{"id":261,"date":"2026-05-26T15:38:50","date_gmt":"2026-05-26T15:38:50","guid":{"rendered":"https:\/\/movingandmortgagehub.com\/?p=261"},"modified":"2026-05-26T15:38:50","modified_gmt":"2026-05-26T15:38:50","slug":"tax-me-if-you-can","status":"publish","type":"post","link":"https:\/\/movingandmortgagehub.com\/?p=261","title":{"rendered":"Tax Me If You Can"},"content":{"rendered":"<article>\n<div><ul><li><span>Share on Facebook<\/span><\/li>\n<li><span>Share on Twitter<\/span><\/li><li><i><?xml version=\"1.0\" encoding=\"UTF-8\"?>\n<svg>\n<\/svg><\/i><span>Share on Bluesky<\/span><\/li><li><span>Email<\/span><\/li><li><span>Comments<\/span><\/li><\/ul><\/div>\n<div>\n<p><span>Democracy, for most<\/span> of its existence, has managed to coexist with oligarchy, but only on the condition that oligarchs exert their influence quietly. Citizens, including ordinary Americans, are generally willing to tolerate the super-rich, but the arrangement breaks down when a small group of exceedingly wealthy people are perceived to be distorting and impairing democracy for their own gain, disrupting the fragile illusion that they are not, in fact, running the show.<\/p><p>Read more <a href=\"https:\/\/movingandmortgagehub.com\/?p=259\">The Pentagon Could Name Thousands of Unknown Soldiers. Families Want to Know Why It Hasn\u2019t.<\/a><\/p>\n<p>America\u2019s oligarchs, at least historically, have kept their end of the bargain. But their accelerating wealth share and absence of serious political setbacks in recent decades have spawned a growing sense of entitlement and omnipotence\u2014indeed, untouchability. When I started teaching a seminar on oligarchs at Northwestern University in 2007, students could barely conceive of the notion of oligarchy in America\u2014only one hand went up when I asked whether they thought we had oligarchs or oligarchy here. By 2016, their worldview had already flipped: Only one hand went up when I asked how many students would describe our political system as a <em>democracy<\/em>.<\/p>\n<p>In the interim, the Supreme Court\u2019s rulings in <em>Citizens United<\/em> <em>v. FEC<\/em> and other campaign finance cases unleashed a gusher of political spending by the richest Americans and their businesses, with each cycle setting new records. So much of it was legally untraceable that a fresh term, \u201cdark money,\u201d entered the lexicon. In 2012, for the first time, a major presidential candidate was bankrolled almost exclusively by a single oligarch: The late casino billionaire Sheldon Adelson kept Newt Gingrich\u2019s foundering Republican primary campaign alive with a $20 million infusion of super-PAC funds. <em>Slate<\/em> called it \u201camong the largest known political donations in US history.\u201d By November 2024, it didn\u2019t even rank in the top 25.<\/p>\n<p>The biggest spender during the 2024 cycle, according to OpenSecrets, was Elon Musk at more than $291 million. Former Treasury Secretary Andrew Mellon\u2019s grandson Timothy, a man few Americans knew existed, spent about $197 million, and Adelson\u2019s widow, Miriam, ranked third with more than $148 million. All told, 100 individuals invested $2.4 billion in the 2024 election\u2014almost half the total cost of the presidential contest and 16 percent of all federal election spending. The problem is bipartisan\u2014oligarchs poured money in for Democrats and Republicans alike.<\/p>\n<p>How did America\u2019s oligarchs grow so willing to openly rub their wealth power in our faces? Well, a big part of it has to do with their success in neutering perhaps the greatest threat to their dominance: the ability of the government to tax them and to hold those who cheat accountable.<\/p>\n<p><span>Nothing embodies<\/span><span> this<\/span> atmosphere of oligarchic untouchability quite like the OffshoreAlert conferences that investigative journalist David Marchant has been running for the last quarter-century. As Jack Blum, a veteran tax compliance lawyer and investigator who has sat on Marchant\u2019s panels over the years, described it to then\u2013<em>Wall Street Journal<\/em> reporter Jesse Drucker, the annual conferences remind him of \u201cthat famous bar in <em>Star Wars<\/em> where they all come together\u2014the good guys, the bad guys, the seriously guilty\u2014and they all exchange information on neutral territory.\u201d<\/p>\n<p>On stage and in the audience are IRS special agents, representatives from the Department of Justice, officials from the Securities and Exchange Commission, and CIA and FBI agents; white-collar defense lawyers and accountants from the Wealth Defense Industry; investigative reporters; private detectives for ex-spouses and business partners trying to recover offshore assets; cryptocurrency players; whistleblowers; bankruptcy attorneys; judges and prosecutors; and officials from Caribbean tax havens. A few oligarchs show up, too, and the occasional academic like me. The networking that happens at the well-attended cocktail parties is as important as the formal sessions.