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Planet Money

Should the fine have to fit the crime?

with Ken Jopie, Michael O'Hare, Sam Gedge

Published October 24, 2025
View Show Notes

About This Episode

The episode follows Alaska bush pilot Ken Jopie, who lost his $95,000 Cessna after being convicted of felony bootlegging for flying a six-pack of beer into a dry village, and has spent over a decade fighting the forfeiture. Through Ken's case, law professor Michael O'Hare and attorney Sam Gedge explain the Eighth Amendment's Excessive Fines Clause, how a 1998 Supreme Court case (Bajikajian) established limits on economic punishments, and how lower courts have since applied that standard unevenly. The conversation explores why fines and forfeitures can be constitutionally excessive, the incentives that drive governments to rely on them, and why Ken's case could prompt the U.S. Supreme Court to clarify the law.

Topics Covered

Criminal justice reform Prison system Police work and detective work Lawsuits War on drugs Asset forfeiture Excessive fines clause Eighth Amendment Alcohol prohibition in Alaska Supreme Court cases

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Quick Takeaways

  • Alaska bush pilot Ken Jopie was forced to forfeit his $95,000 Cessna after a felony bootlegging conviction involving a six-pack of beer destined for a dry village, raising questions about proportionality in economic punishments.
  • The Eighth Amendment's Excessive Fines Clause, long overlooked, became a key tool against harsh forfeitures during the war on drugs, especially after the 1998 Supreme Court case involving Hosep Bajikajian.
  • In Bajikajian, the Supreme Court held that taking $300,000 for failing to file a cash-reporting form was unconstitutional, introducing the idea that fines cannot be "grossly disproportionate" to the offense.
  • Lower courts have interpreted "grossly disproportionate" very differently, with some scrutinizing fines case by case and others effectively rubber-stamping severe economic penalties.
  • A Washington State case where a man living in his truck was hit with a $500 towing fee shows how some courts consider an individual's circumstances when deciding if a fine is excessive.
  • Many courts are reluctant to aggressively enforce the Excessive Fines Clause due to workload concerns, deference to legislative deterrence schemes, and financial dependence on fines and forfeitures.
  • Economic punishments create different incentives than prison terms because they generate revenue for governments rather than costs, potentially encouraging overuse of fines and forfeitures.
  • Ken's case is being pushed toward the U.S. Supreme Court by attorney Sam Gedge as a vehicle to clarify how strictly the Excessive Fines Clause should limit modern forfeiture practices.

Podcast Notes

Introduction and Ken Jopie's life as an Alaska bush pilot

Ken's air taxi business in remote Alaska

Description of Ken Air and the remoteness of his routes[0:25]
• Ken ran a small air taxi service in Fairbanks, Alaska called Ken Air, flying to villages and mining camps that were only accessible by air.
• He used a Cessna Skywagon, a small single-propeller six-seat airplane, to transport people and supplies.

Ken's plane and typical cargo

Physical features and customization of the Cessna Skywagon[0:43]
• Ken's Cessna had blue and yellow stripes, his name painted on the tail, large cargo doors, and oversized tires for landing on rough terrain.
Unusual loads carried in the plane[1:26]
• Ken recalls hauling drums of gasoline, a partially disassembled ATV, and even a moose from a hunting trip.
• On one flight he transported seven or eight sled dogs loose in the back; they shed so much that he joked they seemed bald by the time they landed.

Ken Air goes out of business and foreshadowing of legal trouble

Closure of Ken Air and hint at the cause[1:40]
• The show notes that Ken has not flown his Cessna for some time and that Ken Air went out of business several years earlier.
• Listeners are told that the main reason ties back to an incident on a morning in April 2012.

The 2012 bootlegging incident involving Helen and the six-pack of beer

Ken's schedule and initial setup for the day

Jobs Ken had lined up on the April 2012 day[1:52]
• That day Ken planned to deliver a casket for a funeral and later haul parts and equipment for a mining operation.
• His first job was flying a regular customer, Helen, to the village of Beaver.

Loading Helen's supplies onto the plane

Helen's trip and cargo description[2:11]
• Helen and her sister arrived in a Suburban; Helen was visiting her husband in Beaver to celebrate her birthday.
• Ken helped load bags and boxes of supplies, including groceries and 12-packs of soda, into the plane and says nothing about the cargo seemed unusual.
Ken's approach to checking passenger luggage[2:31]
• Ken explains he was not in the habit of rifling through customers' belongings; he closed the cargo doors and prepared for takeoff.

