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Illustrations by Andy Rash for Money

Donald Trump, a billionaire several times over, may be the richest person ever to hold the office of president of United States. But his predecessors had plenty of wise—although sometimes controversial—advice about government and personal spending, successful careers, and what really matters to a healthy economy.

1. George Washington


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The newly created nation needed a line of credit to fund economic expansion—and to prove its creditworthiness, it needed to make good on the unpaid Revolutionary War debts incurred by the individual states. Paying them off was politically fraught, however, since a federal plan would reward speculators and favor Northern states over Southern ones. As anyone who has seen Hamilton knows, Washington chose the divisive “assumption” program put forward by his new Treasury Secretary. It was an “extraordinary” success, wrote historian John Steele Gordon: U.S. bonds were soon selling in Europe at a premium, because they were considered so safe. Confidence in the U.S. government has since helped make the dollar the peg for currencies around the world.

2. John Adams


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Respect for property rights remains a cornerstone of American law: Americans regularly protest tax hikes as a fundamental assault on their rights, and eminent domain remains a potent political issue. Yet foreign investors rush to buy U.S. assets—from New York City apartments to Treasury bonds—because they know U.S. law will respect their ownership. That’s a concept that dates back to America’s Founding Fathers, who codified it in the Fifth Amendment—noting that the government cannot seize property without “just compensation.”

3. Thomas Jefferson


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For much of its early history, the U.S. was a nation of farmers. Agricultural laborers accounted for nine-tenths of the workforce in 1790 (and roughly one-fourth as recently as 1920), and Jefferson credited planters like him with the independence, hard work, and self-sufficiency to make them ideal citizens. While farmers are now just 3% of the workforce, politicians still hail “Main Street” values and praise manufacturers and small-business owners—as opposed to greedy and decadent big-city elites—preserving at least a nod to Jefferson’s attitude.

4. James Madison


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Along with freedom and property rights, America’s colonial economy thrived on the brutal system of slavery, with farms from New York to Georgia relying on free slave labor to produce cotton, tobacco, and other crops. The nation was as conflicted on the matter as Madison himself, who owned as many as 100 slaves: The federal government had outlawed the slave trade in 1808, but, as Madison wrote to Congress, it had failed to stamp it out completely. And of course, slavery itself was still legal in Southern states until the Civil War.

5. James Monroe


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Real estate bubbles are nothing new, and Monroe was president during the new nation’s first one. The purchasers Monroe referred to had borrowed heavily to buy Western lands from the federal government, then struggled to repay when crop prices plunged. Monroe was sympathetic to the debtors, but not everyone shared his view. The question persists in economists’ discussion of “moral hazard”—the notion that forgiving irresponsible behavior will induce more of the same.

6. John Quincy Adams


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Adams had wealth, sophisticated tastes, a worldly existence, and public acclaim. Son of a president, he grew up accompanying his father on diplomatic missions, became an envoy to the Netherlands before turning 30, then served as President himself. He was also a noted abolitionist and a published (if somewhat mediocre) poet. But as Adams reminds us, it’s hard to satisfy the human desire for more. In his 1841 poem “The Wants of Man,” the speaker itemizes his desire for fancy meals, “elegant attire,” love, power, and adulation, but also confesses: “And were each wish a mint of gold / I still should long for more.”

7. Andrew Jackson


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Donald Trump isn’t the first President to rail against entitled, out-of-touch federal bureaucrats. During Jackson’s eight-year tenure, he removed up to a fifth of government workers, who, he argued, had acquired “a habit of...tolerating conduct from which an unpracticed man would revolt.” The problem? Jackson replaced them with his own, often more corrupt, political supporters. Other Presidents imitated Jackson’s “spoils system” of rewarding party hacks with government jobs, eventually inspiring a new reform movement.

