Read the 5 Most Relevant Technically Speaking Columns of 2025

A year-end retrospective isn’t just an opportunity to revisit what was written over the last year. It’s a chance to look at what ideas endured, which still get cited back to us, and most importantly, which still echo because the underlying problems remain unaddressed.

In the spirit of self-audit and second opinions, here are some columns from the past year that have held up—not because they were trendy when written, but because they address issues that will still be with us in 2026.

Trump Tax Law Should Spur States to Split From Federal ‘Pendulum’. The 2025 tax-and-spending package should have prompted states to decide if it was in their best interest to keep their tax codes tethered to Washington’s ideological swings. No tax on tips, no tax on overtime, no tax on car loans, no tax on Social Security—and none of these being actual exemptions but instead capped deductions—makes it clear states should decouple more aggressively and embrace their own stable baselines. This one, which ran in July, is even more relevant today. Read More

Musk, Ramaswamy Can Target Inefficiency by Closing the Tax Gap. Since this column ran in early January, the Department of Government Efficiency has come and gone. Yet the tax gap stubbornly remains. The commission’s rhetoric on efficiency never translated into equitable tax policy action. That is perhaps unsurprising when auditing wealthy taxpayers—the most cost-effective fix—remains politically inconvenient. Read More

The Real Capital Gains Tax Loophole Isn’t Borrowing—It’s Dying. The real engine of capital gains avoidance isn’t leverage and borrowing, but death. The 2025 tax law did nothing to resolve this debate but instead preserved the step-up basis and left the largest capital gains expenditure intact. The loophole survives, and the revenue leak remains, as the politics of taxing unrealized gains proves insurmountable for another year. This column ran in April. Read More

IRS Shift to Immigration Enforcement Hurts Voluntary Tax System. Since this column ran in May, the broader immigration crackdown by the federal government has only accelerated—and with it, the quiet logic behind noncompliance. The idea that some immigrant workers may opt to roll the dice on not filing taxes rather than risk drawing attention to themselves has only gained strength. Shifting tax enforcement priorities from revenue collection to immigration politics erodes deterrence—and the foundation of a voluntary tax system. Read More

Supreme Court Will Define a ‘Just’ Tax Foreclosure Compensation. Sometimes a case reaches the US Supreme Court that feels like it should have been resolved when the justices were still posing for black-and-white daguerreotypes. Pung v. Isabella County is one of those cases—asking whether a “just compensation” for a tax foreclosure means fair market value or whatever the government gets at auction. It’s an issue that, remarkably, has survived more than a century of tax sales and constitutional law without being settled—we hope to get an answer in 2026. This column ran in October. Read More

Writing about tax and policy is partially an exercise in forecasting relevance. The pieces revisited here offered at least a partial weather report—we called for rain, and now we’re watching puddles form on the street. That these arguments still matter says less about the columns themselves and more about the persistence of the problems they tackled.

If experience is what corrects earlier logic, then let’s hope 2026 is a year full of attempts—so we have plenty to revise. Not breakthroughs necessarily, but enough serious engagement with these problems that next year’s retrospective can’t read the same with just some dates moved around.

Andrew Leahey is an assistant professor of law at Drexel Kline School of Law, where he teaches classes on tax, technology, and regulation. Follow him on Mastodon at @andrew@esq.social.

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