Title: The Timeless Struggle: Power, Liberty, and Markets in Political Thought and Outcomes
Throughout history, political and economic debates have revolved around the distribution of power and money. These debates can be organized along a philosophical spectrum ranging from Machiavelli and Tocqueville (0), who emphasize virtue, realism, and institutional control, to Locke and Adam Smith (100), who champion individual liberty, natural rights, and market-driven order. In the middle lie the empiricists and institutionalists like Montesquieu and Hume (around 50), whose predictive frameworks balance normative ideals with pragmatic skepticism. This letter examines key historical epochs to assess the predictive power of these worldviews over short (2-year), medium (10-year), and long (30-year) horizons, using political, military, and economic outcomes as our measuring stick.
We conclude by predicting while Machiavellians win in the now, Humeans rule the decade, and Smithians shape the age. The most predictive thinkers are not those who shout principles but those who measure consequences. For those who disagree, the scores offer a way to choose your own framework based on your historical character of choice.
The cycle continues—but the balance point moves with institutions, technology, and demography. In that sense, Montesquieu and Hume remain the deepest guides—not the loudest, but the most accurate.
Rather than treat these as context-specific, this paper argues for a meta-framework—organizing thinkers and their worldviews on a 0 to 100 scale, from Machiavellian realism (0) to Lockean liberty (100), with Humean skepticism and Montesquieuan balance in between.
The Framework: Philosophical Coordinates
- 0–30 (Machiavelli / Tocqueville): Emphasizes order, hierarchy, virtue, and realism. Values cohesion over liberty.
- 40–60 (Montesquieu / Hume): Institutions, empirical realism, and skepticism toward abstraction. Pragmatic, adaptive.
- 70–100 (Locke / Smith): Focus on liberty, markets, individual rights. Optimistic about spontaneous order and moral progress.
Summary Table: Horizon-Based Sector Framework
| Time Horizon | Focus | Top Sectors | Predictive Lens |
| 2–5 Years | Geopolitics & Realpolitik | Defense, AI/Semiconductors, Oil, Surveillance and Cybersecurity | Machiavelli / Tocqueville |
| 5–10 Years | Strategic Rotation & Repricing | Automation, Utilities, EM Consumer, MedTech | Locke / Smith |
| 20+ Years | Civilizational Builders & Compounders | Water, Green Energy, Education, Data Infra, Biotech | Montesquieu / Hume |
A. Classical and Medieval Worlds (c. 500 BCE – 1500 CE)
- Dominant Viewpoint: Machiavellian-Tocquevillian realism.
- Outcomes: Stability through hierarchy (Rome, feudal Christendom). Economic stagnation but political endurance.
- Predictive Power: High in short and medium term (2–10 years). Low in long term—collapsed under complexity and innovation constraints.
B. Early Modern Europe (1500–1776)
- Emerging Forces: Humean empiricism and Montesquieuan institutional design (British constitutional monarchy).
- Economic Revolution: Mercantilism gives way to Smithian capitalism.
- Predictive Power: Montesquieu/Hume achieve greatest 10–30 year predictions: Britain’s constitutional evolution leads to empire, industrial takeoff.
C. The American Founding (1776–1826)
- Actors:
- Adams, Washington (20–25)
- Hamilton (40), Madison (50), Franklin (65)
- Jefferson, Paine (85–95)
- Outcomes: Constitution as institutionalist compromise. Jefferson’s Lockean ideals inspire revolution but are tempered by Madisonian realism.
- Prediction Accuracy: Hume/Montesquieu centrist view most prescient at 10- and 30-year marks.
D. Industrial and Imperial Ages (1826–1914)
- Dominant Ideas: Smithian capitalism, with growing Machiavellian realpolitik (Bismarck, colonialism).
- Short-Term: Machiavellian empire-building succeeds (Germany, Britain, France).
- Medium-Term: Smithian systems deliver higher economic productivity.
- Long-Term: Montesquieuan frameworks (e.g., U.S. checks and balances) prove most stable and adaptable.
E. 20th Century: Democracy vs Authoritarianism
- Major Events:
- WWII: Machiavellian power states (Nazi Germany, USSR) vs Lockean democracies (U.S., U.K.).
- Cold War: Institutionalist containment wins via long-term resilience.
- Predictive Accuracy:
- Short-term: Realists (e.g., Kissinger, Kennan) make accurate 2-year predictions.
- 10-year: Humean moderation wins (containment, institutional strength).
- 30-year: Smithian liberal order dominates post-Cold War.