Intervention by Alaska State Troopers and discovery of alcohol

Trooper stops the plane on the runway[2:55]
• As Ken was about to taxi onto the runway, an Alaska state trooper ran up and ordered him to shut down the engine and exit the plane.
Search of the plane and finding the beer[3:06]
• Officers searched the back of the plane, dumping Helen's belongings onto the tarmac.
• Among the groceries, Ken saw a six-pack of Budweiser in a clear plastic bag, which he immediately recognized as a problem.

Context: Beaver as a dry village and bootlegging laws

Alcohol ban in Beaver and similar Alaskan villages[3:36]
• Beaver is a small village along the Yukon River whose residents voted in 2004 to ban all alcohol, making it a dry town.
• Many Alaska towns have banned alcohol because of serious, ongoing problems with alcohol abuse.
Helen and Ken's legal exposure for bootlegging[3:45]
• State troopers ultimately found multiple cases of beer in Helen's luggage, and she faced bootlegging charges.
• Prosecutors also charged Ken with bootlegging, alleging he knowingly helped smuggle alcohol into a dry community.

Ken's prior incident and escalation to felony charges

Previous alcohol incident and change in stakes[4:11]
• Police had previously caught alcohol on Ken's plane once before in connection with a passenger, which resulted only in a misdemeanor.
• This time he was charged with felony bootlegging, a much more serious offense under Alaska law.

Trial, conviction, and sentencing in Ken's case

Jury assessment of Ken's knowledge of the beer[4:40]
• The jury accepted that Ken might not have known about all the hidden cases of beer but concluded he should have noticed the visible six-pack of Budweiser in a clear bag.
• Based on that, the jury returned a guilty verdict for felony bootlegging.
Judge's reaction and criminal sentence[4:54]
• Ken recalls glancing at the judge when the verdict was read and seeing that the judge appeared stunned by the jury's decision.
• The judge imposed the minimum sentence allowed: three days in jail and a $1,500 fine.

Mandatory forfeiture of Ken's plane

Alaska law requiring forfeiture of vehicles used in bootlegging[5:11]
• Under Alaska law, any plane involved in bootlegging becomes property of the state, leaving the judge no discretion.
• As a result, Ken was ordered to forfeit his Cessna Skywagon over the six-pack incident.
Scale of economic punishment and Ken's long fight[6:10]
• The forfeited Cessna was worth about $95,000, a massive loss compared with the three days in jail and $1,500 fine.
• Ken has spent roughly twelve years fighting to get the plane back, questioning how such a large forfeiture over a six-pack can be fair.

Framing the constitutional question about economic punishment

Hosts introduce the central inquiry of the episode

Scope of government power to impose economic penalties[6:10]
• The hosts position Ken's story within a broader question many U.S. courts are wrestling with: what are the limits on government power to take money or property as punishment for a crime?
• They ask what the Constitution says about economic punishments such as fines and forfeitures, and whether the fine has to fit the crime.

Ken's case and the Eighth Amendment's Excessive Fines Clause

Ken's lawyers link his plane forfeiture to a constitutional argument

Use of a short, somewhat mysterious phrase in the Constitution[7:58]
• Ken's lawyers base their challenge on the Eighth Amendment, focusing on a couple of words that deal with fines.

Law professor Michael O'Hare explains the Eighth Amendment

Reading the full text of the Eighth Amendment[8:10]
• Michael, a crime and punishment scholar at Marquette University, reads the Eighth Amendment aloud, noting it is one of the shortest constitutional provisions.
• He highlights that it prohibits excessive bail, excessive fines, and cruel and unusual punishment.
Public awareness of different Eighth Amendment protections[8:48]
• Michael observes that most people recognize the "cruel and unusual punishment" language, joking that even his kids invoke it when complaining about phone restrictions.
• By contrast, he says very few people are familiar with the Excessive Fines Clause, despite it being explicit in the text.

Historical obscurity of the Excessive Fines Clause

How little attention the clause received in modern legal education[9:07]
• Michael recounts that when he attended law school in the 1990s, he does not recall the phrase "excessive fines" being mentioned at all.
Shift during the war on drugs[9:41]
• He explains that the war on drugs in the 1970s and 1980s changed things, as governments passed laws imposing harsher prison sentences and larger economic penalties.
• Alongside fines, legislatures expanded the use of forfeitures, where property could be confiscated for being related to a crime.

