A Battle You Cannot Afford to Win – The Remarkable Story of Jacob’s Conversion

4x5 originalOne of the stranger affections of God in the Old Testament is the special love that God had for Jacob. His name, according to some means “grabber” or “usurper”. Even in the womb he strove and wrestled with his twin brother Esau. And though Esau made it out first, Jacob came forth grabbing his brother’s heel. Thus they named him Jacob (“grabber”).

And though he was a “mama’s boy” he was also a schemer, a trickster and an outright liar. His mother, Rebekah, favored him and schemed with him to steal the birthright from his brother Esau, by lying to his blind father Isaac and obtaining the blessing under false pretense.

His brother sought to kill him for this and he fled north to live with Laban, an uncle who was even a greater trickster and schemer than he. For fourteen years he labored for him hoping to win his beloved Rachel. In wonderful payback, Laban tricked him into marrying her “less attractive” sister Leah by hiding her appearance at the wedding. Jacob had thought he was marrying Rachel, but when the veil was pulled back: surprise! Only seven years later would Jacob finally secure Rachel from Laban.

Frankly, Jacob deserved it all. He was a schemer who was out-schemed. He was a trickster, a shyster, and an out-right liar who succumbed to all his own devices by someone more devious than even he.

Yet, God seemed to have a heart for Jacob. At the end of the day, God loves sinners like you and me as well. And in Jacob, a hard case to say the least, God demonstrates that his love is not based on some human merit. God knows and loves us long before we are born (cf Jer 1:5) and his love is not the result of our merit, but the cause of it.

There came a critical moment in Jacob’s life where God’s love reached down and worked a transformation.

It was a dark and sleepless night in the desert. And for reasons too lengthy to describe here, Jacob had come to a point in his life where he realized that he had to try and reconcile with his brother Esau. He realized that this carried risk, and that his brother might kill him, having found him (he did not, they were later to be beautifully reconciled).

Perhaps this was the reason for his troubled sleep, and perhaps too, his desire to reconcile with his brother pleased God. But whatever the reason, God reached down to touch Jacob.

We pick up the story at Genesis 32:21

I. DISTRESSED man – The text says, So the [peace] offering [to Esau]  passed on before him; and he himself lodged that night in the camp. The same night he arose and took his two wives, his two maids, and his eleven children, and crossed the ford of the Jabbok. He took them and sent them across the stream, and likewise everything that he had. And Jacob was left alone; and a man wrestled with him until the breaking of the day. (Gen 32:21-24)

Jacob is distressed. He has, somewhat willingly, and yet also for reasons of his own sued for peace with his brother Esau so as to be able to return to his homeland. How his brother will react is unknown to him. And thus he is distressed and sleepless.

And so it is for many of us that our sins have a way of catching up with us. If we indulge them, sooner or later we are no longer able to sleep the sleep of the just, and all the promises of sin now become bills that are overdue.

Having come to this distressed and critical place in his life, God goes to work on Jacob to purify him and test him. On a dark and lonely night in the desert, Jacob finds himself alone and afraid, and God will meet him. Note three things about how God works:

1. God brings Jacob to a place of isolation – This is difficult for God to do! Oh how we love distraction, noise and company. We surround ourselves with so many diversions, usually in an attempt to avoid considering who we are, what we are doing, where we are going, and who is God. So God brings Jacob to a kind of isolation, on a dark and sleepless night in the desert. The text says, And Jacob
was left alone; It’s time to think, it’s time to pray and look to deeper issues.

2. God brings Jacob to a place of confrontation – verse 24b says, and a man wrestled with him until the breaking of the day.

Who is this “man?” The Book of Hosea answers and supplies other details of the event: He strove with the angel and prevailed, he wept and sought his favor. He met God at Bethel, and there God spoke with him– the LORD the God of hosts, the LORD is his name: (Hos 12:4-5)

Yes, it is the Lord who wrestles, who strives with Jacob. God mixes it up with him, and shakes him up. And here is an image for the spiritual life. Too many today think God only exists to affirm and console us. He can, and does do this, but God has a way of afflicting the comfortable as well as comforting the afflicted. Yes, God needs to wrestle us to the ground at times, to throw us off balance to get us to think, and try new things, and to discover strengths we did not know we had.

