Teaching the Wicked – Good Luck with That!


#27 of a Series on Psalm 50 –  “I will teach transgressors your ways and the wicked shall return to You… .“  (Orthodox Study Bible)

I wonder if other priests have had the following experience.  You give the homily at the Liturgy and on the way back to the altar to do Part 2 of the Liturgy, you ask yourself, ‘Did this mean anything to anybody out there?’ A second question often follows, ‘Was there anything in what I said that was worth listening to?’ In the humorous but pithy saying used by people today, are the faithful thinking to themselves, ‘Well, that’s 20 minutes of my life I’ll never get back!’?

These are not bad questions to ask.  Preachers can notoriously go on and on with zero positive effect (a situation feared by all parishioners) and possibly actually doing harm in the end.  We’ve got to be on guard against that.  A positive effect though can be that our preaching undergoes a better critique – either by myself, or others, who can help us understand why our message doesn’t get through, or perhaps more importantly, why the message isn’t reflecting the Message of Jesus.

One thing that I’ve noticed over the years is an overall aversion in our culture to preaching.  Preaching comes with a point – and people ‘don’t want to be preached to.’   But if that’s the case then Peter would never have stood up and preached in Acts 2 after the coming of the Holy Spirit, and the first 3000 would not have been converted, and nobody after that, and the New Testament would have ended there!  I don’t like to be preached at either.  But I do like to be engaged by a thoughtful preacher who cares, and who has a point worth hearing.  What is usually the case is that the resistance of us, the audience, to the point is often the point.  Why do we resist hearing something new, or challenging, that may in the end better our lives?  The goal of preaching is not just to ‘make points’ nor to slay people with impressive words, but to open the Word in a way that the embrace of divine Love through the Gospel challenges people to discover.  It opens hearts, not closes minds.  If this is the case, then personal sin will always oppose the Gospel, hence repentance is the starting point of the Point.

Opposition Research – What do people respond to?

The Right Words – Truth:  The testimony that leads to conversion is that which is True.  Jesus Christ identified Himself as the Truth.  His words have the power to penetrate the human heart.  The teaching or preaching which is just pious philosophy or a feel-good message will have no lasting spiritual impact.

The Right Person – Authenticity and Authority:  I mention this as a follow-up to a previous reflection.  The message of the Gospel is validated by the words and actions of the person presenting it.  Only a person who has been ‘leveled’ by repentance is believable when repentance is being preached.  It comes across not only through the words, but an inner awareness coupled to emotion and always, humility. It can faked – but not successfully certainly not over the long term.  The authenticity ratchets up when the Way of Christ is visible in other aspects of the life of the local church and its flock, especially the pastor, where, love and service to others is felt, especially the poor and others on the fringes. This means the message may be taught by words but is affirmed through the works of those living it. 

The experience of true humility (for the repentant) as well as that manifest in the life of Christ who needed no repentance, leant an air of authority to Christ and the apostles who preached in his name. The people contrasted that authenticity of Christ with the Pharisees and scribes, saying, “He speaks with authority.” (Mt. 7:29)  The repentant need not fear accusations because they’ve already dealt with their sins.  The accusers (in imitation of the Devil) have no power over the Truth within them of God’s mercy, despite their sin. 

A Crack and an Opening:  For the Word to penetrate our consciousness requires something special to happen. This is God’s work taking place long before a preacher/teacher shows up.  We learn from the story of Nathaniel’s conversion (Jn 1) that something had happened in his life while he was under the fig tree, that prepared him to hear the words of Jesus reference that event. It really isn’t important to us here what that was, otherwise the narrative would include it.  But it predisposed Nathaniel to hear the words of Truth of Jesus when He said, “I saw you under the fig tree.” And that was enough to allow a flood of awareness to come to Nathaniel, leading him to cry out, “You are the Son of God! You are the King of Israel.”    SOMETHING happened under the fig tree that served as the trigger to his awareness.[i]  Scripture is replete with stories[ii]  of events small or large that serve as the gateway to a person discovering the Lord’s Word and call in their lives.  For the shepherds at Bethlehem it was the appearance of angels and a message of a birth of a child in nearby Bethlehem. The healings and miracles of Jesus and the apostles often served to open this awareness in the minds of people.  

