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Keller suggests that the two brothers illustrate two basic paradigms people use to find fulfillment: moral conformity and self-discovery. The elder brother represents moral conformity. This approach prioritizes obedience to community standards (often religious) over one’s personal desires. The younger brother represents self-discovery, prioritizing individual freedom and self-actualization over custom and authority. Keller cites the film Witness as illustrating the basic tension. When an Amish widow, Rachel, falls in love with an outsider, her father-in-law warns that she is shaming him, prompting her to retort that his behavior is what is shameful.
Keller notes that contemporary Western society is split along similar lines, though individuals may combine these paradigms or switch between them over time. For instance, some religious people lead double lives in which they flout religious convention, while irreligious people can be intolerantly self-righteous. Keller argues that Jesus’s parable poses a “radical alternative” to these two paradigms, which are ultimately both self-defeating.
Keller explains the kind of sin that each brother embodies. The younger sins through “self-indulgent” living, which alienates him from his father (i.e., God). Keller suggests that this is what most people picture when they think about “sin.” By contrast, the elder brother is apparently respectful of God’s law. However, his rant about his father’s behavior reveals that he, too, is alienated from the father. Moreover, it is the “bad” son who ultimately accepts the father’s love, entering the feast while the “good” son refuses. His stated reason is his perfect obedience, revealing that his righteousness itself is his sin.
Keller observes that the brothers’ underlying motives are fundamentally alike. Both want the father’s goods but resent the father and his authority. The younger son uses defiance to get his inheritance, while the elder uses obedience as leverage, but both are in a state of rebellion against God, which can entail both “breaking [God’s] rules [and…] keeping all of them diligently” (42).
According to Keller, the parable thus challenges the common association between sin and rule-breaking. By keeping moral laws, a person can feel entitled to God’s blessings; in this way, they seek to become their own savior and bypass the need for Christ’s grace.
This is the elder brother’s attitude. That his supposed morality is really a form of leverage becomes clear when he retaliates after his brother’s restoration reduces his inheritance, revealing his entitlement over family resources. Keller notes a similar dynamic in Peter Shaffer’s Amadeus. The composer Salieri promises God moral perfection in exchange for fame. However, when he realizes that God gifted superior talent to Mozart, a man Salieri sees as undeserving, he becomes enraged at the perceived injustice. Ultimately, Salieri turns on God and plots Mozart’s destruction, underscoring that he was only ever “obeying” God in an effort to get what he himself wanted: “Soon the moral and respectable Salieri shows himself capable of greater evil than the immoral, vulgar Mozart. While the Mozart of Amadeus is irreligious, it is Salieri the devout who ends up in a much greater state of alienation from God” (48).
Noting that this kind of alienation can be difficult to spot, Keller cites the example of a woman in Christian ministry who realized her despair over a chronic illness stemmed from a subconscious belief that God “owed her.” The key distinction between sin of this kind and genuine obedience is that “elder brothers” are trying to “get things” from God rather than following God’s law to become closer to God. Thus, Keller reiterates, sin is not fundamentally a question of breaking rules; it is the act of usurping God’s place.
The fact that the father loves and welcomes both sons despite their errors shows, for Keller, that the human tendency to see some people as moral and others as immoral is misguided. He argues that this distinguishes the gospel from other spiritual, political, and ethical schema: It declares that “everyone is wrong, everyone is loved, and everyone is called to […] change” (52).
He elaborates that where an “elder brother” judges others in terms of perceived rule-adherence and where a “younger brother” judges others in terms of open-mindedness, Jesus’s division centers on pride. Those who recognize their own shortcomings are closer to God than those who do not. To illustrate this idea, Keller relates an anecdote about Christian writer G. K. Chesterton, who reportedly replied, “I am” in response to a question about what was wrong with the world.
That said, Keller argues, the elder brother’s form of “self-salvation” is more dangerous because it is easier to miss. His state is therefore more desperate; Jesus teaches that mere external observance of religion is not enough, though it is often taken to be.
This chapter formally introduces Keller’s argument about Sin as Self-Salvation. Rebellion against God can manifest as either the younger brother’s flagrant disobedience or the elder brother’s diligent obedience because sin is not inherently about rule-breaking. Rather, it is an attitude toward God that Keller uses the parable to illustrate: Both sons seek to control their father’s resources and displace his authority, demonstrating that sin is fundamentally about putting oneself in God’s place. This is not a new argument. In fact, it is central to much Christian thinking, particularly regarding the origins of humanity’s “fallen” state. It also explains why pride is conventionally viewed as the worst of the deadly sins—because it necessarily precludes openness to God. However, Keller suggests that even many self-described Christians have failed to reckon with this basic precept.
Keller specifically contextualizes this claim within the context of the 21st-century US culture wars, often understood to pit Christians (particularly evangelical Christians) against people of other or no faiths. In fact, he associates the archetypes embodied by each brother—moral conformity and self-discovery—with one side or the other, while acknowledging fluidity on the individual level. Framing these as the only two approaches to politics and to life creates a dichotomy that Keller then breaks in much the same way that (he argues) Jesus’s message itself does. Written primarily for “elder brothers,” Keller’s argument collapses the binary between the religious and “irreligious,” showing that both are lost through the same self-centered motivation. He leans on the parable’s two-act structure, recapitulating it in his own line of argumentation, to underscore this message. The first act affirms the conventional view of sin that Keller’s readers are presumed to hold. However, the second act delivers a pivotal turn meant to jar readers from their complacency. The “good” son’s refusal to enter the feast reveals that his righteousness, not his sinfulness, is the barrier to his father’s love. As in previous chapters, the unresolved ending thus becomes a direct challenge not only to Jesus’s listeners but to Keller’s readers, asking them to consider the elder brother’s choice and their own spiritual state.
The irony with which Chapter 3’s argumentation culminates has much the same effect: The elder brother’s spiritual condition is more perilous than the younger’s, even though the latter’s seems more obvious. In fact, Keller argues, the invisibility of the elder brother’s sin is precisely the problem, as the elder brother feels no need to seek God given his righteousness. This paradox—that morality can be a greater barrier to God than immorality—is Keller’s core critique against legalism and inverts the expectations of anyone who equates religion with following certain moral rules.
Keller continues to use allusions to popular culture to reinforce the immediacy of his claims. For instance, he discusses the characterization of Salieri in Amadeus to show how supposed piety can be a transactional bargain to manipulate God, revealing a heart more alienated than an overt sinner’s. Similarly, the film Witness is used to modernize the two life paths, translating the conflict into a familiar cultural context. This strategy prompts readers to see their own tendencies within these paradigms, preparing them for the critique that Both Brothers Are Lost.



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