<\/p>\n<p>The gatherings carry a whiff of risk. At one event, Marchant announced that a speaker from the previous year had been shot in the head in the Bahamas during an assets dispute. And \u201cover the years,\u201d Drucker wrote, \u201cat least two speakers at Mr. Marchant\u2019s conference have been served with subpoenas on the dais.\u201d<\/p>\n<p>Marchant, despite a formidable demeanor, has had to watch his own back after daring to expose the workings of offshore secrecy jurisdictions and the people who use them. \u201cI knew the investigative journalism side was risky,\u201d he told me when we sat down for an interview at his 2023 conference at Miami\u2019s Ritz-Carlton. \u201cI got threatened by Russians more than once.\u201d He sometimes got so spooked that he would go sleep at a friend\u2019s house. \u201cIt was affecting me mentally,\u201d he admitted. \u201cI would put my key in the ignition, and somewhere in the back of my mind, I was expecting the car to blow up.\u201d<\/p>\n<p>He\u2019s no ideological crusader, so why subject himself to these dangers? \u201cFraud pisses me off,\u201d Marchant explained. \u201cThe day that it stops pissing me off, I\u2019ll do something else.\u201d His investigations have been responsible for the criminal indictments of more than a dozen people, half of whom went to prison: \u201cIt\u2019s very satisfying.\u201d<\/p>\n<p>His conferences are unique in that they offer a glimpse of the strangely direct interface between the Wealth Defense Industry and the civil servants working to enforce laws on tax evasion and money laundering. And hanging over those enforcers, almost like a shadow attendee, is the saga of their forebear Dick Jaffe, a renowned former special agent who worked in the IRS\u2019s intelligence division half a century ago. It was Jaffe\u2019s travails that would set the tone for today\u2019s toothless IRS and help to explain how America\u2019s oligarchs became so emboldened.<\/p>\n<p>Tax fraud in the Caribbean was rampant even back then, obvious to anyone who bothered to look\u2014and Jaffe was looking. In 1973, he and one of his informants were investigating money laundering by organized crime figures\u2014part of an IRS effort dubbed Operation Tradewinds\u2014when they got hold of a client list for an American-owned, Bahamas-based entity called Castle Bank. The list, when cross-referenced with other materials Jaffe\u2019s team obtained, amounted to a smoking gun implicating a who\u2019s who of rich and powerful Americans who were hiding money from the taxman.<\/p>\n<p>Initially, Jaffe was celebrated within the IRS for his coup and given additional resources to build individual cases. But that was before the oligarchs he\u2019d exposed began calling in favors. President Richard Nixon promptly installed Donald Alexander\u2014a tax attorney who represented ultrawealthy clients and was openly hostile to enforcement\u2014as his new IRS commissioner. Alexander proceeded to dismantle all Jaffe had accomplished, crush the Castle Bank investigation, and even target the agents who took part in it. It was an epic, in-your-face flex of oligarchic wealth power. \u201cHe was quite willing to talk about his experience and somewhat bitter about what had happened to him,\u201d recalled Blum, who sat down with Jaffe to compare notes on offshore tax evasion not long after Jaffe was driven from the IRS.<\/p>\n<p>Blum had pursued a parallel career as an attorney for Senate committees investigating white-collar crimes and international tax evasion. Later, in the private sector, he advised IRS auditors and special agents and helped create nonprofits that work to combat tax fraud and secrecy in financial transactions. The way the IRS threw Jaffe under the bus, Blum told me, did not go unnoticed by his colleagues. \u201cWhat that story did,\u201d he said, \u201cwas make it impossible for IRS to deal with the problem of tax evasion by the rich for a full 20 years, if not longer.\u201d<\/p>\n<p>Blum experienced this fallout firsthand. During the 1990s, a bank client in the Cayman Islands provided him with reams of information about the activities of 20 very rich Americans who were cheating the IRS out of millions every year. The informant urged Blum to deliver the materials to the IRS in Miami, which he did. By coincidence, the special agent he met with had worked with Jaffe almost two decades earlier. \u201cHe looked at all the documents and information I had and said to me, \u2018Get out of here!