Recently I was listening to an episode of The Grey NATO, a podcast focused on “adventure, travel, diving, driving, gear … and most certainly watches”. The hosts fielded a question from a listener who expressed some discomfort with IWC’s Big Pilot’s watch because of its associations with World War II and its development for the German Luftwaffe.
There is no ready-made answer. The discomfort is legitimate, but as the hosts noted, the meaning of products and brands is not fixed in time. Context shifts. As an analogy, they pointed to Volkswagen, a company whose origins are inseparable from the Nazi regime, yet whose Beetle became, by the 1960s, a symbol of counterculture. The same object can carry radically different meanings, separated only by time, memory, and consumer reinterpretation.
Putting on my brand strategist hat, this discussion raised a broader and more interesting question: what exactly do brands owe us when their histories are compromised? Luxury brands in particular trade not just in function, but in narrative. They tell stories. When those narratives intersect with authoritarian regimes, fascist aesthetics, or extremists, the issue is no longer just historical trivia. It becomes a matter of brand strategy, reputational risk, and consumer psychology.
What discomfort over the IWC Big Pilot ultimately exposes is not a niche uneasiness among some watch collectors, but a broader strategic dilemma. Brands endure longer than moral consensus, and the longer they last, the more ethically complex their inherited meanings become.
The Core Problem: Brands as Long-Lived Moral Containers
Brands are not just commercial identifiers; they are repositories of meaning that accumulate over time, whether curated or inherited. Unlike products, which can be discontinued, or executives who can be replaced, brands persist across political regimes, cultural revolutions, and moral recalibrations. This longevity is usually framed as an asset. We see that in their marketing, which references terms such as “heritage,” “authenticity,” and “legacy”. But all this comes with a cost. Brands inevitably absorb the ethical residue of the eras in which they operated.
This is why uncomfortable histories have a way of resurfacing. A watch originally designed for military aviation, a car company founded as a state project of the Third Reich, or a fashion house that manufactured uniforms for a fascist regime may spend decades reinventing itself, only to find that those origins still shadow them. The question is not whether these associations exist, but how much interpretive control a modern brand actually has over them. Volkswagen demonstrates one possible outcome: mass adoption, generational turnover, and radical recontextualization diluted its origins to the point that the brand’s founding ideology became historically relevant but culturally inert.
Other brands have had a harder time achieving that distance. Hugo Boss, whose ties to Nazi uniform production are well-documented, pursued a long strategy of silence and aesthetic reinvention, betting that high fashion’s forward momentum would outrun historical scrutiny. That bet largely worked until it didn’t, resurfacing periodically in media retrospectives and consumer debates. Similarly, Ford Motor Company cannot fully escape the shadow of Henry Ford’s antisemitism and documented admiration of Nazi leadership, even as the modern company bears little resemblance to its founder. Likewise, Chanel has faced renewed scrutiny in recent years after a docudrama highlighted Coco Chanel’s collaboration with Nazi intelligence during World War II.
From a brand-strategy perspective, the underlying problem is structural. Brands are expected to project coherence and continuity, but moral judgment is discontinuous. A heritage narrative that once conveyed gravitas can suddenly appear compromised. Worse, attempts to aggressively disavow the past can backfire, drawing renewed attention to precisely what the brand hopes to neutralize. The result is a strategic paradox. Acknowledgment risks amplification, while silence risks indictment.
How Can Brands Deal With Negative Historical Legacies?
This is why legacy brands facing morally compromised histories rarely find a clean resolution. Instead, they manage a portfolio of risks — reputational, cultural, and commercial — making calculated decisions about what to emphasize, what to abstract, and what to let fade quietly. The IWC Big Pilot sits squarely in the middle of this dynamic. It is not about whether the watch is “acceptable,” but about how much historical meaning a brand can responsibly carry before its past begins to overwhelm its present.
When brands confront uncomfortable histories or unwanted ideological associations, their responses tend to fall into a small number of recognizable strategic patterns. Some pursue recontextualization, allowing new audiences and cultural meanings to overwrite earlier ones. This is what Volkswagen ultimately did when a car conceived under the Third Reich became, decades later, an emblem of countercultural freedom. Others opt for silence and distance, declining to foreground the past and betting that aesthetic reinvention or sheer forward momentum will outrun historical scrutiny. A smaller number choose explicit reckoning, publicly acknowledging and condemning past entanglements in an effort to align themselves unmistakably with contemporary values. Still others attempt design abstraction, stripping products of overt historical references while preserving their functional or formal essence. Each of these approaches represents not a moral stance so much as a redistribution of reputational risk.
What ultimately separates these strategies is not virtue but tolerance for exposure. Legacy brands do not get to choose whether history matters; they only get to choose when and on whose terms it resurfaces. For luxury brands in particular, because their value rests on symbolism, storytelling, and the promise of meaning beyond utility, history can not be fully neutralized without also diminishing the product itself. Attempts to sanitize the past too thoroughly risk stripping the brand of depth. Yet ignoring it also risks reputational damage. In this sense, historical discomfort is something that cannot be engineered away, but is a structural feature of long-lived brands — one that neither the brand nor the consumer can entirely opt out of.
When Extremists Adopt a Brand (Without Permission)
A different, and often more destabilizing, problem arises when brands acquire toxic associations not through their origins, but through unwanted adoption by extremist movements. In these cases, the brand is not inheriting historical baggage so much as being conscripted into a contemporary ideological performance. This dynamic was explored in a widely discussed article in The Guardian, which examined how some fashion labels have found their products embraced by white supremacist or fascist subcultures. The brands did not design for these audiences, nor did they court them. Examples include companies such as shoemaker New Balance, and Fred Perry’s signature black and yellow polo shirts, products adopted by extremists as a uniform.
