Esau: The Son Who Couldn’t Win, Part 1
In Genesis 25–28, we find the story of twin brothers, Jacob and Esau. Their “war” with one another grows because of parental favoritism and leads to lifelong consequences for many.
Explore with Pastor Chuck Swindoll three lingering lessons from Esau’s life. As you study his story, you’ll uncover truths about instant gratification, family dynamics, and more.
Reject favoritism in your family. Invest in your children and reap the benefits!
Bill Meyer: We're drawn to stories. Always have been, always will be. The Bible overflows with them, not as fairy tales, but as raw, honest accounts of real people facing real struggles.
Today on Insight for Living, in his biographical series called Fascinating Stories of Forgotten Lives, Chuck Swindoll invites us to meet Esau, a man whose life was marked by tragedy and deep disappointment. It's a shocking story that includes family dysfunction, parental favoritism, and irreversible choices. Yet woven through this ancient drama runs the golden thread of God's sovereign purpose.
Chuck Swindoll: Let's bow for prayer together. Will you join me? Our Father, we acknowledge that You are our God and Your Son is our Savior, and Your Word is our solitary reliable source of truth.
In a world of many voices, many messages, many convincing words, give us a simple appetite for the things that come from You and a satisfaction that in coming to You and hearing from You, we have found the best there is.
As we undertake this series, may we see within the truth of Your book, this ancient Old Testament, truths to live by, stories to remember, lives to give us warning and others to give us hope that we might find a pattern that unravels some of the mysteries of life.
Thank You in advance for the things to be learned and the conviction upon which to respond and to act and ultimately the changes that will occur because we have risked again exposing ourselves to the truth of Your written Word. In the name of Jesus Christ we pray, amen.
Bill Meyer: You're listening to Insight for Living. To dig deeper into these fascinating stories of forgotten lives, purchase the spiral-bound Bible study workbook for this series at insight.org/offer. And now the message from Chuck Swindoll about Esau, the son who couldn't win.
Chuck Swindoll: We never outgrow our love for a story, do we? There is something compelling, something magnetic, something altogether unique about a story. When Jesus was faced on this earth during His ministry with opportunities to communicate truth, He often chose a story.
And in some cases, He chose stories rather than any other method. Sometime to veil the truth, other times to explain it and illustrate it. But stories seemed to be one of His favorite kinds of communication style. Sometime the stories we hear are true, and the reality of them strikes us, impacts us.
We'll read a story in the newspaper or in a magazine, and journalists, by the way, are forever on a search for a story. A story that has intrigue and excitement and perhaps struggle and heartache, because they have learned over the years that there's something about a story that keeps people reading.
Clarence Macartney years ago at the First Presbyterian Church in Pittsburgh came to be known for his ability to tell great stories. I remember as a little boy, by the way, not having heard Dr. Macartney but having heard a number of preachers, I remember recalling years later a number of the stories that were told.
I couldn't remember the sermon, and I often couldn't remember even the scriptures, but I would not forget and to this day, I can still remember some of the stories. He was a master at storytelling. In one of his books, and I think I own all of Macartney's books, he writes this about stories:
"The mind of man delights in a stirring scene or spectacle. Whether it is a battlefield of temptation or an imaginary scene of triumph and glory in the heavenly places. Let the preacher remember this and throw open as wide as he can the golden gates of imagination. Napoleon said, 'Men of imagination rule the world.' The preacher of imagination is the prince of the pulpit." And he was indeed that.
There is an amazing thing about capturing a truth in story form. So let's say a little bit about stories since this is a series on great stories out of the Old Testament. Let me say some things, and I mean just a little bit, about stories themselves and what makes them interesting.
What is a story? Well, a story is a narrative. It is an account of incidents that usually revolves around people and usually includes a plot. The plot in the story is the plan. And it is that plan as it unfolds that holds our attention.
Great storytellers have the ability to hold the listener in suspense. Great story writers do not tell you all of it at the beginning but they leave you waiting, interested, wondering, sometimes saddened, sometimes excited about how the plot will unfold.
Now, what makes a story interesting? Well, stories form in our minds certain settings. They allow our imaginations to soar and we're able to leave the present humdrum and rather familiar world in which we live and we're able to move into the realm of the unknown.