\u2019\u201d<\/p>\n<p>Blum wasn\u2019t sure he\u2019d heard right. He\u2019d expected excitement, maybe gratitude. Special agents were supposed to be working major criminal cases exactly like this one. He asked the guy what the problem was. \u201cThis whole thing is a career killer,\u201d the agent said.<\/p>\n<p>Blum left the meeting dazed. \u201cI came in with evidence, and it should have been a slam dunk, and here I\u2019m being told to get lost,\u201d he said.<\/p>\n<p>This snubbing, ironically enough, took place during what former longtime IRS special agent Ralph Gay described to me as the criminal investigation division\u2019s \u201cfinancial heyday.\u201d Gay, whom the IRS hired only months before Jaffe\u2019s Castle Bank breakthrough, would run into similar resistance from higher-ups. The Department of Justice, for instance, \u201ckept throwing roadblocks up\u201d after a Colombian money-laundering investigation he was running implicated a politically connected American bank owner\u2014the banker was never indicted. In the mid-1990s, Gay, who\u2019d been promoted to run the IRS\u2019s finance division, was able to secure ample funding from Congress for CID, but only because its investigators were now focused on narcotics and foreign money laundering\u2014not US oligarchs defrauding the treasury. Whenever the super-rich felt threatened, he recalled, \u201cwe were reined in.\u201d<\/p>\n<p>The IRS says its criminal investigations unit today has \u201cabout 2,100\u201d armed special agents, which is less than two-thirds the 1996 peak and roughly the same number as it had during the 1970s. In other words, the federal government is devoting about the same amount of resources to investigating major tax crimes, money laundering, and bank secrecy that it did a half-century ago, even though the number of taxpayers is vastly larger, the ranks of the ultra-rich more bloated, and the Wealth Defense Industry at full maturity.<\/p>\n<p>There has been pushback from time to time against the forces of oligarchy. In 2022, under President Joe Biden, Congress approved an $80 billion increase in IRS funding over a decade, with more than half of it slated to restore the agency\u2019s ability to go after the super-rich. This victory was short lived. By March 2025, Republicans had slashed that $45.6 billion enforcement budget to just under $4 billion\u2014a 91 percent decrease. A month later, the agency was ordered to abandon rules requiring that certain lucrative tax shelters be reported, making the work of overwhelmed auditors vastly harder.\u00a0The result: another $100 billion that America\u2019s wealthy would never pay.<\/p>\n<p>On Biden\u2019s watch, the IRS had also set up a unit to audit complex partnerships that the Wealth Defense Industry uses to obscure its clients\u2019 tax obligations. In September 2025, Jesse Drucker, now at the <em>New York Times<\/em>, reported that \u201cnearly the entire senior team of IRS lawyers with partnership expertise has left the agency, an unusual mass exodus even for a new administration.\u201d<\/p>\n<p>By early 2026, the IRS was a  than at any time in over a century.<\/p>\n<p>The lack of political will to meaningfully pursue rich tax evaders has created, within oligarchic circles, something akin to a highway that has posted speed limits, but where the people with the hyper-luxury cars know there are no police, speed traps, or cameras. The most daring and reckless are free to drive as fast as they like with impunity. Or, as Blum more colorfully cast the government\u2019s self-imposed ineptitude: \u201cIt\u2019s not good enough to have a bicycle chasing a Ferrari. You\u2019ve got to deflate the bicycle\u2019s tires to cripple it.\u201d<\/p>\n<p><span>The IRS publishes<\/span> data each year on the tax gap, the difference between the estimated amount due and what it collects. This is noncompliance, and the numbers are staggering. The agency estimated that the gap for 2022, the most recent year available, was $696 billion\u2014roughly the combined 2024 budgets for the departments of Agriculture, Education, Homeland Security, State, and Treasury. But that\u2019s a gross underestimate, because in the realm of offshore tax havens, the IRS is flying blind. \u201cThe projections do not fully represent noncompliance,\u201d the IRS report gingerly admits, \u201cbecause data are lacking.\u201d Charles P. Rettig, the IRS commissioner in 2021, put the gap at about $1 trillion per year, significantly greater than America\u2019s bloated defense budget. For perspective, the 1975 tax gap was only $40 billion. In short, even as the ability of the government to collect taxes owed has declined enormously, the ability of certain Americans to evade them has exploded.