3. God brings Jacob to a place of desperation the text says, When the man saw that he did not prevail against Jacob, he touched the hollow of his thigh; and Jacob’s thigh was put out of joint as he wrestled with him (Gen 32:25).

It is interesting to consider that God cannot “prevail” over Jacob. But though omnipotent, God will not simply overrule our will. And thus, in striving with Jacob, God can only bring him so far. But God will leave him with a lingering memory of this night, and the lesson that Jacob must learn to lean and trust.

He is a hard case so God disables him. Having knocked out Jacob’s sciatic muscle, God leaves him with the necessity to literally limp and lean on a cane the rest of his life. Jacob must learn to lean, and he will never forget this lesson, since he must physically lean from now on.

Thus Jacob, a distressed man on a dark desert night wrestles with God beneath the stars and learns that the answer to his distress is to strive with God, to walk with God, to wrestle with the issues in his life, with God. Jacob up to now has not well trusted and walked with God. He has schemed, manipulated and maneuvered his way through life. Now he has learned to lean, to trust, and realize he is a dependent man.

II. DEPENDENT man – The text next records: Then the man said, “Let me go, for the day is breaking.” But Jacob said, “I will not let you go, unless you bless me.”

If the “the man” is God, as the text of Hosea teaches, then it seems odd that God would have to ask someone to “let him go,” and for a mere man, as Jacob is, to say to God “I will not let you go” as if man could “not let” God do anything!

But the request of “the man” may also be understood as a rhetorical device, pulling from Jacob the required request. So the Man says, “Let me go!” But God wants Jacob, and us, to come to the place where we say, “I will not let you go!”

In saying, “I will not let you go,” Jacob is finally saying, “Don’t go, I need your blessing! Lord you’re my only hope. I need you, without you I am sunk”

God needs to get all of us to this place!

This critical moment has brought Jacob an insight that he must have God’s blessing, that he wholly depends on God. And this leads us to the next stage:

III. DIFFERENT Man – The text records: And the man said to him, “What is your name?” And he said, “Jacob.” Then he said, “Your name shall no more be called Jacob, but Israel, for you have striven with God and with men, and have prevailed.” (Gen 32:27-28)

Here is the critical moment. Jacob finally owns his name. Before he had lied to his Father Isaac who, when blind, asked him: “What is your name?” And Jacob lied saying: “I am Esau.”

But but after this encounter with God, Jacob finally speaks the truth saying, “My name is Jacob.” And in saying there is a kind of confession: “My name is Jacob…my name is deceiver, grabber, usurper, con artist, and shyster!”

Thus Jacob makes a confession, acknowledging all that his name “literally” implies of him has been true.

But receiving this confession, God wipes this slate clean and gives him a new name: Israel, a name that means, “He who wrestles, or strives with God.”

And in being renamed he becomes a new man. He is different now, he is dependent. He will walk a new path and walk in a new way, with a humble limp, leaning on the Lord, and striving with him, not against him.

And thus Jacob (Israel) wins by losing! God had to break him to bless him, and cripple him to crown him. Jacob would never be the same again, he would limp for life and always remember how God blessed him in his brokenness. Scripture says, A broken and a contrite heart, O God, thou wilt not despise. (Ps 51:17)

Postscript – There is a kind of picture of the “New Man” Jacob had become in the Book of Hebrews: By faith Jacob, when he was a dying, blessed both the sons of Joseph; and worshiped, leaning upon the top of his staff. (Heb 11:21) Yes, he had learned to lean. He limped the rest of his life. He needed a staff to support him. He learned to lean.

Have you learned to lean?

There is a battle you can’t afford to win, the battle with God. Yes, that is a battle you cannot afford to win! Learn to lean, and delight to depend: the story of Jacob’s conversion. How about yours?

21 Replies to “A Battle You Cannot Afford to Win – The Remarkable Story of Jacob’s Conversion”

  1. I’ve always wondered what this part of Genesis was saying. Thank you Monsignor!

  2. Hi Monsignor Charles

    Excellent article. However, one point – I have read so many times about Jacob having to wait another seven years before he got Rachel for his wife, but if you read Genesis 29 carefully you will see that Laban made him complete a marriage week with Leah, then he gave him Rachel as wife. Jacob had to work the seven extra years after he was given Rachel.


    1. Fair enough in terms of clarification, but the point is he had to work another seven years for her, he had to wait, that is, be detained another seven years for her.