F. 21st Century: Fragmentation and Return of Power Politics
- 2000s–2020s: Rise of populism (Trump, Brexit), erosion of institutions, backlash to globalization.
- Machiavellian Surge: Trump, Putin, Xi use statecraft, charisma, nationalism.
- Institutionalist Struggle: EU, U.S. Congress, rule-based systems weaken.
- Markets Adapt: Tech billionaires, decentralized finance rise with Smithian themes.
Key Battlelines:
| Issue | Machiavelli & Tocqueville | Locke & Smith |
|---|---|---|
| Strategic Sovereignty | Vital for survival. Dependency on rivals is suicidal. | Trade interdependence reduces conflict and maximizes utility. |
| Cultural Fragmentation | Lethal to republics. Shared identity is essential. | As long as legal rights are respected, pluralism is acceptable. |
| Elites and Institutions | Naturally self-serving unless constrained. Must be rooted in common experience. | Trust in institutional evolution and rule of law to check elite abuse. |
| Moral Fabric vs. Individual Liberty | Civic virtue and social cohesion outweigh expressive individualism. | Individual liberty is the bedrock of justice and progress. |
| Correcting Liberal Overreach | Requires reasserting national interest, industrial base, and civic identity. | Dangerous—risk of overcorrecting into protectionism and authoritarianism. |
- Machiavelli & Tocqueville: Power, Stability, and Civic Virtue
These two differ in tone (Machiavelli: realist; Tocqueville: democratic moralist), but converge on several fronts when it comes to warning against institutional decay, elite arrogance, and the erosion of civic unity.
Shared Themes:
| Theme | Machiavelli | Tocqueville |
|---|---|---|
| Power & Fragility | Advocates ruthless realism—states must secure power before pursuing virtue. Warns against naivete. | Warns that democratic institutions decay into passivity and tyranny if not anchored by civic virtue. |
| Distrust of Idealism | Scoffs at utopian liberalism; power always rules. Elites who ignore strategic realism invite collapse. | Observes that excessive faith in equality and progress can erode moral independence. |
| Concern for National Cohesion | Praises the Roman republic’s mixed system and citizen-soldiers; detests luxury and division. | Values civil society and local institutions as bulwarks against bureaucratic centralization. |
| Critique of Cosmopolitan Elites | Princes must not delegate power to unaccountable foreign interests. | Elites who isolate themselves from common culture become antidemocratic. |
| Approach to Migration/Fragmentation | Would oppose policies that dilute loyalty to the state. | Warns that democracy cannot survive if shared values vanish or parallel communities form. |
In sum: These thinkers prioritize stability, moral unity, and strategic realism. They’d argue today’s liberal order is failing because it lacks those anchors.
Summary Table
| Thinker | Similarity Score | Primary Alignments | Key Dissonance |
|---|---|---|---|
| Tocqueville | 85/100 | Middle-class erosion, elite capture, DEI critique, civic decay | Risk of overcorrecting into majority tyranny |
| Hobbes | 70/100 | National sovereignty, anti-fragmentation, anti-weakness | Prefers top-down enforcement, not decentralized correction |
| Rousseau | 45/100 | Critique of inequality and alienation | Distrusts nationalism, prefers moral unity over strategic realism |
- Thomas Hobbes (Similarity Score: 70/100)
Core Lens: Order, Security, and Sovereignty. Humans are driven by fear, competition, and glory. Without strong authority (the Leviathan), society collapses into chaos.
Likely Viewpoints:
Globalization and Strategic Dependence: Hobbes would be deeply skeptical. Outsourcing vital industries, hollowing national defense, and relying on adversaries (e.g. China, Russia) contradict the Hobbesian need for sovereign self-sufficiency to avoid anarchy.
DEI and Cultural Fragmentation: He would likely see DEI and identity-based preferences as introducing internal factionalism and undermining the Leviathan’s unity. Anything that pits groups against each other risks civil war.
Migration Pressures: Mass immigration would be perceived as destabilizing if it fractures societal cohesion. For Hobbes, shared allegiance to the sovereign is paramount—cultural incompatibilities would be dangerous.
Correction vs. Collapse: He would support the call for recalibration—but only if done through top-down enforcement, not bottom-up populism. A strong state must force re-industrialization, enforce law and order, and regulate economic dependencies.
Overall: Hobbes would support much of the analysis if implemented through a dominant, central authority that suppresses disorder and enforces national interests.
- Jean-Jacques Rousseau (Similarity Score: 45/100)
Core Lens: Modern civilization corrupts natural man. The ideal state is based on the general will and collective moral unity. Inequality, hierarchy, and artificial institutions distort true freedom.