<\/p>\n<p>Noncompliance is not an option for most people. Not only do our employers report our earnings to the IRS, but they also withhold taxes from our paychecks and forward the money to Washington. Only 1 percent of wage earners misreport their income, because they <em>will<\/em> be caught. Audits of ordinary workers are entirely computerized, meaning \u201cthere\u2019s a limited ability for you <em>not<\/em> to do the right thing when you have a W-2,\u201d a retired special agent told me. The vast majority of US taxpayers \u201cdon\u2019t have an opportunity to cheat.\u201d<\/p>\n<p>The lion\u2019s share of the tax gap is caused by Americans who make money from money. There is no third-party reporting, so they can structure and hide their income as they wish. IRS data show that the misreporting and noncompliance rate for people in this category shoots up to 55 percent. The agency estimates that three-quarters of the tax gap is due not to corporations, but to individuals gaming the system. <\/p>\n<p>In this tug of war between the oligarchs and the tax collectors, the latter are disadvantaged in almost every conceivable way. The Wealth Defense Industry has endless time and money to serve its clients, but the civil servants working to keep those clients honest have vanishingly little of either. Congress imposes a three-year statute of limitations on tax enforcement, which kneecaps the ability of the IRS to complete complicated audits and investigations. Agents don\u2019t want to tackle those cases \u201cbecause they won\u2019t be fast, they are difficult, and it takes a lot of time and energy,\u201d a former IRS executive told me. \u201cAnd frankly, after a year-and-a-half of working a case, the agent gets tired of it, and they\u2019re like, oh, I just want this to be over with.\u201d<\/p>\n<p>The extraordinary complexity of tax returns for the super-rich makes auditors reluctant to dig deeply. A successful auditor \u201chas to be somebody that\u2019s aggressive,\u201d the former executive noted, but aggressive auditors and special agents aren\u2019t the norm nowadays. \u201cSometimes, I feel like they just want to hit their metrics and targets. How quickly can I deal with this so I can move on to the next one and make my boss happy?\u201d she said. \u201cSo, do they tackle those high-wealth people very often? Probably not.\u201d<\/p>\n<p>Willingness is only the first obstacle. Because when an intrepid IRS auditor is inspired to wade through boxes and boxes of records, and detects substantial tax problems, the oligarchy class has near-endless resources to fight back. Billionaires can afford to hire the nation\u2019s most high-powered tax attorneys and, if targeted, unleash them upon the IRS. Their strategy is to barrage the enemy with issues and objections so as to run out the clock. \u201cThose people have the capacity to drag on these investigations, civilly or criminally,\u201d a retired special agent with long experience observed, and \u201ceventually they go into settlements, and they may be paying less simply because it\u2019s settling.\u201d<\/p>\n<p>The oligarchs are represented by major law firms that bring in legions of former IRS agents and federal prosecutors to assist in the defense. \u201cThere\u2019s a revolving door,\u201d Blum confirmed. \u201cThat\u2019s where the money is.\u201d Indeed, nearly all of the former IRS special agents and prosecutors I interviewed for my book joined private tax defense practices after leaving the agency. Doesn\u2019t that feel like going over to the dark side, I asked one of them. \u201cNo, no, no, no,\u201d he exclaimed. \u201cEverybody realizes that\u2019s what basically happens.\u201d Jeffrey Marcus, a former federal prosecutor who switched sides, drew a laugh at the 2017 <em>OffshoreAlert<\/em> conference when he joked, \u201cas a defense lawyer, I just want to note that one man\u2019s crook is another man\u2019s client.\u201d<\/p>\n<p>The targeted oligarch\u2019s defense team presents the IRS and Justice Department with the certainty of an exhausting battle, whereupon a delicate dance ensues\u2014each side probing the other\u2019s strengths and weaknesses\u2014to reach a settlement everybody can live with. There are two sides to the tax practices of big accounting and law firms. The first, blandly called \u201ctax planning,\u201d is to create complex and often opaque legal structures to minimize what clients can get away with paying. The other side, \u201ctax controversy,\u201d kicks in when extravagant tax planning lands a client in legal trouble. <\/p>\n<p>A veteran East Coast defense attorney who represents wealthy clients in tax disputes explained to me how it works. First, she and the government lawyers tussle over dozens, sometimes hundreds, of questions and technicalities. When the IRS is worn down, tensions are rising, and it looks like the dispute might end up before a judge, she will say something like, \u201cI think you\u2019ve got litigating hazards and I\u2019ve got litigating hazards. I think it\u2019s 50-50. Let\u2019s split the baby.