      Laban replied, “It is not our custom here to give the younger daughter in marriage before the older one. Finish this daughter’s bridal week; then we will give you the younger one also, in return for another seven years of work.” (29:26-27)

  3. This article has wonderfully expanded my understanding of the passage involved. Now I see how Jacob had trained for his struggle in what is sometimes called, in the martial arts, “solo training” and how this had fostered his trickery and the short cuts involved in such trickery.
    Now I see how solo training has value but, without sparring, there is no interaction or a learning of how to interact. Jacob had solo trained and had tricked those of his family who were not used to using such means as trickery. Yet, when he dealt with Laban who had honed his skills, he was not ready for a worthy opponent. He had a lesson in humiliy about going it alone too much and, of how his ego had grown out of proportion when he made himself a “legend in his own mind” as I have sometimes done in my life.
    One time, recently, I ended up in a dispute over this passage and the other person insisted that this fight did not happen. However, I had gradually come to see this as anologous to a father/son wrestling match such as may happen in many families so I was ready; after my previous inner struggle and discussion with other people who I was fortunate enough to listen to. So, I managed to reply that a wrestling match was not always a fight – as in a battle for conquest by one over the other. Yet, Jacob did submit, in a way, but not as a servile person with the hopelessly and permanently broken spirit of a slave but as a respectful servant.
    The discussion ended before I could use my anology of a father/son sparring match. Sparring is for training both parties but especially the novice. The novice learns about interaction and limitations that must be addressed. The worthy father, who may have a black belt or more, does not degrade the white belted son or make him grovel. He just shows the limitations and encourages progress through a proper process as he allows the son to benefit from lessons well learned while showing the flaws in short cut lessons that involve such things as trickery.
    Your input leads me to re-assess and expand my thoughts here and the comments of others may be of great assistance. Especially if stated with facts, figures, logic and reason. I sometimes encounter, what seems to me, to be verbal violence and must admit that I am not receptive to any value there and have a struggle to avoid a judgement that shuts my mind from the value. Everyone has something of value to add and, I suppose that I have a lot to learn about that.

  4. Thank you for this wonderful reflection, about wrestling with God. This is something I will need to return to again and again.

  5. Wonderful piece, Monsignor.

    The lesson I always gather from Jacob’s life is that even after we “surrender” to God, we are not guaranteed a peaceful existance. So often, I wonder why my life is so difficult even though I am a child of God.

    Even after his conversion, Jacob led a sad life… all was not “happily ever after” (not that you imply this). His daughter Dinah was raped, and two of his sons slaughtered the men in another family to avenge her. Later, he believed for the rest of his days that his favorite son, Joseph, was dead – when in reality his own sons had sold the young man into slavery. Jacob’s brokeness lasted for the rest of his life. In his own words (to Pharoah) Jacob sums up his life by saying, “My years have been few and difficult.”

    Yet, he who endures to the end will be saved! Jesus assured his discipes that “many will come from the east and the west, and will take their places at the feast with Abraham, Isaac and JACOB in the kingdom of heaven”! (Matthew 8:11)

  6. Thank you for a very insightful article. You have helped me to understand the beauty behind this story and how it can apply to our own lives!

  7. Wonderfully clarifying. I can really use this passage for a prison bible study session.

    Peter—really appreciated too your father son “sparring” analogy.

  8. Msgr. Charles Pope,

    What a beautiful reflection on this passage.

    Your insight has enriched my understanding of this passage, thank you for that!

    In Jesus, Mary, & Joseph,


  9. The bible says that Jacob wrestled with God and prevailed, but you say that Jacob wrestled with God and lost. I don’t really understand that. I thought the part about Jacob finally saying his real name, the way you connect it back to his lying to Isaac, confession really, and thus earning him a new name, Israel, was neat and insightful. I also thought this part neat and insightful: “But God wants Jacob, and us, to come to the place where we say, “I will not let you go!””

    1. Well the text a little more complicated regarding the “prevail” part: When the man saw that he did not prevail against Jacob, he touched the hollow of his thigh; and Jacob’s thigh was put out of joint Which I interpret to mean that God put an end to the struggle forthwith when Jacob proved strong (stubborn?). i.e. Jacob ultimately did not prevail, but left the struggled “defeated” and limping but also different and leaning.

