Another Letter to the Church: Blessed Man, Woe, Man!

What Jesus really said about prosperity.

"Christianity, if false, is of no importance, and... if true, of infinite importance. The only thing it cannot be is moderately important."

C.S. Lewis, Author & Oxford/Cambridge scholar/theologian.

I’ve been sitting on this second Blessed blog installment since early June, when my internal conflict and trip to Italy stalled progress. Since then, I got busy with paying work, a handy, avoidant escape. Yet God just would not let me call this in, preach a resentful rant, or duck it altogether, so I’ve been wrestling.

I find God honors honest wrestling—sometimes with answers; more often with the grace to accept mysteries or truth we don’t like.

Most of you know I do my messy spiritual processing in public, and you say my transparency helps you. I’m so glad, cuz here I go again. I reassure myself that Jesus and our Bible friends modeled messy vulnerability. That’s why recovery meetings seem more like authentic early church to me than church itself. The hypocrisy hurts less without a la carte Bible quotes.

Wrestling with Blessing

First I wrestled with my own persistent struggles, which forced me to reflect on Christ’s countercultural notion of blessing.

Next, I felt a little hypocritical preaching poverty while galavanting through the Tuscan tourist spots, though my prosperous and generous brother picked up most of the tab.

Micro-rant: Then I wrestle(d) with my resentment—indignation at rich Christians who watch others writhe in need with entitled indifference, layering insults with judgments to justify their greed, often legitimizing vain ambition with religious facades (Please read Matthew 23). There's no version of Christianity where this is OK, no matter how sweet your tone, how big a check 10 percent is for you, and how much scripture you quote.

I truly want to know how I can avoid that. They're not a different species, after all.

I've learned that it may not be my human heart that's bothered by this wrong; It may be the Holy Spirit in me who's grieved. Gulp.

I also had to admit I didn’t want to face Jesus’ version of blessed either. I much prefer the prospect of painless, prosperous, popular living. Bali and Botox, please.

I’ve been forced to wonder if those early Christians like Francis and Frediano (and Buddha, BTW), and many others since who abandoned great wealth and suffered had it right. Sigh.

My son and I loved every cappuccino, cobblestone, and church but couldn't help but ponder the price.

Italy complicated matters further. Poverty and saintly sacrifice sat cheek to cheek with opulence and excess, ironically most visible in the churches.

I admit I can run from righteous indignation at the oppressed poor to striding glamorously through Heathrow airport all in the same day. (Lord, have mercy on me, a sinner.)

Mind you, our Good Father doesn’t begrudge us good gifts. But when wealth shifts our focus away from Him, or bankrolls pride, selfishness, exploitation, or abuse of power, He is evidently angry. Very angry. For our sake...and the sake of those harmed by our self-indulgent neglect and abuse.

Finally, and maybe worst of all, I had to reckon with my people pleasing, and how this blog might land like a one-wheeled jet with an engine fire. Yet, God kept prompting.

Disclaimers: Before We Get All Defensive

Any talk of money is loaded, especially when you have too little or too much. That’s why Jesus spoke of it so often.

For some, this blog may feel comforting. For others, rattling. Either way, it can be game-changing. Recovery offers a spiritual axiom: when we’re disturbed, it usually says something about us. Scripture agrees (Matthew 7). Don't fleece or flee whatever comes up for you. Face it. Talk to God about it.

La Pietà di Michelangelo.

You may be feeling Holy Spirit conviction and godly sorrow, and you sure don't want to run from that. That's the good kind.

There’s no doubt scripture is difficult —especially in the New Testament, which challenges so many of our cherished ideals. Mind you, it’s the same God from beginning to end, but Jesus really threw a wrench in the works-- including his definition of blessed.

In the Old Testament, material prosperity and achievement were signs of God’s favor for Jews. In the New Testament, not. Jesus’ definition of “blessed” runs opposite to what most Christians celebrate. There is no New Testament prototype for the prosperous pastors or ministries so common today. Nada.

This idea that we can somehow earn, deserve, or are entitled to not only heaven, but “good stuff” of our own definition this side of heaven is insidious, intoxicating, and deadly. Equally toxic, is our notion of blessed.

 A sliver of the 94' altar of St. Peter's Basilica by Bernini.

Liberation, Not Condemnation

Even so, I know better now that God’s motive is always love, no matter what it feels like. Isaiah 61, which Christ reiterated at the launch of his ministry, is both my comfort and my compass:

“The Spirit of the Lord is on me,

    because he has anointed me

    to proclaim good news to the poor.

He has sent me to proclaim freedom for the prisoners

    and recovery of sight for the blind,

to set the oppressed free,

to proclaim the year of the Lord’s favor.”