\u201d<\/p>\n<p>The mind-numbing arcana of the tax code\u2014to which the Wealth Defense Industry has contributed over the years\u2014helps speed the process along. \u201cThe tax laws are sufficiently complicated and sufficiently screwed up so that there\u2019s plenty of wiggle room,\u201d Blum explained. If the sides can agree on a split, the oligarch\u2019s unpaid taxes just got cut in half. The auditors are happy because they collected some revenue\u2014a career success. The bosses are pleased because they\u2019ve put a tiny dent in the tax gap. And the oligarch, who often comes out ahead thanks to the investment gains on all those deferred taxes, can write a check and forget it ever happened. \u201cIf you settle, there is never any record or revelation that there has been a tax issue,\u201d the defense attorney explains. \u201cIt\u2019s completely private.\u201d<\/p>\n<p>The odds of a 0.0001 percenter ever having to write that check were always low, and they have dropped even lower as Congress has slashed the IRS\u2019s resources over the decades. \u201cIt\u2019s audit roulette,\u201d said one retired special agent. For most of his career, this agent told me, super high-income individuals were audited at an annual rate of about 2 percent. During the last decade, the rate dropped to well below 1 percent. Which means the audit roulette revolver has more than 100 chambers, and the unlucky one doesn\u2019t even contain a deadly bullet\u2014it\u2019s more like a peashooter.<\/p>\n<p>The rare cases that aren\u2019t settled end up in a specialized venue, Tax Court, where they are overseen by a judge trained in the byzantine world of the federal tax code. The goal of these civil proceedings is to determine the meaning of given sections of the code and whether taxes and penalties are owed. The battles are highly technical, the evidence and arguments arcane, and every word of every ruling gets larded into the appendices of the tax code, further deepening the complexity problem for the enforcers while opening up new avenues for the cheats.<\/p><p>Read more <a href=\"https:\/\/movingandmortgagehub.com\/?p=257\">These Photos Reveal Strange Sea Creatures Scientists Have Never Seen Before<\/a><\/p>\n<p>The biggest winner is the US Wealth Defense Industry, which rakes in tens of billions of dollars in fees every year to protect\u2014and expand\u2014the fortunes of its upper-crust clients. On the very rare occasions when an oligarch ends up in criminal court, their savvy lawyers and accountants can mystify their audience into submission. Criminal tax cases are not overseen by specialized judges, and unless a guilty plea is negotiated, a jury of 12 ordinary citizens is tasked with passing judgment based on a legal narrative so convoluted that even assistant US attorneys and expert witnesses struggle to understand the intricacies. \u201cWe teach our agents to treat a jury\u2014and I know this sounds terrible\u2014but you treat a jury like eighth graders,\u201d a former IRS special agent told me. \u201cI\u2019ve heard that lately they\u2019ve actually lowered it to sixth grade.\u201d<\/p>\n<p>Prosecutors also have to get past the public\u2019s dislike of the IRS. Seat a juror who resents the taxman, and they \u201cmay pull the trigger for the taxpayer and vote for acquittal,\u201d said a different former special agent. The combination of public mistrust and technical complexity gives the Wealth Defense Industry a near-impenetrable shield for their richest clients.<\/p>\n<p>\u201cThe American criminal justice system is a British antique from the 16th century,\u201d Blum told me. It works beautifully, he said, for the theft of a cow off the village commons: \u201cEverybody in the village knows what a cow is, and everybody in the village has a pretty good idea whose cow it is\u2014probably by name.\u201d But a criminal tax case might involve \u201ca Scottish limited partnership, a trust in an offshore jurisdiction, a moving trust\u2014I can go on and on about the devices, foundations, all sorts of things to conceal ownership and hide the way things move,\u201d Blum said. \u201cYou\u2019ve got to prove this stuff to a group of people who have never heard of half of it.\u201d<\/p>\n<p>Meanwhile, \u201cyou\u2019ve got a paper trail that is a bloody nightmare and the typical prosecutor looks at that and says, \u2018Dear God, what am I going to do with all this paper? And the jury, before we go very far, is going to hate me.\u2019\u201d<\/p>\n<p><span>The government\u2019s unwillingness<\/span> to hold oligarchs to account matters, and not just because a few rich guys get off scot-free. Our current predicament\u2014laws are ignored and allegations of high-level corruption are becoming the norm\u2014is intimately connected to a series of prominent victories by the rich against the government, showing others it\u2019s possible to beat the system, and here\u2019s how it\u2019s done. This has eliminated the single most important weapon in any law enforcer\u2019s arsenal: deterrence. Because, as one former special agent put it, with tax evasion, \u201cyou\u2019re not going to prosecute your way out.