  10. Saint Augustine disagrees with your view.
    “And though he was a “mama’s boy” he was also a schemer, a trickster and an outright liar.”
    Augustine Contra Faustum, Book XXII;59. “This must suffice as a reply to the false accusations brought by Faustus against the three fathers, Abraham, Isaac, and Jacob, from whom the God whom the Catholic Church worship was pleased to take His name. This is not the place to discourse on the merits and piety of these three men, or on the dignity of their prophetic character, which is beyond the comprehension of carnal minds.”

    Also To Consentius, Against Lying; “24. Touching Jacob, however, that which he did at his mother’s bidding, so as to seem to deceive his father, if with diligence and in faith it be attended to, is no lie, but a mystery. The which if we shall call lies, all parables also, and figures designed for the signifying of any things soever, which are not to be taken according to their proper meaning, but in them is one thing to be understood from another, shall be said to be lies: which be far from us altogether…But if it be no lie, when things which signify one thing by another are referred to the understanding of a truth, assuredly not only that which Jacob did or said to his father that he might be blessed, but that too which Joseph spoke as if in mockery of his brothers, and David’s feigning of madness, must be judged to be no lies, but prophetical speeches and actions, to be referred to the understanding of those things which are true; which are covered as it were with a garb of figure on purpose to exercise the sense of the pious inquirer, and that they may not become cheap by lying bare and on the surface…They are accounted lies only because people do not understand that the true things which are signified are the things said, but believe that false things are the things said. To make this plainer by examples, attend to this very thing that Jacob did. With skins of the kids, no doubt, he did cover his limbs; if we seek the immediate cause, we shall account him to have lied; for he did this, that he might be thought to be the man he was not: but if this deed be referred to that for the signifying of which it was really done, by skins of the kids are signified sins; by him who covered himself therewith, He who bare not His own, but others’ sins. The truthful signification, therefore, can in no way be rightly called a lie. And as in deed, so also in word. Namely, when his father said to him, Who are you my son? he answered, I am Esau, your first-born. This, if it be referred to those two twins, will seem a lie; but if to that for the signifying of which those deeds and words are written, He is here to be understood, in His body, which is His Church, Who, speaking of this thing, says, When you shall see Abraham, and Isaac, and Jacob, and all the prophets in the kingdom of God, and yourselves cast out. And they shall come from the east and from the west and from the north and from the south, and shall sit down in the kingdom of God; and, behold, there are last which shall be first, and there are first which shall be last. For so in a certain sort the younger brother did bear off the primacy of the elder brother, and transfer it to himself. Since then things so true, and so truthfully, be signified, what is there here that ought to be accounted to have been done or said lyingly? For when the things which are signified are not in truth things which are not, but which are, whether past or present or future, without doubt it is a true signification, and no lie. But it takes too long in the matter of this prophetical signification by stripping off the shell to search out all, wherein truth has the palm, because as by being signified they were fore-announced, so by ensuing have they become clear.”

    1. An interesting quote, but an odd one too. St. Augustine seems to use a lot of allegorical techniques to reach his conclusion that somehow Jacob didn’t do what he seems plainly to have done or that somehow up in the ether of heavenly mysteries his lies and tricks are really incomprehensible to us. Frankly I have trouble following his argument and the translation you provide is very wooden, I have trouble following it simply in terms of sentence structure. But it is not my general approach to Scripture to presume that God gave us a text that is utterly incomprehensible. Why would God do that? Sure there are mysteries, but the sacred text is not completely opaque either. Neither do I find it necessary to call lies “prophetic acts” beyond our understanding. God’s first purpose is not to talk in riddles.

      As a preacher and teacher it is more my own approach to stick more closely to the sacred text’s straight-forward meaning, while I do not deny allegory and surely will not gainsay doctrinal understandings given by the Church. But in this matter St. Augustine is not the magisterium and the subject before us is not per se doctrinal. But as a straight-forward description of events and the personalities of our Biblical heroes the sacred text never shies away from speaking plainly of their sins and struggles. I find this approach very refreshing. These were men and women who struggled, sin and fell short. But they stayed in the conversation with God and God with them, and eventually they came to greater strength. But we are privileged to see them at their best, but also their worst. At least that’s my take on it. The plain meaning the Genesis text describes Jacob as I set him forth. He does plainly lie, play tricks and acts so badly that he has to flee for his life. Facts are stubborn things and all that I have taken is right from the text. He’s clearly no righteous dude and does need conversion which the text also shows.

