Godliness doesn’t always guarantee godly discernment. It’s possible for Christians—even those who are spiritually mature—to make dumb decisions, bad friends, and foolish alliances. But the fact that those things happen doesn’t make them any easier to comprehend.

I’m referring to people who have solid track records of faithful Christian witness but foster associations that are inconsistent with the testimony of their lives. Such paradoxical behavior—and its frequently ruinous outcome—is puzzling to say the least. But there are powerful lessons we need to learn from the fallout—as in the story of Israel’s beloved King Jehoshaphat.

Jehoshaphat ruled over Israel’s Southern Kingdom, Judah, and was one of their godliest kings. He abandoned idolatry and sought the Lord (2 Chronicles 17:3–6), and led Israel to do likewise (2 Chronicles 17:7–9). His reforms garnered great favor and blessing from God—so much so that the “dread of the Lord” fell on all the surrounding pagan nations so that none dared go to war against Jehoshaphat (2 Chronicles 17:10).

Jehoshaphat’s reign was a rare period of God’s favor, in contrast to the spiritual darkness, military tension, and political instability that usually plagued Israel. His rule was a time of extended peace, military strength, material prosperity, and intense instruction of the people in God’s law (2 Chronicles 17:9–18).

Unlike the Southern Kingdom, the Northern Kingdom was ruled by the wicked Ahab, who was heavily influenced by his evil and seductive wife, Jezebel (1 Kings 16:30–33; 21:25). She was a power-hungry psychopath who was more than willing to arrange the deaths of people who stood in the way of getting what she and Ahab wanted (1 Kings 21:1–16). Jezebel’s name is so synonymous with wickedness that it is later ascribed to a debauched deceiver of the Christian church (Revelation 2:20–21), and to this day it remains a potent pejorative.

So why would a godly man want to partner with wicked people like Ahab or Jezebel? Scripture doesn’t offer a clear answer. It merely says that’s exactly what happened—the righteous Jehoshaphat made a marriage alliance with the wicked Ahab (2 Chronicles 18:1). Marriage alliances were often used in the ancient world to safeguard the peace between two nations through marriage between members of each royal family.

But that bizarre coalition with his wicked neighbor didn’t signify Jehoshaphat’s crossing over to the dark side. He continued to conduct himself in a righteous manner even after his foolish alliance with Ahab (2 Chronicles 19:4–11). What we are left to conclude, then, is that Jehoshaphat was not acting out of rebellion or wickedness, but naiveté.

Scripture does record one prophetic rebuke of Jehoshaphat for helping the wicked (2 Chronicles 19:2), but it’s essentially a footnote in a narrative that continues to applaud him. The brevity of that correction, however, is not a sign that the Jehoshaphat-Ahab association was no big deal. Admittedly, there were no immediate repercussions in Jehoshaphat’s life. But Jehoshaphat’s naiveté nonetheless produced devastating consequences.

The alliance between Jehoshaphat and Ahab was forged by the marriage of Jehoshaphat’s heir, Jehoram, to the daughter of Ahab and Jezebel, Athaliah (2 Chronicles 21:6; 22:2–3). Athaliah was clearly well schooled in the wickedness of her parents and brought that heritage as a dominant influence into Jehoshaphat’s house (2 Chronicles 21:5–6). Jehoshaphat didn’t live to see the consequences, but Athaliah’s entry into his family instigated a murderous trail that decimated his male descendants.

When Jehoram ascended the throne after Jehoshaphat’s death, Athaliah clearly had his ear. Jehoram had his six brothers murdered. When Jehoram died, Ahaziah, son of Jehoram and Athaliah, took the throne. As in Jehoram’s reign, Ahaziah’s wickedness was directly attributed to Athaliah’s role as his counselor (2 Chronicles 22:3). When Ahaziah died, Athaliah assassinated all of her grandchildren (except for one infant who was hidden) so that she could rule Judah on her own (2 Chronicles 22:10–12). All that horrific bloodshed was the direct result of Jehoshaphat’s naiveté.

And that naiveté was the result of not applying his good theology (2 Chronicles 17:3–4) when it came to his associations.

It would seem that many Christians today are afflicted with the same blind spot. We see Jehoshaphat’s error repeated continually in the evangelical world: every time a good theologian endorses a book with overtly bad theology, signs onto a statement that contradicts his biblical teaching, or shares the stage with a prosperity heretic. The church hasn’t learned anything from Jehoshaphat’s naiveté—if anything, believers seem determined to repeat his grave mistake, as they continue to forge bad friendships with the world and with false teachers.

There is no shortage of Christians whose love for others includes a naive tolerance of the Athaliahs in their homes and churches. Because they don’t directly feel the danger, they carry on as if there is no danger for anyone else—allowing evil influences to gain a foothold in their families and among their fellow believers.

But we need to heed the apostle Paul’s counsel and recognize our responsibilities as not only advocates for God’s truth but guardians of it as well.

Do not be bound together with unbelievers; for what partnership have righteousness and lawlessness, or what fellowship has light with darkness? Or what harmony has Christ with Belial, or what has a believer in common with an unbeliever? Or what agreement has the temple of God with idols? For we are the temple of the living God; just as God said, “I will dwell in them and walk among them; and I will be their God, and they shall be my people. Therefore, come out from their midst and be separate,” says the Lord. “And do not touch what is unclean.” (2 Corinthians 6:14–17)

In particular, from a parenting perspective, we need to be wise gatekeepers of our homes. That will invariably involve stopping threats at the gate. No matter how well we’ve instructed our children in righteousness, those lessons can be undone if we allow unrighteous influences to vie for their attention and affection. We must maintain a healthy hostility for any invasion of false doctrine—whether through social media, the Internet, bad friendships, or education with an anti-Christian agenda. Jehoshaphat didn’t become an unbeliever, but he allowed unbelief to take root and flourish right under his nose.

I’m not suggesting a legalistic and isolationist approach to parenting. But I am saying that pacifism and poor discernment have no place in our parenting. We must take an active interest and involvement in our children’s lives.

The tragedy of Jehoshaphat is that he was a righteous man who made a naive friendship that ended up destroying his family. But his story lives on in Scripture, reminding us to avoid the same devilish trap.