Land of the Free (For Me, But Not for Thee)

By Shane Shipman — December 8, 2025

We often speak of America as “the land of the free.” But freedom appears conditional — especially depending on your wallet, your past, and how the law chooses to see you.

There are real cases that show how the criminal justice system can impose severe punishments for minor, nonviolent offenses. In 1983, Alvin Kennard took roughly $50.75 from a bakery and, under an old habitual-offender law, ended up serving decades in prison before a judge resentenced him to time served. (Washington Post — Alvin Kennard)

Other cases are no less stark. The U.S. Supreme Court in Rummel v. Estelle upheld a life sentence with the possibility of parole under a three-strikes style law for repeated nonviolent offenses involving relatively small dollar amounts — a reminder that draconian sentencing has deep legal precedents. (Rummel v. Estelle — decision (Justia))

In Texas, Tyrone Brown was once sentenced to life imprisonment for nonviolent parole violations tied to a very small offense; after public pressure and review he was eventually released/pardoned. (The Guardian — Tyrone Brown, ABC News)

We repeat “land of the free,” yet freedom apparently comes with a price tag. If you’re poor and desperate enough to steal $12 worth of bologna, we lock you in a cage. If you’re rich and cunning enough to steal millions through creative accounting, we send a strongly worded letter and let you keep the yacht.

The justice system has repeatedly shown it will mete out very harsh punishments for minor acts, especially under habitual-offender laws. Where I make a factual claim, I cite sources above and list them below so readers can check for themselves.

This is not justice. It’s a two-tiered system:

• Shoplifting diapers because your baby needs them? Felony — and potentially years behind bars under habitual-offender statutes.
• Defrauding thousands of retirees through predatory financial products? Civil settlements, fines, and often no criminal charges — and stocks can rebound after the settlement news.

Poverty is treated like a moral failing that deserves incarceration, while white-collar crime is treated like a business expense that deserves a tax write-off. Until corporate leaders face criminal consequences proportionate to the damage they cause, until punishment reflects the scale of harm, we should stop pretending the law is blind.

Call it what it is: freedom for the powerful, incarceration for the desperate. The rest of us get the land of “three strikes and a sandwich.”

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Sources & further reading

• Washington Post — "Alvin Kennard freed after serving 35 years for $50 theft" (Aug 29, 2019)
• ABC News — "Man who spent 36 years in prison for stealing $50 from a bakery" (Aug 29, 2019)
• Justia — Rummel v. Estelle (445 U.S. 263) — Supreme Court decision (1980)
• Background: Rummel v. Estelle (Wikipedia)
• The Guardian — "Two dollars bought mugger 17 years in jail" (Mar 19, 2007) — Tyrone Brown coverage
• ABC News — "Update: Man Jailed for Joint Set Free" (Tyrone Brown follow-up)
• U.S. DOJ — "Wells Fargo Agrees to Pay $3 Billion..." (Feb 21, 2020)
• Washington Post — "Wells Fargo reaches $3 billion settlement" (Feb 21, 2020)

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Tags: criminal justice, three-strikes, habitual offender, white-collar crime, corporate accountability, Alvin Kennard, Wells Fargo