Rise of criminal forfeiture as a punitive and funding tool

Examples of property subject to forfeiture under drug laws[10:46]
• Michael notes that planes and boats used to move drugs, houses connected to drug trafficking, and cars used to transport even small amounts of drugs can all be seized.
• Ken's plane forfeiture is described as a criminal forfeiture under these kinds of laws.
Dual role of forfeitures: punishment and revenue[10:51]
• The stated goal of forfeiture laws was to make crime unprofitable by stripping offenders of assets.
• Forfeitures also became a funding source for the war on drugs, as seized assets could be converted into equipment or auction proceeds for law enforcement.
• He mentions an example where an entire yacht was seized after police found a joint on board.

Defense lawyers look for constitutional limits on forfeitures

Searching for the right constitutional theory[11:13]
• Michael says that at first, defense lawyers were unsure which part of the Constitution could be used to challenge asset forfeitures.
• After trying different theories, the Excessive Fines Clause turned out to be the most promising basis for pushback.

The Bajikajian case: defining constitutional limits on fines and forfeitures

Facts of the Bajikajian cash-reporting case

Cash-reporting rules and discovery at LAX[12:28]
• The law required travelers leaving the U.S. with more than $10,000 in cash to report it on a government form.
• Hosep Bajikajian and his family attempted to leave LAX with over $300,000 in cash without filing the form, and a cash-sniffing dog detected the money.
Government's attempted forfeiture of all the cash[12:10]
• Under federal law, failure to report meant they had to forfeit the full $300,000-plus to the U.S. government.

Bajikajian's explanation and lack of drug connection

Purpose of the money and fear of authorities[12:21]
• Bajikajian claimed the cash was for repaying a loan and demonstrated that it came from legitimate, non-drug-related sources.
• He said he did not file the report because he came from a country where disclosing large cash holdings could lead to shakedowns by authorities, so he did not trust officials.
• The host remarks that, in a sense, he did end up being shaken down by losing the money.

Constitutional argument in Bajikajian

Defense lawyers invoke the Excessive Fines Clause[13:37]
• His lawyers argued that seizing over $300,000 for failing to fill out a form was incompatible with the Excessive Fines Clause, which forbids excessive economic punishments.
• They framed it as obviously disproportionate: a massive forfeiture for a mere reporting violation.

Context of harsh prison sentences and Eighth Amendment challenges

Failed attempts to limit long prison terms as cruel and unusual[13:58]
• The hosts describe that, in the 1980s, people challenged extremely long mandatory prison sentences for minor drug offenses as cruel and unusual punishment.
• The Supreme Court largely rejected those challenges, accepting decades-long sentences for small-scale offenses and effectively signaling that there were few constitutional limits on prison length.
• This background made many observers doubt that the Court would be willing to set strict limits on economic punishments.

Supreme Court's landmark ruling in Bajikajian

Court sides with Bajikajian and recognizes a limit on fines[14:58]
• Contrary to expectations, the Supreme Court held that the forfeiture of Bajikajian's $300,000 was unconstitutional under the Excessive Fines Clause.
• The decision effectively declared that there is a constitutional cap on how severe fines and forfeitures may be: the fine has to fit the crime.

Ambiguity of the "grossly disproportionate" standard

Supreme Court's vague guidance to lower courts[16:30]
• Michael explains that the Court said fines may be somewhat disproportionate to the offense but cannot be "grossly disproportionate" to its gravity.
• However, the Court did not spell out a precise test for what counts as grossly disproportionate, leaving significant room for interpretation.
• The hosts note that this vagueness seemed intentional, giving lower courts a chance to develop their own balancing approaches in applying the clause.

Initial optimism versus lower court reality

Defense lawyers' hopes for a powerful new tool[16:40]
• After Bajikajian, defense attorneys were optimistic that the Excessive Fines Clause could be a strong constitutional tool against unfair fines and forfeitures.
Lower courts' limited embrace of the clause[17:07]
• Michael says this optimism quickly met resistance in lower courts, which often were not very receptive to robust applications of the Excessive Fines Clause.

Modern practice: persistent severe fines and Ken's setback in Alaska

Continuing prevalence of heavy fines and forfeitures

Persistence of extreme-sounding economic penalties[19:17]
• Nearly three decades after Bajikajian, the hosts note that governments still impose many large fines and forfeitures, like taking Ken's $95,000 airplane over a six-pack of beer.

Alaska Supreme Court rejects Ken's Excessive Fines argument

Ken's appeal and outcome in the state's highest court[19:34]
• For about ten years, Ken's lawyers argued that forfeiting his plane was an unconstitutionally excessive fine.
• When the case reached the Alaska Supreme Court, the justices held that the punishment was not excessive under their interpretation.

