Balls and Strikes

Nobody is above the fray. You can't understand the present without understanding the past.

A while ago, I observed a tweet from Jason Calacanis, a Venture Capitalist and central figure of the All-In Podcast, who promised to fairly evaluate the Trump presidency as it unfolded.

I think a lot of people appreciate this stance, because on the surface it appears to be fair and reasonable. It suggests that he is engaging in some intellectually honest refusal to pre-judge the Trump presidency. But I am going to suggest that this kind of stance is nothing short of a form of wayward amoralism.

I don't mean to single Calacanis out here—I have close friends who take this same position. Indeed, this stance seems to be increasingly infectious throughout the business world, adopted for obvious reasons as America appears to be lapsing toward oligarchy. The phenomenon is much broader and more significant than any individual's position.

This “calling balls and strikes” approach to political commentary represents something far more troubling than just an unfortunate metaphor—it reveals a fundamental misunderstanding of how political accountability operates in a democratic society. By suggesting we can evaluate each action in isolation, divorced from context and history, this framework actively undermines our ability to maintain coherent moral and political judgment.

What we're witnessing is a form of intentional amnesia by someone who wants to remain relevant no matter which way the wind blows. This isn't accidental forgetfulness—it's a calculated strategy that allows Calacanis to maintain influence across political divides without taking genuine moral stands. Like a weathervane responding to each new breeze without memory of previous directions, this framework enables continuous repositioning without acknowledging past positions or cumulative patterns.

Consider what this approach asks us to ignore. When Trump announces a new business venture, the “balls and strikes” framework would have us evaluate it as an isolated incident, completely separate from his history of business practices, his pending legal challenges, or his simultaneous pursuit of the presidency. This isn't neutrality—it's a form of intentional amnesia that serves to obscure patterns of behavior that are crucial for democratic accountability.

The baseball metaphor fails fundamentally because democracy isn't a sport with cleanly separated plays. Political actions don't exist in isolation—they build on each other, create precedents, and shape institutions. Each decision exists within a complex web of past actions, established patterns, and future implications. By pretending we can evaluate each action as an independent “pitch,” we engage in a moral abdication that makes genuine accountability impossible.

The spread of this position throughout the business world is particularly telling. As America appears to drift toward oligarchy, the appeal of moral flexibility becomes obvious. Business leaders increasingly find themselves navigating a landscape where political power and economic opportunity are increasingly intertwined. The “balls and strikes” framework provides perfect cover—it looks like principled neutrality while actually representing a strategic adaptation to growing oligarchic tendencies.

This false neutrality is particularly dangerous because it presents itself as objective analysis while actually performing a subtle form of historical erasure. When we treat each action as if yesterday didn't happen, we make it impossible to identify patterns of behavior or hold leaders accountable for cumulative actions. It's akin to evaluating a marriage based on single interactions while ignoring years of accumulated trust or betrayal.

What makes this approach particularly insidious is how it coopts the language of data-driven analysis and objectivity to justify what amounts to moral surrender. By leveraging the business world's preference for discrete, quantifiable metrics, it creates a pseudo-scientific veneer for what is essentially moral cowardice. This isn't fairness—it's a strategic positioning that allows its practitioners to never be wrong in retrospect because they're constantly resetting the scoreboard.

The “balls and strikes” framework also fundamentally misunderstands how democratic institutions function. These institutions don't reset each day like a new baseball game—they carry the weight of precedent, tradition, and accumulated damage or strength. When we pretend each action can be evaluated independently, we blind ourselves to how institutional decay occurs through the steady accumulation of seemingly minor violations.

The solution isn't to abandon attempts at objective analysis, but to recognize that true objectivity requires understanding context and patterns. We need frameworks that can account for how political actions build on each other, how institutional damage accumulates, and how patterns of behavior matter more than isolated incidents. Most importantly, we need to recognize that moral judgment requires maintaining historical memory—something the “balls and strikes” approach actively works against.

The stakes of this discussion extend far beyond metaphorical preferences. How we frame political analysis shapes our ability to maintain democratic accountability and protect institutions. When we accept frameworks that erase history and context, we make it impossible to understand—let alone prevent—democratic decay. What presents itself as reasonable neutrality is actually a calculated adaptation to growing oligarchic power, an abdication of the moral responsibility that citizenship in a democracy demands.

This matters precisely because we're witnessing a broader transformation of American society. As economic power concentrates and traditional democratic institutions weaken, the business community's approach to political evaluation becomes increasingly consequential. The “balls and strikes” framework isn't just a rhetorical choice—it's a symptom of and contributor to democratic erosion, a way of normalizing the accumulation of anti-democratic behavior by pretending each instance can be evaluated in isolation from the pattern it creates.

George Santayana’s famous quote—sometimes apocryphally credited to Edmund Burke—applies here, “Those who cannot remember the past are condemned to repeat it.” Burke however did say something on this point, when he said, “people will not look forward to posterity who never look backward to their ancestors.”

The implications of this framework run deeper than mere political positioning. As the philosopher Hannah Arendt observed, evil often advances not through dramatic violations but through the accumulated effect of seemingly routine decisions by people who refuse to see patterns or take moral stands. The “balls and strikes” framework doesn't just fail to resist this process—it actively enables it by training us to see each action as isolated and routine, divorced from any pattern or accumulation. For as we might say, “those who encourage us to forget the past only serve the demons of cynicism.”

This cynicism masquerades as sophistication. The framework presents itself as mature realism—suggesting that treating each action in isolation is somehow more “objective” than maintaining historical memory. But this supposed realism is actually a form of moral surrender. It makes resistance to institutional decay seem naive while presenting cynical acceptance as wisdom. When business leaders treat each political action as an isolated incident, they're not just choosing personal convenience—they're promoting a worldview where moral judgment itself becomes impossible.

James Madison understood that if men were angels, no government would be necessary. The whole point of constitutional democracy is to create systems that account for patterns of behavior and accumulated power. When we pretend each action can be evaluated in isolation, we abandon this fundamental insight about how power operates and must be constrained.

Martin Luther King Jr., writing from Birmingham Jail, criticized those who preferred a “negative peace which is the absence of tension to a positive peace which is the presence of justice.” The “balls and strikes” framework similarly prioritizes the appearance of neutrality over the maintenance of democratic accountability. It offers a kind of negative objectivity—the absence of judgment—rather than the positive objectivity that comes from carefully evaluating actions in their full context.

The “balls and strikes” framework offers business leaders a way to navigate increasingly turbulent political waters without taking moral stands that might limit their future options. But this pragmatic flexibility comes at the cost of democratic accountability. What we need instead is the courage to maintain historical memory, to recognize patterns, and to make moral judgments that account for cumulative effects—even when doing so might cost us something in the moment. For in the end, democracy depends not just on our institutions but on our willingness to defend them by maintaining moral clarity in the face of convenient cynicism.