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Milton Friedman's greatest regret.

The federal government discovered the perfect crime in 1943: make employers collect taxes before workers ever see their paychecks. You think you earn $60,000 per year, but you actually earn $75,000 and hand over $15,000 to politicians without… pic.twitter.com/mj9E9ARbNQ

— Handre (@Handre) June 6, 2026

Milton Friedman's greatest regret.

The federal government discovered the perfect crime in 1943: make employers collect taxes before workers ever see their paychecks. You think you earn $60,000 per year, but you actually earn $75,000 and hand over $15,000 to politicians without ever touching it. The psychological difference is enormous.

Before payroll withholding, Americans wrote quarterly checks directly to the Treasury. Picture yourself sitting at your kitchen table, writing a $3,750 check to the IRS every three months. The pain was immediate and visceral. Politicians faced constant pressure to justify every dollar because citizens felt the extraction in real time.

Withholding transforms this concrete loss into an abstract accounting entry. Your employer becomes an unpaid tax collector, and you never experience the actual cost of government. Worse, most people celebrate their tax refunds as government generosity rather than recognizing them as interest-free loans they provided to politicians. The Treasury collects your money throughout the year, spends it immediately, then returns your own cash and receives gratitude.

This system enables the explosion in government spending you witness today. Defense contractors billing $640 for toilet seats, agricultural subsidies for corn syrup, and congressional salaries for 535 people who rarely show up to work. When taxation feels painless, voters stop demanding accountability for how their money gets spent.

Milton Friedman helped design withholding as a wartime emergency measure and later called it his greatest regret. Free market economists recognized that the psychological pain of direct taxation creates political pressure for fiscal restraint. The temporary always becomes permanent in government hands, and the emergency justification disappears while the extraction mechanism remains forever.