Attorney Sam Gedge and efforts to bring Ken's case to the U.S. Supreme Court

Sam's focus on Excessive Fines cases

Monitoring new Excessive Fines decisions[20:02]
• Sam explains that through Westlaw he receives daily alerts for any new cases mentioning "excessive fines," reflecting his specialization.
• He says he is deeply enthusiastic about the Excessive Fines Clause and litigates many such cases.

Institute for Justice and prior Supreme Court victory

Organization's mission and incorporation of the clause[20:08]
• Sam works at the Institute for Justice, a nonprofit law firm that focuses on issues like private property and free speech.
• He notes that he and colleagues previously won a Supreme Court case holding that the Excessive Fines Clause applies not only to the federal government but also to state and local governments.

Judicial reluctance to enforce the Excessive Fines Clause

Courts treating the clause as a rubber stamp[21:07]
• Sam says that many judges are not enthusiastic about the Excessive Fines Clause and often fail to closely scrutinize fines and forfeitures.
• He characterizes many lower courts' approach as essentially a rubber stamp in favor of the government, rather than rigorous application of the constitutional protection.

Sam's reaction to the Alaska Supreme Court ruling and decision to appeal

Why Ken's case stood out to Sam[21:19]
• Reading the Alaska Supreme Court opinion, Sam saw it as one of the most extreme examples of a court not taking the Excessive Fines Clause seriously.
Moving to seek U.S. Supreme Court review[21:38]
• Sam contacted Ken, flew out to meet him, and proposed appealing to the U.S. Supreme Court.
• At the time of the episode, the U.S. Supreme Court is considering whether to take up Ken's case.

Two competing approaches to applying the Excessive Fines Clause

Robust, case-specific proportionality analysis

Questions asked by courts that take the clause seriously[21:28]
• Sam explains that some courts ask how serious the specific crime was and whether taking a particular asset, like a car, home, or plane, makes sense in that individual case.
• These courts engage with details such as the offender's role, the gravity of the offense, and the size of the penalty.

Example from Seattle: a man living in his truck

Facts of the Seattle towing and fine case[22:23]
• In Seattle, a man who lived in his truck overstayed in a city parking lot, leading the city to tow his vehicle and charge a $500 towing fee.
• The case reached Washington State's highest court, which examined whether this penalty was excessive for that specific individual.
Court's reasoning in finding the fine excessive[21:45]
• The court concluded that, for this man, the $500 fee was unconstitutionally excessive because he had no home, could not afford the amount, and the truck was both his shelter and transport to work.
• The decision illustrates a court considering both the nature of the violation (a parking issue) and the defendant's economic situation.

Need for individualized assessment of crime and person

Factors such courts weigh in drug and other cases[23:21]
• Sam suggests courts should consider whether a defendant is akin to a major trafficker like Pablo Escobar or more like a low-level addict when assessing proportionality.
• He emphasizes comparing the severity of the offense and the magnitude of the fine in the context of the particular person before the court.

Minimalist approach: zooming out and deferring to labels of seriousness

Courts that ignore case-specific details[23:37]
• Other courts, Sam says, merely note that a statutory offense is labeled a serious crime and treat that as sufficient to uphold large fines or forfeitures.
• These courts do not examine the individual facts closely, which results in very few findings that a fine is unconstitutionally excessive.

Michael O'Hare's study of how lower courts apply the clause

Empirical look at state and federal decisions[23:53]
• Michael reviewed hundreds of state and federal cases to see how courts have been interpreting and implementing the Excessive Fines Clause.
General pattern of lower court resistance[24:00]
• He concludes that most lower courts have declined to embrace a robust Excessive Fines Clause, generally avoiding strong enforcement.

Why many courts are reluctant to aggressively police excessive fines

Practical workload and floodgates concerns

Complexity of fact-specific proportionality review[24:23]
• Michael notes that truly applying the Excessive Fines Clause would require courts to dig into the specific details of each defendant's crime, finances, and life circumstances.
• Such intensive review could make cases longer and more resource-intensive.
Potential increase in appeals and constitutional challenges[24:33]
• He points out that if every parking ticket or fine became a potential constitutional issue, courts would face many more appeals.

Deference to legislative deterrence schemes and Alaska's bootlegging law

Alaska Supreme Court's reasoning in upholding Ken's forfeiture[24:48]
• The Alaska Supreme Court acknowledged that taking Ken's plane may sound extreme but emphasized the state's long and troubled history with alcohol abuse.
• The court viewed the harsh bootlegging statute as a deliberate response to serious problems in villages that chose to ban alcohol.
Mandatory penalties as deliberate deterrents[25:27]
• Michael explains that such laws are designed to be severe on purpose: if you bring any amount of alcohol into a dry village, you automatically lose your plane.
• Because the penalty is mandatory, there is no room for individualized pleas or mitigating arguments, which is supposed to deter people from offending.