Likely Viewpoints:
Global Capitalism & Inequality: He would agree that the post-Cold War order led to unnatural inequalities and alienation. Offshoring, wealth concentration, and consumerism reflect his fear that amour propre (vain self-love) has replaced amour de soi (self-preservation and virtue).
DEI and Identity Politics: Rousseau would be critical of DEI as implemented—especially if it’s rooted in bureaucratic policy rather than organic communal will. However, he’d support sincere efforts to reduce systemic domination and give voice to marginalized groups.
Sovereignty and National Autonomy: He’d support the idea of strategic autonomy—but only if it emerges from a participatory, moral society, not elite imposition or fear-based nationalism.
Migration and Cultural Strain: He’d be ambivalent. If migration disrupts collective identity and prevents the formation of a coherent general will, it would be problematic. But he’d oppose xenophobia or nationalism as a solution.
Overall: Rousseau would critique globalization’s moral failings and inequality, but would distrust technocratic or nationalistic solutions that don’t rebuild genuine community or moral unity.
- Alexis de Tocqueville (Similarity Score: 85/100)
Core Lens: Democracy’s strengths and pathologies. Liberty thrives in balanced, decentralized institutions. Equality can become tyrannical if it suppresses individuality and moral responsibility.
Likely Viewpoints:
Hollowing of the Middle Class: He would strongly align with the concern that the middle class—democracy’s foundation—is eroding. He warned that economic centralization and dependency breed soft despotism.
Globalization and Strategic Dependency: He’d view these as elite-driven processes that reduce citizens to passive spectators—dependent on technocratic decisions rather than democratic agency.
DEI and Cultural Fragmentation: Tocqueville would be sharply critical of DEI policies that prioritize group identity over individual virtue. He’d see them as undermining meritocracy and social trust.
Mass Migration: Like with DEI, Tocqueville would support pluralism if assimilation is achievable. But if migration dilutes civic unity or encourages parallel societies, he’d see that as a direct threat to democratic cohesion.
Rise of Nationalism as Corrective: Tocqueville would call this a pendulum swing. He’d worry about overcorrection (majority tyranny), but agree the system needed recalibration—ideally via reinvigorated civic participation and local autonomy.
Overall: Tocqueville would be the most aligned, especially on cultural fragmentation, democratic decay, elite capture, and the need to rebuild social trust and middle-class stability.
Hume’s Position: 65 / 100
Justification:
| Theme | Hume’s View | Alignment | Weight |
|---|---|---|---|
| Skepticism of Rationalist Utopianism | Hume distrusts abstract reason in politics—aligns with Machiavelli/Tocqueville. Institutions emerge from experience, not design. | ~30 | Strong |
| Commerce & Civilized Order | Hume is a strong advocate for commerce, seeing it as a civilizing force that refines manners and reduces violence. | ~80 | Strong |
| Custom & Tradition | He emphasizes the role of custom and habit in preserving order, aligning with Tocqueville’s view on civic religion and institutions. | ~40 | Moderate |
| Moderation in Political Change | Believes in gradual evolution of government and is suspicious of both revolution and rigid conservatism. | ~60 | Moderate |
| Moral Sentiments & Institutions | Thinks stable government and property rights emerge from shared moral sentiments, not natural law. Less individualistic than Locke. | ~50 | Strong |
| National Sovereignty & Elites | Not Machiavellian—he is urbane and detached. Trusts elites if institutionalized but warns against abstract ideology in ruling. | ~55 | Light |
Hume = 65/100
He believes in commercial liberalism, practical liberty, and institutional evolution, but not rationalist utopia or cosmopolitan overreach. Closer to Smith than Locke, but suspicious enough of liberal excess to sit within Tocqueville’s gravitational pull.