Jesus, Luke 4:18-19 (NIV; See also Isaiah 61:1-2)

Right now, I’d like all of us to carry this verse in our pocket so we can filter the hard stuff through Christ’s loving intent, even when His words sting.

(I have to make an amends on this verse, which I'll share later.)

Not Us and Them…

I also want to issue a disclaimer that this is not rich-bashing or poor-pitying. Quite the opposite! It's yet more evidence of our shared humanity. As I've been saying for a while now, it's not us and them, it's us and them. We all risk the blinding seduction of money, power, and prestige, AKA E.G.O. That's unifying and equalizing truth our world sorely needs today with epidemic, narcissistic greed making a mess of things. Let’s remember that we're all in this together and that there is a solution we’ll explore later.

I’ve been on both ends of economic spectrum and can go from zero to world domination in 90 seconds. It can happen to anyone.

Galleria Vittorio Emmanuel II, Milano, a spectacular, historic shopping mall built in 1877.

I have repeatedly witnessed and experienced this cataracts of greed in extraordinary, well-meaning people who devolved into petty evils under the influence. Falling prey to the lures of fame and fortune, I personally traded the God-given dream of my meaningful cottage business, MightyTykes, for my investors’ more greedy, grand vision — and lost it all. I am wary and want to be wise.

Reality Check

Greed is non-denominational, too. Kenneth Copeland is worth $750 million.

The Vatican’s holdings are estimated at $300 billion, yet they operate with a $94 million annual budget deficit. Yesterday, the FBI raided a Tampa megachurch accused of financial misconduct (Kingdom of God Global Church). Leaders preached prosperity while exploiting members. I'll bet they didn't start that way.

These aren’t outliers. They are warnings of what happens when unchecked indulgence diverts our gaze from God. Greed not only intoxicates, it blinds. Many start out sincere, even sober in faith, but without moderation, open hands, and ongoing repentance, evil gets a grip. God lets us have our way, and blindness sets in. There but for the grace of God go we. How?

Guideposts

In early June, I was prompted to start this mini series on being “blessed,” something Jesus sees quite differently than most contemporary Christians, let alone the world at large.  Around the same time, I was invited to be a guest panelist on Guideposts Pathways to Happiness, a webinar on how to attain and retain happiness, even when life is challenging—personally or globally.

Coincidence? I think not. (I hope you’ll register!).

Is joy possible during trying times? God says it’s not only totally doable, it’s most especially doable under duress. I have experienced this paradox a lot, but at that particular moment, I wasn’t feeling it at all, which is why I went looking for answers.

My trip to Italy raised more questions that begged answers.

How like God to lead me to teach me! He likes us to share what we learn.

The Upside-Down Kingdom

My first blog was about In the Sermon on the Mount. Christ says we're blessed if we're broken, needy, grieving and grieved by sin and injustice, longing for righteousness and peace, pure-hearted and humble, all while being persecuted and slandered for it all.

Sheesh. Blessed? Christ, help me see!

The Sermon on the Plain, delivered at a different place and time, echoes the same blessings, but makes the material angle even sharper:

“Blessed are you who are poor, for yours is the kingdom of God. Blessed are you who are hungry now, for you shall be satisfied...But woe to you who are rich, for you have received your consolation. Woe to you who are well fed now,  for you will go hungry.” Luke 6:20–26

Gee whiz, Jesus! Not only poor in Spirit, but pocket poor?

Of course, both sermons promise heavenly rewards for Christ’s hard definition of blessing. But it’s not much comfort this side of heaven when bills pile up, DOGE cuts loom, food prices rise, or nations are plundered by Oligarchs, Kleptocrats, or Plutocrats (I had to look those up)--with or without armed militias.

And the woes! Whoa! It sounds like Jesus says being rich is a very bad thing. I mean, extremely bad. (Pause for liberation versus condemnation check.)

I feel a little ridiculous saying I don’t necessarily agree with Jesus. I mean, really? Despite my currently modest means, and decades of living on the creative edge of feast or famine, I would greatly enjoy a windfall or just steady income and the ease, comfort, and blessings money buys. But I definitely want to guard against the death spiral Jesus warns of.

This is good time to pause and indulge my inner nerd.

Defining Terms: Meanings Matter

In Aramaic and Greek, “blessed” means happy, divinely favored, spiritually full, healed, resisting corruption, possessing integrity. Good stuff!

Speaking of “rich,” the term used in the sermon refers to material wealth, possessions, and power.

Oxford defines greed, which shows up elsewhere in scripture, as “intense and selfish desire for something, especially wealth, power, or food.”  

Enlightening.

The fantastic Duomo of Milano, that fueled my inner tension.