\u201d <\/p>\n<p>The array of \u201caggressive\u201d but technically legal tax avoidance schemes available to America\u2019s super-rich is so extensive that it\u2019s baffling anyone would resort to outright tax evasion, which is illegal. That is, until you consider how easy it has become for them to get away with it. If investigators identify 30,000 people committing tax evasion, \u201cyou can\u2019t do 30,000 cases and put 30,000 people in jail,\u201d the same former special agent said. \u201cYou have to make examples of certain folks.\u201d<\/p>\n<p>This is the <em>exemplar theory<\/em> of law enforcement, a concept Blum learned from Leon Radzinowicz, the renowned Cambridge University criminologist. By Radzinowicz\u2019s estimate, about half the people in a given society follow the rules, largely because that behavior is instilled in them. Another 40 percent will commit a crime of self-interest if they\u2019re sure they can get away with it. The remaining 10 percent, according to Radzinowicz, are sociopaths, fools, and people who will do anything for cash. It\u2019s that wavering 40 percent one needs to target\u2014the more they fear prosecution, the more likely they are to do right. But \u201cif they believe they can get away with it, Katie bar the door!\u201d Blum said.<\/p>\n<p>Go after 2 or 3 percent of the lawbreakers hard enough, the theory goes, and most of the would-be criminals will fall in line. But in the sophisticated realm of offshore finance, \u201cthe whole concept just collapses,\u201d Blum told me.<\/p>\n<p>Our system has gotten so bad at uprooting and punishing major tax evaders that a kind of reverse exemplar theory has come into play. An oligarch who is tempted to evade taxes will look at the landscape and reasonably conclude that their chance of ever seeing the inside of a jail cell is basically zero.\u00a0<\/p>\n<p>Instead of pursuing actual oligarchs, the IRS and the Justice Department favor \u201copen and shut\u201d cases involving affluent professionals. \u201cTypically, it\u2019ll be a dentist who had an offshore account somewhere and they can nail him in no time,\u201d Blum said. Such indictments are often announced in advance of tax filing season as \u201can exemplar of prosecution,\u201d he explained, but the oligarchs can\u2019t relate: \u201cWhat it discourages is a lot of other dentists.\u201d<\/p>\n<p>These cases tend to be relatively simple, so as not to confuse prosecutors, judges, and jurors. The disputed sums rarely exceed a couple million bucks. And though the defendants may be 1 percenters, they won\u2019t be walking into court with a phalanx of 14 lawyers from three powerful firms. This narrow prosecutorial focus explains why the  for federal tax evasion is so miniscule (only 615 cases in 2024), why the success rate is so high (around 95 percent, with many pleading guilty), and why it is so rare to see a real oligarch in the dock, much less convicted. \u201cI used to tease the prosecutors\u2014please send me the list of all the billionaires currently serving jail time,\u201d a former IRS special agent who worked on some of the biggest tax evasion cases in US history told me. Their response: \u201ccrickets.\u201d<\/p>\n<p><span>For the rare<\/span> oligarch who gets into serious tax trouble, the IRS and the Department of Justice have proved reluctant to pursue criminal prosecutions. Attorneys often whittle strong cases down to minor civil charges, and the oligarch goes back to making billions after paying back taxes and penalties. This get-out-of-jail-free card erodes public trust in democratic institutions while emboldening other oligarchs to attempt ever-grander schemes. \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0<\/p>\n<p>Consider the case of Sam and Charles Wyly, whose initial fortune derived from their Texas data processing company, University Computing. In 2015, the IRS announced it would seek a staggering $3.2 billion in back taxes, interest, and penalties from Sam and the estate of his brother, who died in 2011 after his Porsche collided with an SUV. The brothers had evaded taxes for decades, committing their crimes, as <em>Forbes<\/em> noted, via \u201ca tangled web of offshore trusts.\u201d They also had used their wealth to influence elections to the benefit of Republican candidates. In 2004, most notably, they helped derail the presidential campaign of Sen. John Kerry by bankrolling the notorious \u201cSwift Boat Veterans for Truth\u201d ad.