Chutzpuh pt 2: Losing to Win

Intro: Is Chutzpah really Holy?

For better or for worse, Korean churches tend to be heavily revivalistic. Just about every Korean church that I know of tends to have at least 2 or 3 revivals or revivalistic retreats per year.  And what that meant for me was that early on, I got multiple chances to preach for other church congregations (usually youth groups) besides my own.

One of those times, after teaching on Holy Chutzpah, one of the small group leaders came up to me and explained that one of the kids in the group seemed to misunderstand Chutzpah as ‘lying that God is ok with’. And it made sense why he would think that. In examples that I gave, the Bible seems to condone and even commend people for deception (eg, the midwives in Exodus 1).

The short answer to that is no He doesn’t. God commends faith (or faithfulness) to Him and His Kingdom. And sometimes faith takes shrewd wisdom, especially if you are in a particularly tough or dangerous situations, in order to exercise or execute well.

Chutzpah in the Parable of the Dishonest Manager

The longer answer is found in Luke 16, with the Parable of the dishonest manager, which I am arguing cannot be understood without understanding the concept of (Holy) Chutzpah.

In the parable, there is a master who had a servant/slave whom he was going to fire for grossly mismanaging his wealth. But before the manager was fired, he comes up with this crazy and audacious scheme (chutzpah) to find the master’s debtors, who might have been somewhat wealthy themselves, and slash their debts by as much as half. The idea was that the servant could avoid destitution or hard manual labor by cozying up with these clients who might allow him entrance into their own houses, perhaps even with a position of privilege.

When the wealthy master (who might be a crook himself) finds out, he commends the manager that Jesus Himself characterizes as dishonest.

The key to grasping the parable is understanding that Master is not praising the dishonest manager for his criminal embezzlement. Instead, he is praising him for his shrewdness, probably right before he fires his dishonest butt.

All the commentaries I’ve read on this parable point out that Jesus is not condoning embezzlement or dishonesty. He is contrasting how people of “the world”, who are already ruled by “mammon” show shrewdness that is indicative of its own worldly wisdom, whereas the “Children of Light” too often seem to be lacking in its counterpart, i.e., shrewd wisdom from above.

Furthermore, the very next verse after the parable reads as follows:

“10 One who is faithful in a very little is also faithful in much, and one who is dishonest in a very little is also dishonest in much.”

Thus when you link the parable with the very next paragraph beginning with vs 10, it becomes even more clear that ‘being faithful’ sometimes requires not dishonesty…but shrewd wisdom.

To put it another way, sometimes faith requires some wise chutzpah. This dishonest manager, who is a “son of this world” came up with and brilliantly executed a clever (albeit criminal) plan reminiscent of the cleverness we saw in the midwives of Exodus 1. This audacious cleverness (i.e., chutzpah) is what Jesus laments as lacking in the children of light.

What should this look like in the daily life of a Christian?

So to recap: For Christians, chutzpah isn’t merely some audacious way to deceive people and advance your selfish agenda. The Chutzpah of the Bible most basically teaches us that when oppressed, the bottom of the barrel can contend with the oppressive top, and win. In this way, it’s a powerful coping strategy where one uses shrewd wisdom to overcome disenfranchising odds.

But in Christianity, our King is not calling us to be clever per se. Instead, the call is to be faithful/have faith in the one who has already overcome all of our overwhelming odds on our behalf and in turn, gave us a new, chutzpah-filled, way of living that audaciously aims to bless and transform the entire world.  

Take, for example, the Biblical concept of meekness.

James tells us that Godly wisdom is characterized by meekness.

Meekness basically means weakness, or connotes some kind of lack of strength whether that be social or physical.

In a world where there were no police and strength was considered to be essential for your family (or your country)’s survival, meekness was considered a sin.

This helps us understand how radical Jesus’ words were when He contradicted the conventional wisdom of the day and declared that instead of being sinful, the meek were in fact blessed and would one day inherit the earth.