From a brand-strategy standpoint, this is a far more volatile scenario than compromised origins. History, however uncomfortable, is finite; extremist appropriation is active, adaptive, and often deliberately provocative. These groups select brands precisely because of their ambiguity. This permits taking certain heritage aesthetics such as militaristic silhouettes, or associations with “order,” “discipline,” or “authenticity” and reframing them to signal ideological belonging.
A brand’s strategic response options narrow quickly. No response becomes a statement in and of itself, as the absence of repudiation can be read as tacit permission. Explicit denunciation may alienate core customers who resent political messaging, while a mere quiet distancing risks allowing the association to metastasize unchecked. Worse, aggressive condemnation can perversely strengthen the extremist attachment by conferring attention and legitimacy, perhaps proving that the brand is symbolically potent enough to provoke outrage. In these situations, brands often resort to indirect tactics such as discontinuing specific items, altering cuts or colorways, or subtly shifting marketing imagery to deprive extremists of the semiotics they find useful. The goal is not moral purification, but symbolic starvation.
What these cases reveal most clearly are the limits of brand sovereignty. Companies like to imagine themselves as stewards of meaning, but extremist adoption demonstrates that meaning is ultimately negotiated in public, not owned. Once a product becomes a symbol, it can be misused as easily as admired. For consumers, this creates a different kind of discomfort than historical association: not guilt by inheritance, but unease at sharing symbolic space with people whose values they reject. And for brands, it suggests the loss of narrative control is not an anomaly but a recurring cost of cultural relevance.
The Consumer’s Role: Ethical Consumption or Symbolic Anxiety?
At some point, debates about compromised brands stop being about corporate intent and start revealing something about the consumer. When a buyer hesitates over a watch, a jacket, or a car because of its historical or ideological associations, the discomfort is rarely about direct harm. No one is materially injured by the purchase itself. Instead, the unease is symbolic. Luxury goods, in particular, function as outward-facing statements of identity, taste, and values. To wear or use them is to participate, however lightly, in the meanings they carry. The question, then, is not simply whether a product is ethical, but whether it feels morally acceptable in public.
This helps explain why collectors and enthusiasts often grapple with these issues more intensely than mass consumers. For example, watch collectors often buy based on narratives. Provenance, heritage, and backstory are not peripheral. They are part of the object’s value proposition. That same sensitivity, however, creates a paradox. The more meaning a consumer demands from an object, the harder it becomes to ignore the meanings they would prefer not to inherit. What looks like ethical concern can sometimes function as a form of symbolic hygiene, which is basically an attempt to keep one’s personal aesthetic uncontaminated by histories or associations that feel socially or psychologically uncomfortable.
How this product scrutiny is applied differs. Few people question the moral genealogy of everyday goods with the same rigor they apply to luxury purchases. This suggests the anxiety is less about ethics in the abstract and more about visibility. We worry most about the objects that are seen, discussed, and interpreted by others. In that sense, ethical consumption is not purely altruistic; it can also be relational. It reflects a concern about what owning or displaying a brand says about us, and how much interpretive ambiguity we are willing to tolerate.
Ultimately, consumers play a role in sustaining or dissolving these associations. Brands can manage narratives, but they cannot compel forgiveness, indifference, or outrage. Each purchase becomes a small act of negotiation between appreciation and discomfort, enjoyment and awareness. The unresolved tension is not a flaw, but a feature. If brands are long-lived moral containers, then consumption is never neutral, but neither is it fully governed by moral clarity. It exists instead in a gray zone where history, identity, and desire overlap, and where the line between principled refusal and symbolic anxiety is rarely as clean as we would like to believe.
Conclusion: No Brand Is Innocent, Only Better Managed
The key lesson from these examples is not that certain brands are uniquely tainted, but that longevity itself is morally hazardous. Any brand that survives wars, regime changes, and cultural revolutions will eventually accumulate associations that do not align with contemporary values. The problem, then, is not the presence of historical baggage, but the illusion that it can be fully shed. Brands do not outlive history; they carry it forward, selectively emphasized or quietly buried, but never entirely erased.
From a strategic standpoint, the most resilient brands are not those that claim moral purity, but those that understand the limits of narrative control. Recontextualization, silence, reckoning, and abstraction are tools, not solutions. What distinguishes effective brand management in these cases is not ethical perfection, but moral literacy. Brands must have a clear-eyed understanding of which histories still exert symbolic force, which can be allowed to recede, and which will inevitably return at moments of cultural sensitivity. Misjudging that balance by over-sanitizing or by ignoring the issue entirely will inevitably invite reputational risk.
For consumers, the implication is also uncomfortable. To engage with legacy brands is to accept a degree of historical ambiguity. Refusal may feel principled and acceptance may feel complicit, but both often reflect a tacit recognition that meaning is layered rather than absolute. The IWC Big Pilot discussion is not really about a watch, just as controversies over cars, clothing, or logos are rarely about utility. They are about how much unresolved history we are willing to live with in the objects we choose to value.
In the end, neither brands nor consumers are granted the luxury of innocence. What remains is management of narratives, of symbols, and of discomfort. The more practical approach is not to ask whether a brand’s past disqualifies it, but whether its present strategy acknowledges that past intelligently, without surrendering either to denial or to paralysis. In a marketplace built on memory as much as design, that may be the only sustainable path forward.