<\/p>\n<p>Sam, the surviving brother, spent millions building his defense team. It was money well spent. After a marathon four-year civil trial, his own $2 billion share of the IRS tab was reduced\u00a0to $1.1 billion. \u201cLet\u2019s see how much of the $1.1 billion tax bill winds up getting paid,\u201d a skeptical financial analyst wrote. Those doubts were justified. In the end, Wyly settled with the IRS for only $300 million, an 85 percent discount on the original amount. He was never charged with a crime or even faced the threat of incarceration.<\/p>\n<p>The case contains important lessons for understanding oligarchic power, and the role of the Wealth Defense Industry in making tax fraud possible and profitable. First, thanks to what the government called a sprawling \u201cscheme of secrecy,\u201d it was not the IRS but a group of computer wizards combing through data at a third-party financial institution who exposed the Wylys\u2019 illegal activities. Second, the brothers\u2019 high-priced advisers had combined secrecy and complexity in an effort to protect them: The brothers controlled 16 trusts in the Isle of Man, along with dozens of accounts and \u201c48 corporations from Nevada to the Cayman Islands.\u201d Unable to access information about offshore accounts or sort out who owned what, the only way the IRS could hope to bring a case was through informants or random luck.<\/p>\n<p>The brothers\u2019 use of professional wealth defenders also gave them a so-called reliance defense. Sam Wyly maintained that he was just following the advice of his lawyers and accountants, and it was all too much for him to understand. The litigation was so complex that one court ruling ran to 459 pages. Wyly replied with an emphatic \u201cno\u201d when asked if he had regrets or would do anything differently. And who can blame him? He sidestepped $1.7 billion in unpaid taxes and penalties and walked away a free man. Even his reputation was shielded in part by privacy provisions that bar the government from commenting on the situations of individual taxpayers.<\/p>\n<p>So much for the exemplar theory.<\/p>\n<p><span>The audacity<\/span> of the oligarchs in their legal skirmishes with the government can verge on mind-blowing. Take the private equity billionaire Robert F. Smith. In 2020, the Department of Justice issued a criminal indictment of Smith\u2019s business mentor, billionaire Robert Brockman, who made his fortune leasing software and computing terminals to auto dealerships. The government alleged Brockman had engaged for decades in a tax evasion scheme that concealed \u201capproximately $2 billion in income from the IRS\u201d in secret accounts and structures in Bermuda, Switzerland, and elsewhere.<\/p>\n<p>Smith, who also was deeply embroiled in the scheme, was able to secure a nonprosecution agreement\u2014which is \u201cunheard of\u201d in such cases, a special agent with extensive knowledge of the situation told me\u2014in exchange for his cooperation against Brockman, whom the DOJ saw as the bigger fish. (Brockman, who would plead not guilty on all counts, died in 2022, at age 81, before the government could put him on trial.)<\/p>\n<p>When it became clear the feds were onto their illegal enterprise, Smith rushed to file for amnesty through the Offshore Voluntary Disclosure Program\u2014an escape valve the IRS set up in 2009 after Blum flushed out the names of nearly 4,500 wealthy Americans evading federal taxes through the Swiss bank UBS. But with Smith and Brockman already under investigation, the application was rejected.<\/p>\n<p>Their advisers proffered another strategy: a sudden and generous campaign of high-profile philanthropy. The idea originated with Evatt Tamine, a Bermuda-based attorney who also was implicated in the evasion scheme and, like Smith, cut a nonprosecution deal with the feds. Tamine counseled Brockman and Smith that they might deflect negative legal consequences by appearing to be as charitable as possible. \u201cThese activities would work as a strong barrier against an attack from the IRS,\u201d he told them in a memo.<\/p>\n<p>The billionaires paid heed. Prior to his death, Brockman gave $25 million to the Baylor College of Medicine and millions more to Centre College and Rice University. Smith launched a much more aggressive campaign in 2016, four years before DOJ indicted Brockman and publicized its arrangement with Smith, who admitted to lying to the IRS and using offshore accounts to evade taxes for 15 years. Smith used the untaxed proceeds of his evasion scheme to set up a charitable foundation and even claimed a tax deduction for doing so. He donated $50 million to Cornell, his alma mater\u2014which named its school of chemical and biomolecular engineering in Smith\u2019s honor\u2014followed by $30 million more. <\/p>\n<p>His extensive bio on the school\u2019s website makes no mention of Smith\u2019s offenses, even though half of the latter donation came in well after they were made public. The university has showered him with alumni awards and continues to herald him as a \u201cProud Cornellian.