Whose Side Are You On? - 1 Samuel 29

Recently, I was listening to a podcast that reflected on the stories of people who, over time, quietly drifted from the convictions they once held dear. These weren’t necessarily stories of scandal or public failure—but something subtler, and perhaps more unsettling. These were people who once walked closely with the Lord, who once stood with confidence in their faith, but who gradually began to compromise. Not all at once, but little by little. The hosts raised a deeply important question—one that’s worth considering for each of us: What causes someone to drift from what they once knew to be true?

Was it weakness? Were they seduced by influence, power, or the allure of cultural approval? Perhaps they were simply excited to be in the room with important people—politicians, academics, journalists, or thought leaders. And once they were there, they realized that to stay in that room, to keep their seat at the table, they would need to soften their stance, compromise on key truths, or avoid saying hard things. Little by little, what began as an opportunity to speak truth in influential spaces turned into a quiet surrender of the very truths that gave them a platform in the first place.

In 1 Samuel 29, David found himself in a similar place. David wasn’t necessarily looking for a place to influence important people, rather, David was looking for something much more basic: He was looking for peace, comfort, and security.

David didn’t end up preparing to go to war with the Philistines because he rejected his God and his country. Rather it was his fear of Saul that motivated him to seek refuge in Philistia. And the comfort, peace, and ease of life kept him there. And now, all the little compromises he made to have peace and comfort have finally caught up with him because he’s now preparing to march with the Philistine army against the people of Israel – the very people he was anointed to lead.

This passage confronts us with a critical question: Are we faithfully and uncompromisingly marching with the Lord or have we drifted towards making an alliance with the very people who oppose Him? And our passage reminds us of several things: first, God’s people do not belong among His enemies (vv. 1-5), second, God’s grace provides an escape hatch (vv. 6-10), and lastly, we’re reminded that God calls his people home (v. 11).

Last week we looked at what was going on behind Israelite lines. Remember how Saul consulted a medium in order to figure out what to do with the impending war with the Philistines. And through the prophet Samuel who was brought forth from the dead prophesied of Saul’s and Israel’s impending destruction.

God’s people do not belong among His enemies (vv. 1-5)

But now, in chapter 29, we learn of what’s going on behind Philistine lines. They’re preparing for war with Israel, and the Philistines are examining their army and of course, it’s within the ranks of their army they discovered David and his men.

It’s important to remember how David found himself there. In 1 Samuel 27, David fled Israel and went to live among the Philistines in order to escape from Saul. And of course, this put David in a precarious position, because there was an expectation from the Philistine King Achish that he and his men would conduct raids against Israel.

But rather than raiding Israel, David and his men chose to raid the enemies of Israel instead. But when Achish asked David who he had raided he would lie and tell him that he had been raiding various parts of Israel. And so David had to walk a tightrope. On the one hand he didn’t want to do anything to harm the people of Israel, but on the other hand he wanted to keep the Philistines happy.

Needless to say, David had put himself and the men who were with him in a tremendous bind by forming an alliance with the Philistines and now things are coming to a head. Will David and his men actually fight for the Philistines against the people of Israel?

But of course, we know what happens. Ultimately, they don’t because the Philistine commanders noticed David and his small army of Hebrews among the Philistine ranks. And so they asked King Achish in verse 2, “What are these Hebrews doing here?”

Obviously, they were concerned about having a band of Jewish men among their ranks. But King Achish wasn’t worried about David and his men – he defended David to his commanders in verse 3, “Is this not David, the servant of Saul, king of Israel, who has been with me now for days and years, and since he deserted to me I have found no fault in him to this day.”

The vast majority of chapter 29 is devoted to Achish defending David and his men. But the commanders of the Philistine army saw David and his men as a tremendous liability in war. They make the point that David could reconcile himself to Saul and Israel “with the heads of the men here.”

They weren’t necessarily wrong, were they? And in raising their concerns, they expose the deeper issue at play—why is David in Philistia at all? David didn’t belong there. He never should have never been in that position where there would even be a chance that he might have to march with the enemies of God’s people.

Regardless of how we might explain his motives—whether it was fear, a survival instinct, or strategic calculation—it still adds up to this: David made compromises with those who stood in opposition to God’s people.

We might look at what’s going on here with David and think, how could he possibly do that? But the truth is, it could happen to us as well. Sometimes, intentionally or passively, we align ourselves with the systems, values, and practices of the very people who stand in opposition to God. It’s the sort of thing that I was talking about earlier! We’re often seduced by our desire to be liked, or welcomed into certain social circles and in order to keep the door open for opportunities, or keep the paycheck, or maintain the relationships we have to either be silent or downplay our Christian convictions.