We can see ourselves in the story that we're reading or we're hearing. We can draw lessons from those stories. The best kind of stories have within the plot these elements: surprise, struggle, romance, courage, loss, gain, and frequently the stories leave us with a sense of encouragement.
I don't know if you remember the lyrics of one of the old songs out of the Second World War made popular in the film Casablanca, but the lyrics of this song illustrate for me the genius of a story. "It's still the same old story, a fight for love and glory, a case of do or die. The world will always welcome lovers as time goes by."
There's something timeless about great stories. And I have found, tucked away in the folds of the Old Testament, the reason the truths are remembered is that they are placed before us, unlike the New Testament, they are placed before us in story form.
But before we look into the Old Testament section I want to look at in this study, turn first to Romans 15. And I'm looking at a single verse in the 15th chapter of Romans, it's the fourth verse. We've looked at it before, and so just the reading of it is all that's necessary.
Romans 15:4: "For whatever was written in earlier times was written for our instruction, that through perseverance and the encouragement of the scriptures we might have hope." You may not know this, but that verse has reference specifically to the Old Testament.
Whatever was written in earlier times. Paul wrote this verse before any of the New Testament had begun to be compiled. Certainly before it had begun to be distributed. So he's referring to the scrolls of the Old Testament written in earlier times.
He states that through the perseverance and the encouragement—I suppose he has in mind through the perseverance engaged in studying the scriptures and through the encouragement from those pursuits, we find ourselves full of hope. That's my main goal in this series, is to help build a reservoir of hope in your life from the stories that we uncover out of the Old Testament.
So without further delay, turn back to Genesis chapter 25. And we're going to pull a story from this first book of the Bible, a story that may be familiar to some of you, but before we are through in a little bit of time, you may discover that you really didn't know a lot about it or as much about it as you thought. I found that true in my own life.
Now, please understand as we begin this series that there is not one life we're going to study in the Old Testament that was supernatural. Some of the lives we will uncover have supernatural power. They're given that power by God.
Some of the people who evidence that power are even able to work miracles—not the one we're looking at in this study, but some of them we will look at in days to come. But all of these people we are looking at are folks just like us. In the words of James, Elijah was a man of like passions as we are.
If you will do this, it will help: remove all halos from above the heads of all the people in the Old Testament. Take away all of the aura, not all of the respect, but all of the aura that keeps you distant from these people. Otherwise, you will hold them at such a distance you will not see yourself in their lives.
These are stories of people just like you and me. They went through similar situations we go through. They lived in a different era. Times were perhaps more primitive, rugged, not nearly as comfortable, certainly not as modern.
But these are men and women of like passions. They are ordinary, garden-variety human individuals who knew nothing of their future and only at times knew something of their present. They must have wondered at times what life was all about.
Now that we've had years to look back on them, we can unravel many of the mysteries that they lived with during their lifetime. I want us to study in this particular story the life of a man named Esau. I'm calling him the son who couldn't win.
I have a feeling in all honesty that some of you hearing this story, some of you for the first time hearing this story, will have little difficulty identifying with some of the struggles Esau had. My Bible is open to Genesis 25, verse 19, which is one of the earlier references to the genealogy of Esau.
Let's say a word to begin with about his birth and childhood. "These are the records of the generations of Isaac, Abraham's son. Abraham became the father of Isaac. And Isaac was forty years old when he took Rebekah, the daughter of Bethuel."
Verse 21: "Isaac prayed to the Lord on behalf of his wife because she was barren, and the Lord answered him and Rebekah his wife conceived." Before I go any further, let me put to rest a misunderstanding.
The immediate thought after you read verses 20 and 21 of Genesis 25 is that shortly after Isaac prayed, God caused her to conceive. Wrong. You remember reading that he was 40 years old when they married? Look at verse 26, the last line. Isaac was 60 years old when she gave birth.
We get a little impatient in our prayer because we have to wait a week or two, a month or two. How about 20 years? And how about being 40 years old realizing that you don't have forever, wanting to have a family, asking God to bring that to pass and then it's not until 20 years later God says yes?