For us that moment can be anything – a chance encounter with another person, a freak seemingly accidental event,  or an event that pricks our conscience with a memory, a moment of sheer grace and joy[iii],  or simply hitting rock bottom in habitual sin in the moment that says, ‘This is now or never.’  The stories of each person’s preparation by God to meet Him through the encounter is distinct and personal.  But it’s important at some point that there be a teacher, to help explain, encourage and ultimately make a disciple (beginning with sacramental initiation but not ending there[iv]) of the person who allows God’s truth to enter their souls. So Paul needed Ananias (whom God had prepared beforehand) to teach him the most basic truths of Christ and the Christian way, heal him of his blindness, and baptize him.  Cornelius, despite his virtuous life, needed Peter to explain the gospel to him

But even as in the days of Christ, when miracles are revealed, some people never truly open their hearts to Him – nothing really happens in that case.  The nine lepers are healed, but only one gets healed spiritually by returning to Jesus and falling on his knees.  This is why Jesus exhorted his disciples in their ministry to ‘shake the dust from their feet’ (Mt. 10:14) as they left the towns that rejected the gospel.  This, I believe was for two reasons.  First, as a sign that the hour of mercy will end and a ‘last chance’ for people to see how serious these spiritual matters are, and the time to repent is literally fleeing.  The second is for the sake of the disciples themselves, because the continuous opposition would (as they were just beginning at least) be a great discouragement.


The conversion experience, if authentic, always carries two powerful elements.  While seemingly the call to repentance experienced through guilt and sorrow is the trigger, what’s most important ultimately is the experience of the mercy and compassion of Jesus in forgiving our sins.  The teacher/preacher of the Gospel needs to bring forward both.  If the message of mercy is absent, then the message is demoralizing, and false or misleading, because God came into the world not to condemn sinners, but that the world might believe through Christ. (Jn. 3:17)  If compassion is missing, then all that is heard from the preaching or teaching is judgment, condemnation, and darkness.  The ‘hell’s fire and brimstone preaching when limited in this way can be effective in instilling fear into people,[v] but does not open the heart to grace without the saving assurance of God’s forgiveness.  The effective teacher of the Word is always compassionate. The Prophet Nathan’s testimony to David was ultimately an act of compassion.


When repentance happens and God’s mercy is experienced, the natural fruit of this is joy and thanksgiving.  I had mentioned joy in a previous reflection and we’ll take a look at thanksgiving in a future chapter.

Who are we teaching?

Jesus made a big deal about the audiences he preached to.  He was pretty much unsuccessful calling the Pharisees, Sadducees, scribes and religious leaders of his day to His message of salvation.  Yet he went to them, because they were sinners and a few, like Nicodemus and Joseph of Arimathea got the message.  Everybody got their chance. But he was quite clear to the apostles as to who the audience was that would most likely hear and respond to His message.  It was the public sinners like tax collectors Zacchaeus and Matthew and their buddies with whom Jesus would sit and eat.  The prostitutes, the lepers, the Samaritans and others excluded from the society – and the marginalized poor and suffering were the ones where the seed of the gospel would find fertile soil.  And, as the Orthodox Church reads on the Second Sunday Before Christmas, when those who were initially called would reject Him and His message, the Master would dispatch his disciples ‘to the highways and byways’ to bring in those for whom the Banquet would be set, meaning the Gentiles, and that includes us. (Lk. 14:15-24)

Real Preaching – Tough Sledding

There’s an old saying, ‘That’s easyYou’re preaching to the choir.’  This refers to someone speaking to an audience that’s already on his side and understands the message, just as typically the choir in a church setting would already be believers in the Christian message.  But preaching to people who are not the choir is not easy.  It means going outside of one’s comfort zone of awareness to people who may live and think very differently than we do. That includes those hardened in their sinful practices.  Even the language[vi] becomes a stumbling block especially in cities and foreign lands when a plethora of people of various cultures live.  In some major cities, if you walk one block, suddenly, everybody is speaking a different language.