Greed is sin. Sin, SIN, sin, SiN (aka defects). Let's please normalize the term again. Unless we agree with God about what sin is, we can’t be set free.

We sure don't feel “blessed” to be poor and persecuted in spirit or pocket, yet Jesus says plainly that we are. Richly blessed.

So what are we to believe about what’s woeful or wonderful? How can we bridge that giant gap between our senses, painful experience, and Christ's words?

Blessed or Distressed?

REPEAT: Jesus’ definition of “blessed” is the opposite of everything Christians seem to believe, in most any church or denomination, ancient or evangelical.

Are we to believe Jesus or our best thinking or self-serving definition of blessing?

Our misunderstanding explains a lot—if not all—of our problems as individuals and as a society, particularly right now when the greedy chickens are coming home to roost and lay some pretty rotten eggs.

The yardstick we use to measure the goodness, godliness, or value of people, places, or things--including pastors or churches--doesn't jive with Jesus.

Does it matter?

Depending on our beliefs, yes, there are major implications. Actually, there are major implications regardless of our beliefs because God is God and We. Are. Not.

What God Says About Wealth

I’m going to pass the buck and let The Word do most of the talking.  If we don’t like what he says, we can talk to Him about it.

Who's Your Master?

The Sistine Chapel, Vatican Museum

“No one can serve two masters. …You cannot serve God and money.” Matthew 6:24 (NLT)

“It is easier for a camel to go through the eye of a needle than for a rich person to enter the Kingdom of God!” Matthew 19:23–24 (NLT)

“They promise freedom, but they themselves are slaves… You are a slave to whatever controls you.” 2 Peter 2:19

Most of us know the temptation: joyless jobs pursued solely for money, family or health neglected for the bigger paycheck, measuring worth by assets, or buying love, loyalty, and identity only to find them hollow. We can find ourselves using money to control others or vice versa.

Deepened Discontent

“She out of her poverty has put in everything she had.” Mark 12:44 (NLT)

“I have learned how to be content with whatever I have… for I can do everything through Christ, who gives me strength.” Philippians 4:11–13 (NLT)

Don’t love money; be satisfied with what you have.” Hebrews 13:5  (NLT)

Ironically, the more we have, the more we want — yet satisfaction is fleeting. We can find ourselves coveting or hoarding, never slaking the deeper thirst. Believing our affluence should make us happy, secure, and attractive can leave us bewildered and despairing when it doesn't. It's not the money, really; it's the idol it so easily becomes.

Dastardly Deceptions

“The deceitfulness of riches… choke the word.” Mark 4:19 (NLT)

“…craving money, hey] have wandered from the true faith and pierced themselves with many sorrows.” 1 Tim 6:10 (NLT)

Command those who are rich in this present age not to be haughty, nor to trust in uncertain riches but in the living God, who gives us richly all things to enjoy. 1 Tim 6:17 (NLT)

Money can buy false comfort and transactional relationships that leave us empty and disconnected.  I've had people try to woo me with their money instead of their true selves, an obstacle to connection. Money muddies the waters of true love.

Unchecked wealth can lead us to feel entitled or superior, generalizing our prowess to mean we're wise or good with God. Finally, the power and influence money buys can blind us into self-deification, outright abuses, and gateways to other sins that destroy...The devil is laughing all the way to the bank.

Once a revered apologist, Ravi Zacharias began with sincerity but ended in horrific abuse fueled by unchecked power, sick sexual compromises, and secret funding streams. Blinded, not blessed.

Greed: The Church’s Most Minimized Sin

“Then he will say… ‘Depart from me, you who are cursed… For I was hungry and you gave me nothing to eat…’” Matthew 25:41–45

“If someone has enough money to live well and sees a brother or sister in need but shows no compassion—how can God’s love be in that person?” 1 John 3:17

 If a brother or sister is naked and destitute of daily food, and one of you says to them, “Depart in peace, be warmed and filled,” but you do not give them the things which are needed ...faith without works, is dead. James 2:15-17

We can’t rationalize a crystal cathedral or a private jet...or privileged prosperity.

Jesus preached on dusty hillsides with no place to rest His head.

We cannot ardently invoke the "Acts II" church without recognizing they lived communally, sharing resources, and suffering greatly to fulfill the Great Commission.

Judgment Begins with Us

“For the time has come for judgment, and it must begin with the house of God.” 1 Peter 4:17

“Woe to you...you hypocrites! You give a tenth of your spices—mint, dill and cumin. But you have neglected the more important matters of the law—justice, mercy and faithfulness...“Woe to you...you hypocrites! You clean the outside of the cup and dish, but inside they are full of greed and self-indulgence...“You snakes! You brood of vipers! How will you escape being condemned to hell? Matthew 23:23,25,

The lavish tomb of St. Peter — the disciple who asked to be crucified upside down. Would he recognize this as honoring him, or as missing the point?