Montesquieu’s Position: 45 / 100
Justification:
| Theme | Montesquieu’s View | Alignment | Weight |
|---|---|---|---|
| Liberty Through Structure | Believes liberty is secured not by rights alone, but by a complex structure of institutions that balance power—legislative, executive, judicial. | ~60 | Strong |
| Virtue & Civic Character | Argues that different regimes require different virtues (e.g., moderation in monarchies, public virtue in republics). Strongly aligned with Tocqueville on moral prerequisites. | ~30 | Strong |
| Cultural & Historical Relativism | Advocates for understanding laws in the context of climate, geography, history—a highly empirical, realist stance. | ~20 | Strong |
| Fear of Despotism | Sees despotism as the greatest danger—aligns with Locke in protecting liberty through separation of powers. | ~70 | Moderate |
| Commerce & Softening of Manners | Believes commerce “polishes and softens barbaric ways” but doesn’t fully trust it to generate civic virtue—closer to Smith than Machiavelli, but cautious. | ~60 | Moderate |
| Skepticism of Rational Universalism | Doesn’t believe in “one best system.” Laws must fit the people. Deeply Tocquevillian in that sense. | ~25 | Moderate |
Bottom line:
Montesquieu = 45/100
He values liberty, but sees it as the product of institutional design, not ideology. Sits nearly at the midpoint—Lockean in goals, Tocquevillian in method, and mildly Machiavellian in realism.
Hume & Montesquieu:
Hume’s incrementalism and skepticism toward radical change suggest that sectors which embody gradual, stable growth will perform well. Montesquieu’s emphasis on institutional balance and the importance of laws reflecting geography, culture, and climate indicates that sectors benefiting from sound institutions and regulatory stability will thrive in the long run.
- Sectors Likely to Outperform:
- Infrastructure & Real Estate: With increasing urbanization, the demand for robust infrastructure and sustainable real estate will rise. Hume’s belief in gradual adaptation points to the need for stable, long-term investments in these areas.
- Education & Research: Long-term investments in human capital, particularly through technology-enabled education platforms and research institutions, are likely to be highly productive.
- Healthcare (Aging Populations): In developed nations, the aging population will drive demand for long-term healthcare services. The healthcare sector will continue to grow steadily as it adapts to the needs of an older demographic.
- Green Technology and Environmental Solutions: While renewable energy may have short- to medium-term momentum, Hume and Montesquieu’s emphasis on stability and long-term institutional sustainability suggests green technologies like carbon capture and sustainable agriculture will have lasting impacts.
- Neglected or On-Sale Sectors:
- Agriculture & Food Production: As the global population increases, the demand for food production will rise, leading to a long-term investment opportunity in agriculture. The slow-to-change nature of this industry makes it undervalued compared to tech sectors but very necessary in the context of global growth.
- Water & Resource Management: With climate change and population pressures, the management of global water resources will become increasingly important. Long-term investments in water purification and resource management will be crucial.
Major Founders by Placement
Grouped by Camp
Machiavelli / Tocqueville (0–30)
- John Adams
- George Washington
- John Jay
Hume / Montesquieu (40–60)
- Alexander Hamilton (leaning Machiavellian)
- James Madison (true institutional center)
- Benjamin Franklin (leaning Lockean)
Locke / Smith (70–100)
- Thomas Jefferson
- Patrick Henry
- Thomas Paine
| Founder | Score | Justification |
|---|---|---|
| John Adams | 15 | Deeply republican, virtue-driven, suspicious of democracy, feared mob rule. Admired Cicero and Machiavelli. Closest to the Machiavelli/Tocqueville camp. |
| George Washington | 25 | A civic-republican hero figure. Believed in duty, honor, stability. Skeptical of factions and excess liberty. Taciturn but strategic—very Roman/Machiavellian. |
| James Madison | 50 | The great institutionalist. Architect of checks and balances, inspired by Montesquieu. Recognized human nature’s flaws like Hume but designed around them. |
| Alexander Hamilton | 40 | Wanted a strong executive, central banking, manufacturing power—realist and power-conscious. Admired British constitutional monarchy. Less about liberty, more about order and strength. |
| Thomas Jefferson | 85 | The radical Enlightenment figure. Lockean to the core: natural rights, minimal government, agrarian liberty. Distrusted central authority. |
| Benjamin Franklin | 65 | A practical Smithian. Pro-commerce, science, pluralism, compromise. Believed liberty was essential but supported institutions to maintain it. |
| Thomas Paine | 95 | Almost pure ideology: rights, anti-monarchy, revolutionary. Closer to French Enlightenment than the American institutionalists. Would be very comfortable with modern libertarians. |
| John Jay | 35 | Conservative realist, order-first. Elite-focused Federalist. Believed in stable institutions and social hierarchy. |
| Patrick Henry | 90 | “Give me liberty or give me death.” Radical decentralist, anti-Federalist. Distrusted consolidated power. Similar to Paine in attitude. |
Additional Insights
- The Constitution itself is more Montesquieuan/Humean—an empirical, cautious design built for a flawed humanity.
- The Declaration of Independence is more Lockean—abstract, idealistic, asserting rights and principles.
- Federalists (Hamilton, Jay, Adams) were institutional realists—wanted strength and order.