But by the grace of God, this teaching of the transgressors in any setting can be effective as He alone leads.  One need only recall the wonderful story of the late G. Gordon Liddy who was publicly humiliated by his role in the Nixon Watergate scandal in the 1970s and imprisoned.  But in prison he was led to the gospel and from that he was able to bring countless numbers of people to Christ through his ministry, which continues even today after his death.[vii]   The ‘transgressors’ are everywhere – not only in prison, but also the executive suites of the big corporations or government, our schools and workplaces or the living rooms of our homes.  So the preachers are needed there – everywhere. And as Jesus says, amazingly, ‘The fields are white for the harvest.’ (Jn. 3) and people are being made ready by God through their personal ‘moments’ with Him long before any preacher or teacher shows up.

The Wicked Shall Return

Before closing, I find something curious here that is incredibly hopeful as well.   David says, “The wicked shall return…”  He does not say, “The wicked shall come…” but in using return he is implying that the wicked (e.g. you and me) have already been with God before and this is a return. This hearkens, of course, the story of the Prodigal Son who returned home to the Father, but really it points to something important in the cosmic understanding of our human existence.  From the beginning, we were somehow ‘with’ God, but then left Him. It certainly is a reflection of the Christian world view – hearkening to the Garden of Eden story in Genesis 2.  It’s a place that somehow(?) we know inside that has really been prepared for us to return to.(Jn.14:2)  While it might seem new, there is a place inside of us that is reserved for God alone, and when we return, we have access again to God who is there, and has been there all along.  As some Fathers of the Church would say, our journey in sin is always a journey away from our very selves, and our return through repentance is when we become truly ourselves, and truly human.

The Lord has come to show us that even if we are wicked, through repentance and His forgiveness, we need not perish. Ω

[i] It can be a very helpful spiritual exercise to revisit moments in one’s life when God was breaking through.  Sometimes, because the circumstances of those events was so painful, it’s hard to go there.  But discovering the ongoing grace coming forth from those moments is akin to the Church’s continual revisiting of the Cross, where despite the anguish and pain, the grace of God’s love shown forth.  Every believer has her or his moments of grace that can be visited.  

[ii] The conversion of the centurion Cornelius is another prime example, in Acts 10.

[iii] By moments of sheer grace, I mean something akin to what St. Mary of Egypt experienced.  Her conversion came through the events of her life, but it was an experience of grace that drew her to the celebration of the Liturgy on the Feast of the Exaltation of the Holy Cross.  While her desire to enter the church was thwarted at first, her joyful experience of Holy Communion that that day would sustain her for her decades in the desert in the strictest ascetical suffering. Joyful moments where God’s presence is unmistakable often become the moments that crack our awareness and we see ourselves as utterly unworthy of Him and His mercy and love.

[iv] I believe I’ve mentioned above, but it bears repeating… I think this is perhaps the singularly greatest failure that takes place in the Church today.  We don’t often continue to make disciples through a process of spiritual formation and teaching, but assume the new converts have ‘arrived’.  It’s consistently true in Orthodox, Roman Catholic and Protestant churches.  My opinion.

[v] The Parable of the Talents is telling.  The man who fails in being the steward of the treasure is the one who greatly feared the Master so he buried the talent.  He never realizes how gracious the Master is in the first place in showing him love and trust, entrusting him such a great treasure and the opportunity to serve Him through it.  (Mt. 25:14-30)

[vi] The Church honors specially the missionary work of Ss Cyril and Methodius who evangelized the (then) heathen Slavs who were enemies of Constantinople. Although they were Greeks, they learned the Slavic language and eventually developed what became the Cyrillic alphabet to allow them a written form of language that would serve to provide a means for the scripture and teaching of the Church to be communicated to them.

[vii] I don’t hesitate to bring examples from non-Orthodox Christians as examples because they too can reflect the same grace in their lives inspired by the One Holy Spirit, unto the salvation of souls through repentance.  While their message may have weakness or flaws, they should not be inhibited or discouraged when the fruits are being born through their lives by grace. (Lk. 9:49f)

Author: Fr Robert Holet - UOC of USA Office of Stewardship

A semi-retired Priest of the Ukrainian Orthodox Church of the USA.

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