“Where your treasure is, there your heart will be also.” Matthew 6:21

“Look here, you rich people: Weep and groan with anguish because of all the terrible troubles ahead of you.” James 5:1

Ananias and Sapphira (Acts 5) were struck dead for withholding money from the community and lying about it. The rich man in Luke 16 was condemned to hell for ignoring Lazarus begging at his gate.

That's pretty intense and there's more!

A spectacular view of the Palatine Hill — the “Beverly Hills” of ancient Rome — with its private walkway to the Colosseum, where Christians were once fed to lions for sport.

Separation & Sobriety in the Last Days

“Do not associate with anyone who claims to be a believer yet… is greedy. Don’t even eat with such people.” 1 Corinthians 5:11

“People will love only themselves and their money… They will act religious, but reject the power that could make them godly. Have nothing to do with them.” 2 Timothy 3:1–5

That's an order, soldier!

Self-Assessment Questions

After all this, where do we stand?

Security: Do I look to money (savings, income, possessions) to make me feel safe, instead of relying first on God’s care and promises? Have I used money to “buy” love, loyalty, and favor?

Trust: When I feel anxious, do I pray—or do I obsess about my finances, hoplan excessively, or seek control through money?

Identity: Do I measure my worth, success, or dignity by what I earn, own, or owe compared to others? Do I consider myself superior because of my assets or achievements?

Obedience: Am I willing to compromise my values (honesty, rest, generosity) in order to gain or protect money? Have I exploited or abused vulnerable people for personal gain or allowed others to exploit or abuse me for money alone?

Debt: Does my spending or indebtedness reveal a deeper slavery to money—whether through fear, pride, or escape? Do I see debt as a spiritual warning light, not just a financial one?

Generosity: Am I quick to share what I have, or do I hoard for fear that God won’t provide enough? Do I feel entitled and show indifference or contempt for those who struggle financially?

Surrender: If God asked me to give something up—income, a career path, a lifestyle—would I freely obey, or would I resist?

Covetousness – Am I inclined to envy, desiring more than I have or what others have?

And if my unhealthy attachment to money isn't a problem, what is (LOL)?

God’s Kingdom Economy

The Christian standard:

“Sell your possessions and give to those in need. This will store up treasure for you in heaven!” Luke 12:33

Jesus told him, “If you want to be perfect, go and sell all your possessions and give the money to the poor, and you will have treasure in heaven. Then come, follow me.” Matthew 19:21

“All the believers devoted themselves to the apostles’ teaching, and to fellowship, and to sharing in meals … They shared their money and possessions with those in need.” Acts 2:42–47

“All the believers were united in heart and mind. …There were no needy people among them, because those who owned land or houses would sell them and bring the money to the apostles to give to those in need.” Acts 4:32–35

There is a Solution

Jesus is so unambiguous and extreme on the subject of wealth! I admit I'm still wrestling about how to guard against the perils He warns of so forcefully and I've experienced so painfully.

We cannot deny what Jesus and the early Christians preached and modeled.

Can Christians even be financially rich, I ask myself?

I think the greatest guardrail against greed is to give a lot of it away, without fanfare or strings attached. To recognize everything we are and have is His and is to be shared for the common good for His kingdom and glory.

That's what He seems to say. That's what they did back in the day.

It’s just that simple...not easy. It requires supernatural Grace. Grace has a name.

Good News

Rich or poor, if your heart is heavy, don’t despair. Jesus only exposes to heal, help, and restore us when we re/turn.

Jesus longs to free us from anything that enslaves, harms, or hinders our relationship with Him. For now, we still enjoy the favor of His grace and the opportunity to seek His mercy, forgiveness, and healing.

Our Father's loving discipline is mercy that saves us from far worse consequences. That's a blessing. And that leads me to...

My Amends

In a few earlier writings, I’ve joyfully noted that when Jesus announced His ministry in Luke 4:18–19, He stopped short of the second part of Isaiah 61:2. He proclaimed “the year of the Lord’s favor” but omitted “the day of vengeance of our God.” That omission is intentional, because the day of vengeance will come when He returns to judge the living and the dead.

So, if LOVE doesn't compel us, maybe fear of God will.

PRAYER

Lord, reveal any way money, property, power, or prestige has taken Your place in my heart. Teach me to depend on You with faith and open hands. Break the chains of fear, pride, or greed, and lead me into the freedom of generosity and trust. Please have mercy on all of us. In Christ’s mighty name we ask it. Amen. Thank You. I love You.

Dig Deeper: OpenBible – Rich People