8. Martin Van Buren


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In the early 19th century, Americans were routinely jailed for being unable to repay loans. Van Buren and other reformers, however, argued that debtors’ prisons were not only unfair, but counterproductive, making it less likely the debtors would get back on their feet. Such punishment largely disappeared before the Civil War, but a debate continues over how much personal responsibility individuals should bear for their financial misfortunes. Academic studies—including ones written by now-Senator Elizabeth Warren—that blame big medical bills for many modern bankruptcies are a frequently cited argument in favor of the Affordable Care Act.

9. William Henry Harrison


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Income inequality isn’t a new concern. The campaign of 1840 was fought during a depression that had lasted three years and would go on for another four, and Harrison ran on a platform of financial reforms—reestablishing a central bank to shore up the economy and eliminating Jackson’s spoils system, which had already come to be associated with corruption. He would die in office after just a month, making his campaign promises moot. But many—like economist Thomas Piketty, whose 2013 tome Capital was a surprise bestseller—still worry that our economic system tends to amplify inequality.

10. John Tyler

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The complex U.S. relationship with Mexico dates back to the 19th century. Tyler worked hard to bring the fledgling Texas republic—newly independent from Mexico—into the union, signing a bill offering annexation during his final days in office, and showing a prescient appreciation for Texas’s economic potential. But the annexation of Texas also fueled what has become an ongoing conflict between the U.S. and Mexico over trade and management of the border.

11. James K. Polk


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Polk served for just one term but is often regarded as one of the most effective Presidents, in part because he was a workaholic. “Pursue a vision, but mind the details,” the Harvard Business Review recently noted in summation of his management style. He set a small number of clear goals—acquiring California from Mexico, and Oregon from Great Britain, reorganizing the Treasury and lowering the tariff—and pursued them single-mindedly until they were largely achieved. While more recent Presidents have faced criticism over vacation plans and leisure pursuits, it’s worth noting that the strains of office wore Polk out entirely: He died within months after retiring.

12. Zachary Taylor


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Anyone who has heard the term ’49er has a sense of the possibility and excitement that gripped Americans during Taylor’s short time in office. Taylor, who used his single annual message to Congress to call for a transcontinental railroad, saw California’s limitless potential. Taylor died a year into his term—but California’s white population would balloon from 15,000 in 1848 to more than 300,000 by 1860. And the transcontinental railroad, which was eventually completed in 1869, opened East Coast markets to California food and minerals.

13. Millard Fillmore


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Before Fillmore was President, he was a U.S. congressman whom Samuel F.B. Morse impressed with “a rude model” of what would become the telegraph. Fillmore wrangled $30,000 ($880,000 in today’s dollars) in federal funds to help build an experimental line between Washington and Baltimore—an innovation that would come to radically remake communications. From space satellites to the Internet, the government has continued to play a key role in promoting technology and infrastructure that help private businesses transform the economy.

14. Franklin Pierce


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Conservative politicians have been echoing this complaint ever since Pierce made it in 1853. At that time, before the introduction of personal and corporate income taxes, the federal government’s annual revenue was $59 million, or about $1.8 billion in today’s dollars—mostly from import duties and the sale of public lands. Compare that to 2016, when tax collectors brought in an estimated $3.3 trillion. Of course, the federal government has also created several new programs since Pierce’s time—from Social Security to the Air Force. Federal spending has gone from less than 2% of GDP in Pierce’s time to more than 20% today.

15. James Buchanan


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Like many U.S. Presidents, Buchanan believed in “manifest destiny”—the idea that white settlers must extend “the blessings of Christianity and of civil and religious liberty over the whole North American continent.” Getting rich was, of course, also part of the bargain. Buchanan was right in one sense: Holding back the economic forces that propelled settlers along the Oregon and California trails was probably futile. But as we now appreciate, America’s westward drive came at devastating human cost—in particular for the Native Americans who were uprooted from their lands and forcibly resettled on reservations.