- Anti-Federalists (Jefferson, Henry, Paine) feared tyranny and wanted decentralized liberty.
The Founders in Retrospect
- Adams/Washington: Right about need for civic virtue—but underestimated individualism.
- Hamilton/Madison: Most accurate at 10–30 year mark. Designed a system that endured.
- Jefferson/Paine: Visionary but often destabilizing in the short run.
I. Tactical Alpha (2–5 Year Horizon)
Philosophical Lens: Machiavelli and Tocqueville (Score: 70–100) — Short-term geopolitical realism. Predictive strength: high over 2–5 years. Effective during transitional periods (wars, elections, social instability). Focused on regime behavior, state incentives, elite competition, and populist responses.
| Sector | Strategic Rationale |
|---|---|
| Defense & Aerospace | Power projection, rearmament cycles, NATO expansion. Tocqueville’s democratic anxiety reinforces state militarism. Machiavelli would see defense contractors as “arms of the prince.” |
| Semiconductors & AI Infrastructure | Technology arms races and state-subsidized industrial policy. Reflects Machiavellian focus on securing strategic advantage. |
| Cybersecurity | The new battlefield. Modern fortresses. Ideal for Tocqueville’s decentralized threat environments and Machiavellian deception. |
| Oil, Uranium, Copper | Resource realism as energy independence trumps climate virtue. Shortage + geopolitics = tactical edge. |
| Specialty Insurance & Reinsurance | Mispriced risk due to complexity or novelty (climate, cyber, contagion). A Machiavellian edge: know what others misprice. |
II. Strategic Value (5–10 Year Horizon)
Philosophical Lens: Locke and Adam Smith (Score: 0–30) — Enlightenment liberalism. Predictive strength: medium-high in peaceful, stable jurisdictions. Strong during post-disruption recovery and global reintegration phases. Centers on free markets, property rights, innovation.
| Sector | Strategic Rationale |
| Industrial Automation & Robotics | Market-based solutions to labor scarcity, reshoring. Locke’s productive property meets Smith’s efficiency gains. |
| Utilities & Grid Infrastructure | Mispriced due to macro headwinds (rates), but essential. Smith: steady demand meets latent underinvestment. |
| Maritime Logistics | Global trade’s foundation. Beneficiaries of bottlenecks + reinvestment. Smithian competition within high-barrier industries. |
| Emerging Market Consumers | Middle-class expansion via market liberalization. Locke would see property growth, Smith would see specialization dividends. |
| Diagnostics & MedTech | The invisible compounder: innovation without the biotech volatility. Liberal knowledge systems made visible. |
III. Structural Compounders (20+ Year Horizon)
Philosophical Lens: Montesquieu and Hume (Score: 40–60) — Institutional gradualism and systemic balance. Predictive strength: very high in slow-moving but compounding domains. Best in post-consolidation phases of civilizational renewal.
| Sector | Strategic Rationale |
| Water Infrastructure & Purification | Non-negotiable long-term need. Montesquieu’s civil equilibrium demands it. |
| Green Energy Ecosystem | Decades-long convergence around renewables. SMRs, grid storage, Humean probabilistic evolution. |
| Education Tech & Credentialing | Institutions redefined by tech. Montesquieu: a new equilibrium of authority and liberty. |
| AgriTech & Bioengineering | Evolutionary pressure on food systems. Hume’s emphasis on adaptation and feedback loops. |
| Data Infrastructure | Cloud, fiber, AI stack = infrastructure of 21st-century civilization. Permanent utility. |
| Longevity & Neuro Biotech | Temporal outliers, moral economies. Hume would view these as stochastic long-term payoffs. |
Investment Allocation Strategy by Horizon (Top 0.1% Investors)
Assume discretionary assets of $10M–$100M, with net income $1M+. Use philosophy-aligned portfolios to preserve optionality and compounding power:
| Horizon | % Annual Allocation | Rationale |
| 2–5 Years | 15–25% | High-conviction tactical bets. Partner with regime-aligned funds or private thematic opportunities. Tactical risk, high alpha. |
| 5–10 Years | 25–35% | Strategic pricing dislocations, concentrated conviction. Misunderstood assets with tailwinds. Combine public and private equity. |
| 15 Years | 35–45% | Hybrid allocation. Lockean market bets + Humean compounding. Energy, education, automation. Blends agility with compoundability. |
| 20+ Years | 30–50% | Deep time bets on civilizational infrastructure. Direct investments, venture exposure, family office plays. Highest optionality. |