But we're getting ahead of ourselves. Let's go back to verse 22. "The children struggled together within Rebekah, and she said, 'If it is so, then why am I this way?'" So she went to inquire of the Lord. This was before there were sonograms.
This was before there were obstetricians, gynecologists, people with those high-tech pieces of equipment. She had no idea she had twins within her. All she knew was that there was trouble within her. There were wrestlings within her womb.
There are mysteries known only to a mother that are known to no one else. And she felt within her changes and conflicts and struggles going on within her. She had no idea that she had the beginnings of a war within her own body.
And so she inquired of the Lord, and in those days, the Lord spoke audibly to those who inquired of Him. And He said to her, "You don't simply have two children, you have the roots of two nations in your womb. Two peoples shall be separated from your body. One people shall be stronger than the other."
Now note this: "And the older shall serve the younger." She discovered from God's voice that not only was she to have a baby, she was to have two children. And that the conflict within her womb was by the design of God.
Never doubt that from the time of conception onward, you have life within your womb. Never let anyone try to convince you otherwise. And that God's design and purpose are both at work from the conception on in the life of your child or in your children.
She's told these will not be simply two children, they will be nations, and the younger will, as a matter of fact, be the most dominant. The older will serve the younger. When her days to be delivered were fulfilled, behold, there were twins in her womb.
And the first came forth red, all over like a hairy garment, and they named him Esau. So he's the older. And afterward, his brother came forth with his hand holding on to Esau's heel, so his name was called Jacob. And Isaac was 60 years old when she gave birth to them.
I don't want to look at the scene just theologically, I want to look at it humanly as well. Can you imagine being 60 years of age and the father of twins? Some people pray for twins. Usually they have not talked to people who have twins before they pray for twins.
It was always a great pleasure to me that we had our children one at a time. Some people do very well with twins and I'm always amazed. Yesterday morning, Cynthia and I decided we would take all five of our grandchildren to breakfast.
Both of our married kids when we called them and told them what we wanted to do on the evening before, both of them said, "Are you sure you know what you're saying?" We said, "We do, we are." So we picked them up, we put them in the car and we drove to the local pancake house.
And we began the process of unloading and going into the restaurant, all seven of us. And I will never forget the face of the gentleman sitting at the table next to us who had looked forward to a lovely quiet breakfast with his wife.
When we asked for three booster chairs and two high chairs, he really wasn't sure he had chosen the right restaurant. And we sat down and we had quite a breakfast together. I think Cynthia ate four bites of food in between serving the five kids. But that's five.
Just two. Isaac, however, was 60 years old when Rebekah gave birth to those boys. We're not told much about the childhood. We're told when the boys grew up, Esau was different from his younger brother Jacob.
Esau became a skillful hunter, a man of the field. Jacob was a peaceful man, living in tents. Nothing wrong with that. You will discover shortly after their birth, if you have had several children, how different they are one from another.
All five of our grandchildren are very different. One you place in the high chair and he's happy to sit there and if you leave him for an hour, all he needs is crackers to crunch up and stuff to drop on the floor and he's content.
The others are the prelude to a war just beginning to happen. So you have to keep them busy with other things. They are from the very same sets of parents, but they're very different. Esau was different from Jacob. Nothing wrong with that.
That's the way God designs them. But something is wrong in the next verse, and humanly speaking, it is the seed of great difficulty. Isaac loved Esau, but Rebekah loved Jacob. Isaac loved Esau because he had a taste for game.
I suppose Isaac was the outdoors type. He liked it that his boy liked to hunt. He liked the way his boy conducted himself and handled himself. He was a man. He was rugged. Rebekah liked it that Jacob stayed near the tent. Maybe he liked to cook.
He stayed around the house, we would say. He didn't like the field. Nothing wrong with the boys being different, but there is something wrong with this parental favoritism, which, by the way, haunts Esau's steps for the balance of his life.
When Jacob had cooked stew, Esau came in from the field and he was famished. And Esau said to Jacob, "Please, let me have a swallow of that red stuff there, for I am famished." Jacob said, "First sell me your birthright."
And Esau said, "Behold, I am about to die. So of what use then is the birthright to me?" And Jacob said, "First swear to me." So he swore to him and sold his birthright to Jacob. Jacob gave Esau bread and lentil stew, and he ate and drank and rose and went on his way.