It’s easy to rationalize our silence or willingness to downplay our Christian convictions if it’s what’s necessary for keeping the peace or maintaining a certain level of comfort. But if you’re not careful, you can easily find yourself making unconscious alliances with the enemies of God.

The truth is, God’s people do not belong among His enemies regardless of the perceived perks! Remember what the Lord Jesus Christ said in Matthew 12, “Whoever is not with me is against me…”

It’s so easy to convince ourselves that there is some sort of middle ground. That there’s a tightrope we’re more than capable of walking where we’ll keep people who detest the things of God happy by remaining silent on our Biblical convictions in order to avoid confrontation or preserve our own comfort without ever turning our back on the Lord. But Jesus makes it clear: there is no middle ground. There is no neutrality in the kingdom of God. You are either with Him or against Him.

I’m certainly not suggesting that you bring up Christian convictions simply to offend those around you. I hope no one is hearing that. Rather, what I’m talking about is those times – and we’ve all experienced them – where we were backed into a corner of either remaining silent or downplaying our Biblical convictions in order to get something that we want.

And that’s what makes compromise so dangerous. It doesn’t feel like rebellion. It feels reasonable. It feels prudent. It’s even easy to convince yourself you’re being wise. But over time, those small concessions begin to shape your identity, your loyalties, and your direction. Before you know it, you’re marching with the Philistines, making plans with people who oppose the very gospel you claim to love and believe.

God’s grace provides an escape hatch (vv. 6-10)

One of the more interesting details about 1 Samuel 29 is that outside of a passing reference to the Lord by Achish, the name of the Lord isn’t mentioned. And yet, we can see the Lord’s hand all over the circumstances and details of this passage.

Last week, when Saul met with a medium and brought Samuel forth from the dead – Samuel told Saul that the kingdom of Israel was going to be ripped from him and given to David. Here, in chapter 29, the name of the Lord isn’t necessarily mentioned, but we can see his hand of providence all over the place, can’t we? He’s moving all the chess pieces into position to fulfill his Word – that David would be king in Israel.

And we see things coming together for David in verses 6-10, when it was determined that David and his men were not going to be allowed to march with the Philistines. They were too much of a liability. But amazingly, King Achish felt bad. He told David in verses 6-7 that,

“As the Lord lives, you have been honest, and to me it seems right that you should march out and in with me in the campaign. For I have found nothing wrong in you from the day of your coming to me to this day. Nevertheless, the lords do not approve of you. 7 So go back now; and go peaceably, that you may not displease the lords of the Philistines.”

Achish explained to David that he didn’t understand the Philistine lords’ insistence that David and his men not fight for them. From his perspective, David had done everything he’d ever asked of him. He trusted David. He even said in verse 9 that David was as blameless as an angel of God. But of course, the decision was out of his hands.

David was able to walk away from marching with the Philistines with his relationship with Achish still intact. In fact, Achish really liked David. Which is important, right? It’s good for unbelievers to respect and think well of you. Scripture tells us in places like 1 Peter 2:12 to keep our conduct honorable among outsiders. However, David had not been as honest with Achish as he thought. He had not been raiding Israel as he claimed—he had been attacking the enemies of Israel. David would not be able to keep the charade going indefinitely, eventually someone was going to figure it out and his house of cards was going to come crumbling down.

Even when Achish broke the news to David, he asked in verse 8,

“But what have I done? What have you found in your servant from the day I entered your service until now, that I may not go and fight against the enemies of my lord the king?”

David’s protest was a lot of words, but he wasn’t eager to fight against the people of Israel. After all, he had been raiding the enemies of Israel for years at this point! He simply didn’t want to blow his cover. The fact that the Philistine lords sent David and his men out from their ranks ultimately helped David.

And so what’s absolutely crystal clear from this passage is that God’s gracious hand of providence is upon David! David was able to avoid a terrible crisis without destroying his relationship with Israel or blowing his cover to the Philistines. David would have never been able to be king in Israel had he marched with the Philistines against the people of Israel.

Which is the way it normally works, isn’t it? How many times have you looked back at different situations in your life and thought, I dodged a bullet right there. That situation could have destroyed my career, my family, my reputation—but for whatever reason, the way things played out, I came out completely unscathed. God protected me through that whole ordeal and I didn’t even see it at the time!

In fact, sometimes the Lord saves us from ourselves! We put ourselves in these terrible situations that we never should’ve been in—out of fear, desperation, pride, or compromise. And yet, in His mercy, God intervenes. Not because we deserve it. Not because we did everything right. But because He is gracious, merciful, slow to anger and abounding in steadfast love.