      1. We covered this part of the OT in our BIble Study (Great Adventure by Jeff Cavins). You article, Msgr Pope, really enriches and complements our lessons about Jacob the ‘schemer’! I am keeping/sharing your article with my classmates!

        Thank you for your wonderful points for reflection!

  11. The book “Living a life that matters”, by rabbi Harold S. Kushner, has a very interesting intepretation on Jacob’s life. Though being a Jew, Kushner’s books, for those who haven’t read them, are the universal and sensitive kind. He’s the author of the popular “When bad things happens to good people”, a book that begun to became famous… thanks to very special Catholic readers; a congregation of nuns in Chicago.

  12. I have always wondered what the nature and significance of these parental blessings given throughout the old testament curtails and why only one of the offsprings could receive it. Can you explain in more detail?

  13. All the praises to my Lord!

    Wonderful interpretation of the story, Monsignor. All these years I used think how can God bless Jacob, such a cheater. But today after reading this I have understood perfectly that it was the U turn Jacob took, the new path he choose, with a humble limp, leaning on the Lord, and striving with him, not against him made him grab all the blessings from GOD.

    There are some parts in the Holy Bible which is difficult for me to understand. Could you help me how to find beautiful reflections like this to throw light into my mind while I am confused. Thanks for my friend Blossom for forwarding this. May God bless her and her family for enlightening me.

  14. I never thought you’d use the word ‘Shyster’ Monsignor. It gave me a good hearty laugh. 🙂

  15. +JMJ

    Thank you for a very insightful lesson on Jacob, aka Israel. I have always been taken by the fact that Jacob asks the angel (the LORD) who he wrestled with, “What is your name?” but gets no answer in return. The answer comes in time as Jacob learns to “lean on the Everlasting Arms”.

    Personally, I am living this ‘Jacob’ experience in my own life. In January 2008 I accepted an invitation from Bishop Hilary Okeke of the Diocese of Nnewi, to come to his diocese in Southeast Nigeria. As a Sacred Artist, I was to assist the new Diocese in adorning their Cathedral. This opportunity was an amazing gift from God, and I knew just what I was going to do and how to accomplish it. My first day in Africa was an unbelievable culture shock… but so full of myself, I turned the shock into bringing my cultural remedies to bear. In fact, Bishop Okeke, a very prudent and wise man, held his tongue until on the um-teenth time of having to listen to my advise, said,” My dear, you have the solution to every problem, don’t you?” That was my wake up call… but not the final blow to my pride. I was certain that I would be staying in Nnewi until my work there was accomplished… and since my previously unrealistic plans came to naught, then I might be in Nnewi forever. May of 2009 came and the Bishop and the Diocesan Council decided that the present Cathedral building was poorly built and was too small to accommodate the growing Diocese (it sat 4,500 people, but at two previous celebrations there were 8,000 and 10,000 people at Mass). Thus they began to tear it down; and I was given a new assignment, to be the Diocesan librarian. Over the next five months I cataloged and filled the stacks of the new library with hundreds of donated books. Then one fateful night during rainy season (when a slick green moss grows all over the concrete walkways) I fell in the dark and injured myself. After two months of pain and restricted mobility, I flew back to the States to take advantage of the wonders of medical diagnostic technology we take for granted, and Africa only dreams of. Tests revealed that I had torn my iliopsoas muscle, a bundled muscle, that is the major hip flexor. The treatment at my now chronic stage: rest and no intervention. The process of healing can take years! A consequence can be a limp when walking. I was 59 years old when the fall happened, and now, almost four years later, I still have pain and walk with a limp. Sadly, for many reasons, I have not been able to return to Nigeria. I pray that someday I will. BUT in the meantime, the LORD has really been at work in me. Many times I have struggled to stand and then walk away limping… thinking of Jacob. To admit that I have in my past behaved much like Jacob, wanting my own way and not leaning on the LORD, has been a crucial turning point in my life. Now I wait, as in a holding pattern, praying the Prayer Office every day and night, striving to attend Daily Mass, taking online classes in Biblical Theology and just waiting for the LORD to lead me on… to where and what, I don’t know. For now, “I’m just leaning…”

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