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Content Warning: This section of the guide includes discussion of death.
In Christianity, grace is defined as God’s unmerited, initiating, and costly favor that freely pardons and restores sinners. This concept stands as the book’s central message, presenting an alternative to both religious moralism and irreligious self-fulfillment: As the author states, “God’s reckless grace is our greatest hope, a life-changing experience, and the subject of this book” (18). This unconditional acceptance is free to the recipient but costly to God, as evidenced by the parable. The father runs to embrace the younger son before he has a chance to confess, demonstrating that God’s favor is initiating and unconditional, but it cuts into the remaining wealth of both the father and his elder son. The cost is significantly steeper when the parable is read allegorically as pointing toward Jesus’s sacrificial death to redeem fallen humanity. Keller’s conception of grace is therefore not a “cheap grace” that gives license to sin; rather, its immense cost motivates a transformed life. Its power lies in its ability to change the heart’s motivation from fear-based duty to a grateful and loving obedience.
A parable is a simple story used to illustrate a spiritual truth, usually by means of allegory. In the Bible, Jesus frequently employs parables to challenge his listeners’ core assumptions, and Keller argues that the Parable of the Prodigal Son is largely intended to rebuke the Pharisees’ grumbling about his welcome to sinners. The parable’s function is therefore not simply to comfort (by reassuring listeners of the father’s mercy) but to deconstruct and even offend. As the text states, “Jesus’s purpose is not to warm our hearts but to shatter our categories” (13). This power is amplified by the story’s open ending, which invites the audience of “elder brothers” to confront their condition and choose a response.
The Pharisees were one of two major branches of Judaism at Jesus’s time, the other being the Sadducees. The latter were the traditional priestly class, whereas the Pharisees emerged as a reformist sect that argued (among other things) for the importance of oral tradition alongside the written Torah. This makes the New Testament’s depiction of them as “religious insiders” somewhat ironic and ahistorical; the discrepancy may reflect the fact that their influence was more apparent in the non-elite spaces in which Jesus circulated, or it may stem from the fact that they became the dominant sect a few decades after Jesus’s death, when the New Testament was being compiled.
Regardless, Pharisees as portrayed in the Bible typically seek righteousness through strict obedience, thus serving as the archetype for the “elder brother.” Their complaint that Jesus “welcomes sinners” provides the immediate context for the parable, establishing them as its primary audience. Keller uses this historical group to represent the modern mindset of religious moralism, which he argues is a profound form of spiritual lostness. The book contends “Jesus is pleading not so much with immoral outsiders as with moral insiders” (12), explaining why those confident in their morality were offended by radical grace.
The idea of a “prodigal” God is the book’s central concept; the word portrays God as “spendthrift” with his grace. Keller notes that the term “prodigal” implies lavish and extravagant expenditure. This provides the thesis of the book, recasting divine love as initiating, unmerited, and costly. This lavish grace is displayed in the parable when the father runs to his younger son and restores him with the best robe, a ring, and a fattened calf without demanding repentance or restitution first. This radical welcome shatters conventional religious categories, deeply offending the moralistic elder brother. Keller emphasizes that this grace, while completely free to the recipient, is infinitely costly to the giver, a cost that is ultimately paid by Jesus Christ; the idea is thus central to the theme of Costly Grace and the True Elder Brother.
Keller uses the term “self-salvation project” to denote what he describes as the universal human drive to try to secure personal worth and control over life by either rejecting God outright or seeking to manipulate him through outward compliance (thus rejecting God’s providence in spirit). This concept is central to the claim that Both Brothers Are Lost, as it unifies the siblings’ seemingly opposite strategies, revealing that their core motivation is the same: to get the father’s things without submitting to the father himself. Keller also uses the character Salieri from the play Amadeus to illustrate this dynamic, showing how a life of strict moral observance can be a transactional bargain designed to put God in one’s debt. Recognizing this underlying Sin as Self-Salvation is crucial, as it means true repentance must go deeper than confessing behavioral failures. It requires repenting of righteousness that positions a person as their own savior, a project that stands in direct opposition to the gospel’s call to trust in God’s unmerited grace.
As Keller explains, sin in Christian tradition entails more than breaking divine rules. Rather, it is a basic attitude toward God that has structured human nature since the Fall—an inherent disposition known as “original sin.” Specifically, it’s an attitude of pride, which is often understood to be the sin from which all other sins flow. In Genesis, Adam and Eve seek to become like God by eating from the Tree of Knowledge, and this tendency to rebel against God’s authority, rooted in the belief that one can be one’s own savior and lord, persists in modern humanity. This condition of sinfulness is also what rendered Jesus’s death necessary in Christian teaching, as he atoned for humanity’s fallen state.
In keeping with this idea, the book argues that “sin is not just breaking the rules, it is putting yourself in the place of God” (50). This definition unifies the spiritual conditions of the younger and elder brothers, showing that overt rebellion and moralism are simply two different strategies for achieving the same self-centered ends. The elder brother’s moral record, for example, is the very thing that keeps him from entering the feast, illustrating how virtue can become a tool for prideful self-salvation. This deeper understanding of sin requires a correspondingly deeper repentance that addresses the root desire to live without God, and Keller argues that an appreciation of Jesus’s sacrifice is key to this shift.



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