he grabbed a red bandana—his signature—and ran into the smoke. Survivors recall him calmly guiding them, carrying some down 17+ flights. He didn’t just go in once—he went back again and again, saving at least 18 lives. He died when the tower collapsed—but not before choosing courage over comfort and sacrifice over safety. His family had no idea… until months later, when stories surfaced of “a man in a red bandana” who kept coming back for more.

From Stairwells to Hillsides – 1 Samuel 14

That’s the kind of holy tension we find in 1 Samuel 14. Saul was sitting under a pomegranate tree—paralyzed by fear, clinging to status, watching the situation deteriorate. But Jonathan? Like Welles, he moved. He didn’t wait for perfect odds or permission. He simply said: “It may be that the Lord will work for us, for nothing can hinder the Lord from saving by many or by few.” (v. 6) This chapter isn’t about tactics. It’s about courage under pressure, and the boldness to act when others sit still in fear.

Some of the greatest acts of faith happen in smoky stairwells and uphill climbs. Not when you have clarity, but when you have conviction. Not when you know what God will do, but when you know who He is. So let me ask you: Are you sitting under the pomegranate tree? Or are you picking up your red bandana?

I. Jonathan’s Bold Faith Initiates Action (vv. 1–14)

1 One day Jonathan the son of Saul said to the young man who carried his armor, “Come, let us go over to the Philistine garrison on the other side.” But he did not tell his father. 2 Saul was staying in the outskirts of Gibeah in the pomegranate cave at Migron. The people who were with him were about six hundred men, 3 including Ahijah the son of Ahitub, Ichabod’s brother, son of Phinehas, son of Eli, the priest of the Lord in Shiloh, wearing an ephod. And the people did not know that Jonathan had gone. 4 Within the passes, by which Jonathan sought to go over to the Philistine garrison, there was a rocky crag on the one side and a rocky crag on the other side. The name of the one was Bozez, and the name of the other Seneh. 5 The one crag rose on the north in front of Michmash, and the other on the south in front of Geba. 6 Jonathan said to the young man who carried his armor, “Come, let us go over to the garrison of these uncircumcised. It may be that the Lord will work for us, for nothing can hinder the Lord from saving by many or by few.”

7 And his armor-bearer said to him, “Do all that is in your heart. Do as you wish. Behold, I am with you heart and soul.” 8 Then Jonathan said, “Behold, we will cross over to the men, and we will show ourselves to them. 9 If they say to us, ‘Wait until we come to you,’ then we will stand still in our place, and we will not go up to them. 10 But if they say, ‘Come up to us,’ then we will go up, for the Lord has given them into our hand. And this shall be the sign to us.”