\u201d<\/p>\n<p>Smith\u2019s pre-emptive reputational cleanse continued with a $20 million donation to the Smithsonian\u2019s National Museum of African American History and Culture. \u201cWe kept wondering, who is this Robert Smith?\u201d the museum\u2019s director of development told the <em>Washington Post<\/em>. Still largely unknown to the public, Smith made national headlines in 2019 when, while giving the commencement address at Morehouse College in Atlanta, he told the 400 elated graduates that he would be paying off their student debt\u2014$34 million in all. He also gave tens of millions to Carnegie Hall, the Susan G. Komen breast cancer research foundation, and the National Park Foundation. Another <em>Post<\/em> article cites tax experts saying that \u201cif the money in the offshore entities was going to good causes, the tax evasion might strike prosecutors and juries as less wrongful.\u201d<\/p>\n<p>Of course, if the oligarchs simply paid all their taxes, the government would have hundreds of billions more dollars every year to fund national parks, museums, the arts, universities, scholarships, medical research, and programs to address yawning social and economic inequalities\u2014goals the public has long supported. Instead, the tax gap they helped create gives lawmakers a rationale (soaring deficits!) to slash spending for those public goods. The result is a society that provides for its citizens only what the wealthy and politically connected will allow\u2014a reflection of the enormous power residing in the hands of the few.<\/p>\n<p>The Brockman\u2013Smith case was a public relations disaster from almost every angle. The biggest criminal tax fraud case in the nation\u2019s history, it could have been a shining moment of IRS and DOJ achievement and a fearsome deterrent\u2014an exemplar par excellence. Instead, the government flailed. Brockman never saw justice, and US attorney David Anderson was left with his excuses. \u201cIt is never too late to do the right thing,\u201d he\u2019d said in his press release. \u201cSmith committed serious crimes, but he also agreed to cooperate.\u201d<\/p>\n<p>And who wouldn\u2019t cooperate if it negated any criminal consequences and the only punishment was paying the original tax plus some fines? Smith\u2014who used some of his ill-gotten gains to buy two personal ski properties, luxurious homes in California and Colorado, and a commercial property in France\u2014agreed to pay $139 million in back taxes and penalties. He also agreed to \u201cabandon\u201d the $182 million in deductions he\u2019d claimed, brazenly, when he used money he\u2019d withheld from the treasury for his philanthropy binge. But these are rounding errors for a man with a $10 billion fortune.<\/p>\n<p>Americans, by and large, imagine their government as a behemoth with overwhelming power and resources, and for them it is. For the oligarchs, it\u2019s a different story. They can rest assured, knowing the government is no match for their wealth, their political investments, and the savvy professionals on their payrolls. IRS special agents devote years of their lives to cases like Brockman\u2013Smith, only to be devastated by the outcomes. One special agent who worked the case told me he was glad to have been a part of it, but the roller coaster of soaring hopes and gut-wrenching disappointments was a lot to take. \u201cIf you asked me would I do it all over again,\u201d he said, \u201cthe answer would not just be no, but <em>hell no!<\/em>\u201d<\/p>\n<p>Evasion roulette. It\u2019s a game well worth playing, if you can afford it.<\/p>\n<p><em>This article was adapted from Jeffrey Winters\u2019 book <\/em>The Blind Spot: How Oligarchs Dominate Our Democracy<em>, which goes on sale this week.<\/em><\/p>\n<\/div>\n<footer>\n<div> <i>If you buy a book using our Bookshop link, a small share of the proceeds supports our journalism.<\/i><\/div>\n<section><h3>Keep us relentless, independent, and free to read.<\/h3><p>For 50 years, <em>Mother Jones<\/em> has offered <strong>honest<\/strong>, <strong>investigative reporting<\/strong> you can rely on:<\/p>\n<p>\u00a0\u00a0\u00a0\u00a0\u2022 <strong>Relentless in the pursuit of truth<\/strong>, unafraid to hold the powerful to account<\/p>\n<p>\u00a0\u00a0\u00a0\u00a0\u2022 <strong>Independent from influence or agenda<\/strong> from oligarchs and corporations<\/p>\n<p>\u00a0\u00a0\u00a0\u00a0\u2022 <strong>Freely accessible to every reader<\/strong>, never behind a paywall<\/p>\n<p><strong>But we can\u2019t do any of this without you<\/strong>. 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