In our passage, God graciously removed David from a no-win situation that David’s sin had created.

Which by the way, is a reflection of the gospel, isn’t it? He saves us not because of anything that we have done, not because of any inherent righteousness, but because of His grace.

Christ didn’t come to save those who had it all together, but for the lost, the broken, the fearful, the compromised. He bore our sin, our failures, our shame; and in exchange, gave us His righteousness. In Christ, we see the fullness of God’s grace and mercy on display.

God calls his people home (v. 11)

David’s fears and desire for peace and security led him to take up residence with the Philistines. And before he knew it, he was getting ready to go to war against his very own people. It’s rather shocking how he got there through a series of small incremental steps.

The words from this morning’s confession of sin ring so true don’t they? “...we have erred and strayed from your ways like lost sheep, we have followed too much the devices and desires of our own hearts…” Who cannot relate to those words? Who hasn’t felt like they’ve strayed from the Lord like a lost sheep?

God, in His mercy steps in—sometimes through circumstances we didn’t ask for and don’t understand—and gently puts us back on the right path. David was sent home by the very people he had tried to blend in with. The rejection of the Philistine commanders wasn’t a punishment; it was God’s mercy in disguise. David didn’t belong with them and deep down, he probably knew it.

But isn’t it true that the things that cause us to stray aren’t necessarily bad things in and of themselves? Most people don’t wake up and say, “I’m done with God. It’s time to chase after what will destroy me.” Very few set out intentionally to wreck their spiritual lives. What’s far more common is a small compromise—one that feels reasonable in the moment. We might say, “I just need a break,” or “This feels safer, more stable,” or “Surely God will understand.”

That’s exactly what David did. He was exhausted. He had spent years on the run from Saul. And in a moment of weariness and self-preservation, he chose to seek refuge among the Philistines. Was it outright rebellion? Not exactly. But it was a decision rooted in fear rather than faith. A small step off course, which slowly led him into enemy territory—literally and spiritually.

But the Lord had other plans. God had not abandoned David—He was preserving him. In 1 Samuel 29:11, we read: “David set out with his men early in the morning to return to the land of the Philistines. But the Philistines went up to Jezreel.” Jezreel was the battlefield, the place where Saul’s kingdom would meet its tragic end. But David was sent away—back to Ziklag. He didn’t even realize it, but God was pulling him out of the fight, sending him away from compromise, and setting him back on the path to the throne.

It’s a quiet but powerful moment of divine intervention. And did you notice the subtle contrast the writer includes? All the twisted and dark things Saul did in chapter 28 took place in the middle of the night—under the cover of darkness, in secrecy, in desperation. But David is sent back to Ziklag “early in the morning.” There’s symbolism here. As the sun rose, so did God’s purposes for David begin to dawn again.

From the ashes of Ziklag, David would rise. Which is exactly the way God operates! He takes us from the ashes of our own failures and raises His people. Even when we stray, even when we settle in the wrong places, God is faithful to His Word and merciful to His children. Like David, we may not see it in the moment, but God’s hand will guide us home.

God has a unique way of drawing His people home, doesn’t He?

He’s the good Father from the prodigal son, receiving his lost son with open arms. He’s the Savior who leaves the ninety-nine to retrieve the one lost sheep.

So let me ask you plainly: Whose side are you on? Where are you today? Are you walking faithfully with the Lord, or have you slowly, maybe even subtly, aligned yourself with the very forces that stand opposed to Him? This passage doesn’t just recount a historical episode from David’s life—it holds up a mirror to our hearts. Because like David, we too can find ourselves in places we never imagined, aligned with people and priorities that have no business shaping the life of a child of God.

You may not have set out to rebel. Maybe it was just one small decision. Maybe, like David, you were tired—tired of the fight, tired of waiting, tired of the uncertainty. So you made a choice that seemed reasonable in the moment. But now you find yourself far from where you’re supposed to be. Perhaps your joy is gone. Your spiritual hunger has dulled. You feel like a stranger in enemy territory.

If you’ve wandered from the Lord because of foolish decisions you’ve made, there is still hope. The grace that led David from behind enemy lines is the same grace that will meet you exactly where you are. The cross of Jesus Christ is proof that God doesn’t abandon His people—even when they’ve stumbled into places they never should’ve been.

We clearly see God’s grace in this passage and are reminded that God doesn't leave His children where they don’t belong. God’s people were never meant to blend in with His enemies. David may have thought he found safety in Philistine territory, but it was never home. And the same is true for us. The world may offer comfort, convenience, or a false sense of peace, but we’re never at home in enemy territory.

Have you wandered away? Have you drifted? Then it’s time for you to come home.

Amen. Let’s pray together.