How do you fight against the Romans? You must use meekness instead of violence or might. And the promise is that in doing so, you’ll eventually take over the world

That sounds audaciously silly, right?

But wait, there’s more. In fact, the New Testament is filled with verses that audaciously contradict conventional wisdom:

“Last shall become first.”

“If you want to be first, you must become the servant of all.

“Do not resist an evil man.”

“Repay evil with good.”

“Turn the other cheek.”

And my favorite way to group these and other verses like them is to point out how all of these statements direct us towards a particular species of chutzpah wisdom is something I call ‘losing to win’.

Losing to Win

About 10 years ago now, I became a youth pastor at a Methodist church. How a Presbyterian (jokingly, we consider ourselves to be mortal theological enemies of Methodists!!!) ended up at a UMC church is a funny story that will have to wait for another day.

But to cut to the chase, those first few years at that church were a nightmare for me. Out of the many things that were difficult, the youth group had a High School student (contemporary) praise leader that I clashed with terribly.

After much fighting, I eventually decided to remove this person from his position of leadership. Doing so caused his parents to become so irate they tried to use their influence within the church to get me fired

The senior pastor called me into in his office and I will never forget the words he said to me. He told me that sometimes in order to win, you have to lose.

And when he said that to me, a whole bunch of Biblical themes and verses all cascaded in my head and something “clicked” inside of me.

In a scenario where we are forbidden to use force, violence, or bullying, how are Christians supposed to win? And it was this Methodist pastor whom God used to explain it to me. You win by losing. If there ever was a practical way to apply Holy Chutzpah-type wisdom, this was it.

Here’s what happened after that epiphany.

Instead of getting defensive and retaliating against the kid or his parents, I apologized to both of them and took responsibility for all of it. Instead of arguing over who was right, I chose (with great difficulty) to simply serve and love them.

It wasn’t perfect, and there were some weeks where my efforts at loving were downright pathetic.

But a few strange things happened, one after another.

The first thing was that shortly after I employed this ‘losing to win’ idea, that whole family left the church. The truth about what had happened came out, and drove the whole church to extend to me a large measure of goodwill that I simply did not have before.

2ndly, the youth group took notice about how I handled things coupled with the fact that my anger issues got a lot better. Quite a few students would later tell me that this is what convinced them to trust and give me a chance. The youth group really took off after that.

And lastly, about 7 years after these events, I was guest speaking at another retreat (gosh…what’s up with these Koreans and retreats!! Hehe!). Shortly after I had finished my sermon, that former praise leader walked in. He had heard I was guest speaking at a retreat site and sought me out to talk. He had matured a lot. Gone was the brash and unteachable youth, and instead, stood before me someone way more emotionally balanced and aware. And he drove 2.5 hours to ask my pastoral advice about someone else’s crazy situation that he was trying to minister into.  I was really proud of him. Back in youth group, he had trouble reaching out to people that he didn’t really know. Now he was trying to minister to people who were hurting so badly that I’m not sure that even I would be that willing to get too involved.

Why it works

Someone once asked me if this is merely reverse psychology. I suppose I can see why someone would think that. But that’s not why it works.

Instead, it works because we have a Savior who came to the earth not as God (even though He still was) but as a servant, living the life that we should have lived and dying the death that we should’ve died.

And in 1 Cor 1:30, we are told that He has become for us Wisdom. And in John 19, this Chutzpah-type Wisdom of God was on full display. There, a poor carpenter’s son (so it was thought) stood before the might and power of the Roman government in Pilate. Jesus loses (i.e., Pilate kills Jesus), but by doing so, it is Jesus and not Caesar who wins.


Joe Kim

Joe Kim is the English Ministry pastor at Emmaus Ministries in Bayside, NY. He was born and raised in Levittown, Pa. He has a BA in Music from Toccoa Falls College in Toccoa, Georgia and an MDiv from Westminster Theological Seminary in Philadelphia. He is married to Emii and has a daughter Norah. Joe has been in ministry to various age groups since 2001. He enjoys reading, playing the guitar, eating, sleeping and breathing…in that order.

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