TALKING TAXES IN MILWAUKEE

OP-ED published in the Milwaukee Sentinel May 1, 2025

By Justin Schein

We are deeply divided as a country. The right blames big government and regulation for stifling innovation, while the left believes inequality and greed are hampering social mobility.

At the center of this conflict is the unsexy issue of taxes. But taxes are at the core of who we are as a nation: our economic priorities, our vision of the role of government, even our moral choices are deeply impacted by our tax policy. And while these battles have long been waged on Capitol Hill, and in the media, they have also been happening for decades at my family’s dinner table, between my father and me.

My Dad lived the American Dream. He grew up during the Depression, the youngest son of garment workers, and went from sharing a bed with his brother in Brooklyn to being the President of Sony America living on Park Avenue. Thanks to his service in the Navy at the end of World War II, he earned a degree at NYU, followed by Harvard Law School, both paid for by the GI Bill — a program that not only educated a generation of (mostly white) Americans, but also provided loans for them to buy homes, start families, and build a foundation of generational wealth. 

Dad’s career path was meteoric and along the way, he was determined to save and invest so that his young family didn’t have to face the insecurity he endured as a child. Thus, he began to build an estate plan, carefully managing his finances and taxes, within the bounds of the law, as so many people rightfully do.

Estate tax started under President Theodore Roosevelt

A big part of that involved avoiding the estate tax, a levy on assets left behind at death, instituted by President Theodore Roosevelt to address massive wealth inequality and its detrimental effect on American democracy. It was intended to impact only the richest Americans, and for many years, it did. But by the end of the chaotic 1960s, inflation began to rise, causing the estate tax to affect more and more families.

Reagan’s landslide victory in 1980 ushered in an era of top-down tax cuts as part of trickle down, or “supply side,” economics, which slashed the estate tax rate and increased the amount that was exempt. And my dad, once a New Deal Democrat, was enthusiastically onboard. 

As Dad began to think about retirement in the late ’80s, the political battle over the “death tax,” as its foes dubbed it, began to heat up. Many, like my dad, saw it as “un-American,” and a form of double taxation, although in fact much of the wealth derived from his investments had never been taxed under the existing system. A billion-dollar industry of lawyers, accountants, and insurance brokers, the so-called “wealth defense industry,” emerged to find and exploit the legal loopholes that have rendered the estate tax toothless.

For my dad, one of those steps was leaving New York for legal residence in Florida and the tax benefits it provided. But my mother, a professional dancer, missed Manhattan, and slowly began to push back, to the point where it almost blew their marriage apart.

Estate tax exemption is again up for renewal under Trump

In 2007, a few months after my first son was born, my father was diagnosed with terminal cancer. It was a year of great joy and pain. Now I had a new appreciation for his desire to leave financial security to his family. But since my dad’s passing in 2008, wealth inequality in the US has skyrocketed. For many Americans, the meritocracy that is at the heart of the American Dream, and that my dad benefited from, is becoming less and less achievable.

The estate tax exemption which was raised to more than $24 million for a couple in 2017 by the first Trump administration is now up for renewal. If this tax were fairly applied and enforced, it could help tens of millions of Americans struggling to meet the costs of education, housing, and health care, and help restore the social mobility that makes our country so unique.  

But beyond any one policy, the real question is: what is the inheritance we want to leave our children? For me, it goes beyond financial security to democracy itself. As Supreme Court Justice Louis Brandeis said, “We can have democracy in this country, or we can have great wealth concentrated in the hands of a few — but we can't have both.” A fair tax system is where that answer starts.

Justin Schein is a filmmaker. His documentary "Death & Taxes" is screening as part of the Milwaukee Film Festival on May 1 and 4.