Economic dependence of justice systems on fines and forfeitures

Fines and seized assets as funding sources[26:07]
• Over the past two decades, many police departments, prisons, and even courts have come to depend on revenue from fines and forfeiture auctions.
• Money from fines and confiscated cars, planes, and houses has become part of the financial model of criminal justice in many jurisdictions.
Risk that strong enforcement of the clause could disrupt this model[26:35]
• Michael suggests that if judges began robustly enforcing the Excessive Fines Clause, they could undermine this funding model, which may make courts wary.

Distorted incentives of economic punishment and the stakes of Ken's case

How fines and forfeitures create different incentives than prison terms

Costs versus revenues to the state[26:53]
• The hosts highlight a key difference: imprisoning people costs the government money, while fines and forfeitures bring in revenue.
• This structure gives governments a financial incentive to enact and enforce more economic penalties.

Ken's case as an opportunity to reset the rules

What Ken and his lawyers want from the Supreme Court[27:07]
• Ken and his legal team want the U.S. Supreme Court to establish clearer, stronger rules that limit excessive fines and push back against revenue-driven enforcement.
• They hope the Court will address how far governments can go in taking property like planes in response to relatively minor offenses.
Uncertainty about whether the Supreme Court will weigh in[27:19]
• At the time of the episode, the Supreme Court has not yet decided whether to hear Ken's case, and his lawyers are waiting to see if the Justices will engage with this debate.

Credits and closing

Production credits for the episode

Producers, editor, fact-checker, engineer, and executive producer[28:05]
• The episode was produced by James Sneed and Sam Yellowhorse Kessler with help from Luis Gallo, edited by Jess Strang, fact-checked by Sierra Juarez, and engineered by Ko Takasugi-Czernowin with help from Robert Rodriguez.
• The executive producer is Alex Goldmark, and the hosts for the episode are Jeff Guo and Sarah Gonzalez.

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Proportionality in punishment matters: when economic penalties like fines and forfeitures vastly exceed the gravity of an offense, they can undermine fairness and trust in the legal system.

Reflection Questions:

  • • Where in your own life or work might consequences be significantly out of proportion to the mistakes people make?
  • • How would your decision-making change if you explicitly asked whether each penalty or policy you support truly fits the underlying behavior?
  • • What is one rule or consequence you control that you could review this week to better align the severity of the outcome with the seriousness of the action?
2

Vague standards like "grossly disproportionate" invite a wide range of interpretations, so the way decision-makers choose to apply them becomes as important as the written rule itself.

Reflection Questions:

  • • What key standards or guidelines in your environment are phrased in vague terms that could be interpreted very differently by different people?
  • • How could you clarify your own criteria for fairness or proportionality so others know how you will apply them in practice?
  • • When you next face an ambiguous rule, what specific questions can you ask to ensure you are applying it consistently and transparently?
3

Economic incentives can distort judgment; when an institution financially benefits from imposing penalties, there is a risk that revenue, not justice, will quietly drive its behavior.

Reflection Questions:

  • • In what areas of your organization or community do financial incentives risk pulling decisions away from the values you claim to uphold?
  • • How might you redesign one incentive or metric so that it rewards fair outcomes rather than simply generating more revenue or activity?
  • • What is one current process where you should ask, "Who benefits financially from this decision, and does that align with our stated goals?"
4

Individual circumstances matter: the same monetary penalty can be trivial for one person and devastating for another, so fairness often requires looking beyond one-size-fits-all rules.

Reflection Questions:

  • • Where are you currently applying uniform standards or penalties without considering how they land on different people?
  • • How could you build simple checkpoints into your decisions so you pause to consider context-like someone's resources, history, or alternatives-before finalizing a consequence?
  • • What is one domain in your life (parenting, management, community roles) where you could pilot more individualized responses without sacrificing clarity or consistency?
5

Deterrence and justice must be balanced; making punishments extremely harsh to scare people away from misconduct can backfire if the penalties seem arbitrary or unjust.

Reflection Questions:

  • • Where are you or your organization relying heavily on fear of punishment as the main tool to shape behavior?
  • • How could you complement or replace deterrence-based strategies with approaches that build understanding, buy-in, or alternative options?
  • • What is one policy you support that you should revisit to ensure it not only deters harmful actions but also maintains a sense of proportional fairness?

Episode Summary - Notes by Taylor

Should the fine have to fit the crime?
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