By: Maha Khan-Ahmad

For Sheldon Zeiger, J.D., the practice of law has always been about more than documents, transactions, and courtroom disputes. An estate planning attorney who has specialized in the field since 1985, and a practicing Certified Financial Planner for 40 years, Zeiger has spent decades examining how wealth is created, protected, transferred and, ultimately, taxed.

Today, that professional experience informs a broader intellectual project: an exploration of capitalism, inequality, regulation and the ideas of the economists and moral philosophers who helped shape modern economic thought.

Zeiger, whose Chicago law practice focuses on estate planning as well as corporate, securities and transactional matters, argues that one of the most persistent misunderstandings about capitalism begins with a misunderstanding of Adam Smith.

At the center of his argument is Smith’s famous concept of the “invisible hand.”

Zeiger rejects the popular interpretation that the invisible hand simply means individuals pursuing their own interests somehow automatically produce the best outcomes for society.

Instead, he sees something more fundamentally reciprocal.

“It is in my self-interest to provide goods and services that benefit others,” Zeiger said.

In his interpretation, economic exchange is rooted in a form of practical empathy: A business succeeds because it provides something another person values. The consumer benefits, and the business benefits in return.

“That’s how our whole economy works,” he said.

Beyond the Textbook Version of Adam Smith

Zeiger’s interpretation of Smith is heavily influenced by the relationship between Smith and fellow Enlightenment thinker David Hume. He points to Dennis C. Rasmussen’s The Infidel and the Professor, a book about the friendship between Hume and Smith, as an important source for his understanding of their intellectual relationship.

For Zeiger, Smith’s The Theory of Moral Sentiments is particularly important.

Published decades before The Wealth of Nations, the work examined how human beings develop moral judgments and respond to the experiences of others. Zeiger argues that Smith’s economic thinking cannot be separated from these earlier questions about morality, empathy and human behavior.

“Theory of Moral Sentiments is really his real preeminent work,” Zeiger said, describing it as closer to psychology and moral philosophy than conventional economics.

That distinction, he argues, matters when interpreting Smith’s views on markets.

Zeiger contends that Smith and Hume were writing in a world already shaped by powerful institutions, including the monarchy, the church and large trading companies, and therefore should not simply be retroactively portrayed as advocates of an entirely unregulated marketplace.

His conclusion is that the historical context surrounding Smith’s work is essential to understanding what the economist actually meant by markets and economic freedom.

Who Benefits From Laissez-Faire?

That question leads directly into Zeiger’s skepticism about modern interpretations of laissez-faire capitalism.

He argues that large corporations have an interest in minimizing regulatory constraints and that political influence can become another component of the economic system.

His concerns are informed by his own early career in securities law.

As a young law clerk, Zeiger said he spent considerable time reading the securities documents he was tasked with delivering and filing. He recalled noticing that many of the disputes involved situations in which customers had given financial professionals discretionary authority over their accounts.

Years later, after returning from Dallas, he became an in-house compliance officer for a Futures Commission Merchant at the Chicago Mercantile Exchange.

By then, he said, the industry had moved toward mandatory arbitration agreements for customer disputes.

For Zeiger, that experience raised a fundamental question about the relationship between self-regulation, government oversight and individual consumers.

His broader argument is that regulation cannot be understood separately from the economic interests of the organizations being regulated.

A Lawyer’s View of Capitalism

Zeiger describes capitalism as a “living organism,” a system capable of producing extraordinary growth while also generating unintended consequences.

He is particularly interested in small businesses.

Rather than focusing primarily on publicly traded corporations, Zeiger sees small and midsize businesses as the part of the economy most closely resembling the decentralized economic activity described by classical economic thinkers.

His own practice reinforces that perspective.

Since 1995, Zeiger has specialized in estate planning, helping clients develop wills, trusts, healthcare and property powers of attorney, and beneficiary designations. His broader legal experience includes corporate transactions, contracts, business sales, compliance and securities matters. He also brings a finance background, having worked as a practicing Certified Financial Planner for 30 years, experience he says gives him a grounding in economics.

That professional background gives him a particularly close view of how wealth moves from one generation to another.

And it is here that his philosophical questions become intensely practical.

The Wealth-Transfer Question

Zeiger believes one of the central economic challenges facing the United States is the concentration of wealth.

But he does not argue that everyone must have the same amount of wealth.

“I’m not egalitarian,” he said. “I don’t feel like you need to be equal.”

Instead, he focuses on what he calls utility: whether people have access to basic necessities such as food, housing, and education.

That perspective leads him to question whether wealth redistribution alone can address structural inequality.

He points instead toward policies and market mechanisms that, in his view, would put more purchasing power into the hands of consumers and small businesses.

He also points to the inheritance system as an important part of the discussion.

As an estate planning attorney, Zeiger is familiar with the tax rules governing the transfer of assets at death, including the step-up in basis. Under U.S. tax law, inherited property generally receives a tax basis equal to its fair market value at the owner’s death, subject to applicable rules and exceptions.

For Zeiger, the significance extends beyond tax planning.

Estate planning, he argues, is one of the mechanisms through which accumulated wealth can remain concentrated across generations.

That makes his own profession an unusual vantage point from which to examine inequality.

“I’m basically the person who works in this area,” he said. “I’m a professional trustee.”

Looking Below the Official Economy

Zeiger’s interests also extend beyond traditional measures of economic activity.

He is fascinated by what he calls the “underground economy,” economic activity that occurs outside formal or regulated markets.

His argument is that whenever governments prohibit or heavily regulate an activity, economic activity can migrate outside the formal system.

He points to the evolution of the marijuana industry as an example of an economic sector moving, at least in part, from an illicit market into regulated commerce.

For Zeiger, this illustrates capitalism’s adaptability.

The market, in his view, continually responds to incentives, restrictions, and opportunities. Trying to suppress one form of economic activity can create another.

He acknowledges that underground markets can involve serious problems, but sees their existence as evidence of how difficult it is for any institution to completely control economic behavior.

From Estate Planning to Economics

At first glance, the connection between estate planning and Smith’s moral philosophy might seem unusual.

For Zeiger, however, the connection is straightforward.

Estate planning is ultimately about what happens to wealth after it has been created. Corporate and securities law provide another view into how businesses operate and how regulation affects markets. Business planning offers yet another perspective on how entrepreneurs seek capital and respond to market conditions.

Taken together, those experiences have led Zeiger to think about capitalism less as an abstract economic theory and more as an evolving system of human behavior.

That is also why he is reluctant to reduce the conversation to a simple debate between capitalism and Marxism.

Instead, he says he is interested in finding useful ideas wherever they originate.

“I want to get the best ideas from everywhere,” he said.

The Questions Zeiger Wants to Keep Asking

His approach is intentionally exploratory.

He frequently combines ideas from economics, philosophy, law, history, and his own professional experiences, looking for connections that might lead to a new way of understanding familiar problems.

That includes questions about wealth concentration, corporate power, regulation, inheritance, consumer purchasing power and the informal economy.

It also explains why Zeiger describes his public commentary as somewhat unconventional.

He is not necessarily trying to produce a definitive theory of capitalism. Rather, he wants to provoke questions and then investigate the answers.

For someone who has spent his career helping individuals and families protect and transfer their assets, the questions are not merely academic.

They are embedded in the work itself.

Every will, trust, business transaction, and estate plan is part of a much larger economic story: who creates wealth, who controls it, who benefits from it, and what happens when it moves from one generation to the next.

For Zeiger, understanding that story requires going back to the thinkers who first asked how markets and morality intersect.

And it requires looking beyond the familiar textbook version of the invisible hand.