And the chapter concludes with a brief commentary on the mentality of this older son: Esau despised his birthright. Doesn't mean much to English-speaking people. Really means very little to Americans. Birthrights are no longer significant, certainly not in Gentile homes.
James Hastings, one of the fine biographers of scripture, makes several statements about the value of a birthright and I want to refer to his writings so you will see what Esau forfeited. Just listen. To the birthright belonged preeminence over the other branches of the family.
Second, to the birthright appertained a double portion of the paternal inheritance. Third, to the birthright was attached the land of Canaan with all its sacred distinctions. Fourth, to the birthright was given the promise of being the ancestor of the Messiah.
The firstborn among many brethren, the Savior in whom all families of the earth were to be blessed. And fifth, to the birthright was added the honor of receiving first from the mouth of the father a peculiar benediction which proceeding from the spirit of prophecy was never pronounced in vain.
Such were the prospects of Esau. But in a moment of hunger, in a hurried moment of hunger where he says, "I'm famished," he trades his birthright and all of those blessings for a bowl of soup. It is the problem of instant gratification.
And when we come to the end of this message, I'll say more about that. But he bases an enormous amount of this decision on that instant moment of finding himself satisfied with a bowl of soup. He releases all of those blessings to his brother.
Bill Meyer: Many of us are familiar with the struggle between Isaac and Esau, but very few of us have heard their epic story told in quite this way. You're listening to the Bible teaching of Chuck Swindoll, and this is Insight for Living.
Chuck titled today's message Esau: The Son Who Couldn't Win. In this series, Chuck describes the Bible's often overlooked heroes. Their complex stories of both triumph and failure made an enormous impact and they show us that God uses every type of person.
Some, like Esau, had to learn the hard way. His pursuit of significance and affection often backfired, and we can learn from Esau's mistakes. To fully engage with this series of biographical sketches, Insight for Living has a resource that will let you linger over each Bible character at your own pace.
It's a spiral-bound workbook and it leaves room for making notes and observations. Look for our Searching the Scriptures Bible study workbook titled Fascinating Stories of Forgotten Lives at insight.org/offer.
If you'd like to listen to Chuck's messages, all 14 of them in the series can be accessed through the Insight mobile app. Download it from your favorite app store and start enjoying Chuck's teaching whenever and wherever you'd like.
If you've been wondering how to make a lasting difference through this Bible teaching ministry, here's one of the best ways: join Chuck Swindoll as a Monthly Companion. It's simple. You choose an amount that works for you and it comes through automatically each month.
If you sign up today, we'll say thanks by sending you Chuck's compassionate book called Clinging to Hope. This book is for anyone who's struggling with the question, why does God allow suffering in our world?
And if you're facing your own season of difficulty right now, you'll find the encouragement you need to keep going. To become a Monthly Companion, call 800-772-8888 or visit insight.org/monthlycompanion. I'm Bill Meyer, inviting you to join us when Chuck Swindoll describes Esau, the son who couldn't win, Tuesday on Insight for Living.
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If you want to explore Contagious Christianity: A Study of 1 Thessalonians with Pastor Chuck Swindoll, you can now purchase all 12 messages, all 12 corresponding Searching the Scriptures Bible studies, and the Insights on 1 & 2 Thessalonians Commentary as a set.
CD series of 12 messages, spiral-bound workbook with 12 Bible studies, and commentary.
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About Pastor Chuck Swindoll
Charles R. Swindoll has devoted his life to the accurate, practical teaching and application of God's Word. Since 1998, he has served as the founder and senior pastor-teacher of Stonebriar Community Church in Frisco, Texas, but Chuck's listening audience extends far beyond a local church body. As a leading program in Christian broadcasting since 1979, Insight for Living airs in major Christian radio markets around the world, reaching people groups in languages they can understand. Chuck's extensive writing ministry has also served the body of Christ worldwide and his leadership as president and now chancellor of Dallas Theological Seminary has helped prepare and equip a new generation for ministry. Chuck and Cynthia, his partner in life and ministry, have four grown children, ten grandchildren, and six great-grandchildren.
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