16. Abraham Lincoln


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While Lincoln himself is widely beloved, he created two institutions Americans love to hate: the income tax and a forerunner of the Internal Revenue Service to collect it. Lincoln’s tax, instituted to fund the Civil War, was progressive—the first $600 in earnings were exempt—and relatively light, with rates that topped out at 5% of income. The tax was repealed a decade later, although the 16th Amendment brought it back in 1913. Even Lincoln acknowledged the system’s imperfections: “If we should wait before collecting a tax to adjust the taxes upon each man in exact proportion with every other man, we should never collect any tax at all.”

17. Andrew Johnson


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While modern politicians play up their folksy roots, Andrew Johnson was the real deal. Like Lincoln before him, Johnson was born in a log cabin. Apprenticed to a tailor at 10, he did not learn to write or do basic math until he was 18. He is believed to have been drunk when he delivered his rambling, defensive vice presidential speech, quoted above, which dumbfounded his audience and left him humiliated. While his humble roots helped him connect with voters, his clumsy heavy-handedness undermined his presidency, leading to bitter battles with Congress and undermining federal efforts to rebuild the South and enfranchise former slaves.

18. Ulysses S. Grant


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It’s now widely considered one of the best pieces of writing by a President —but Grant’s autobiography emerged out of financial necessity. Several years after retiring from the Oval Office, the President and general who had outmaneuvered wily Confederate leader Robert E. Lee fell prey to a fraudulent investment scheme, losing his family’s fortune. Determined to provide for his heirs, Grant (who may have been speaking with a touch of false modesty) resolved to write his memoirs—even as he fought the cancer that would eventually kill him—and the resulting volume, published by Mark Twain, became a bestseller.

19. Rutherford B. Hayes


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As the economy leapt into the industrial age, violent labor battles became a more frequent occurrence. Hayes used federal troops to maintain order during “the Great Railroad Strike”—a disturbance prompted when the Baltimore & Ohio Railroad announced a 10% pay cut—which grew to involve 100,000 workers and led to as many as 100 deaths. While Hayes’ intervention aided the railroads, 19th century working conditions were indeed unjust and oppressive—certainly by 21st century standards—and workers didn’t win significant improvements in pay and working conditions until the Progressive Era.

20. James Garfield


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Garfield worked as a schoolteacher before joining the Union Army and later entering politics. He continued to believe in the power of education to let Americans climb the economic ladder—particularly for poor blacks struggling to escape both the legacy of slavery and the South’s emerging Jim Crow system. As a Congressman, he helped create a forerunner to the Department of Education. And in his inaugural address he proposed a federally funded program to promote “universal education.” He was shot and killed months into office—and the federal government did not commit to African-American education in the South for another 70 years.

21. Chester A. Arthur


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Late 19th-century immigration debates sound shockingly familiar. The arrival of thousands of Chinese workers—drawn largely by the Gold Rush and construction of the transcontinental railroad—bred resentment among white Americans, who blamed them for crime and lower wages. In 1882, Congress passed a bill to bar Chinese immigration for 20 years. Arthur vetoed it, defending Chinese Americans: “The States of the Pacific Slope are full of evidences of their industry.” Yet after a number of Western towns burned the President in effigy, Arthur relented—signing a second bill that shortened the exclusion period to 10 years. Large-scale Asian immigration to the U.S. would not resume again until the 1960s.

22 & 24. Grover Cleveland

1885-1889, 1893-1897

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The question of whether bureaucrats should be career professionals or political flunkies continued to plague officeholders. The recent Pendleton Act had mandated competitive exams for at least some federal offices—but critics claimed the standardized tests unfairly favored wealthy, polished applicants. Cleveland rode a wave of reform, campaigning on his own personal rectitude, but wound up wavering on staff appointments—he avoided unnecessary firings of competent Republican officials, but favored Democrats as opportunities arose. The stance fully pleased neither reformers nor partisans, arguably costing Cleveland reelection in 1888.

23. Benjamin Harrison


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American manufacturing workers were struggling. Believing that import tariffs would aid workers, by protecting them from low-cost competition abroad, Harrison signed a tariff that lifted import duties nearly 50% on many goods. Opponents argued the move would backfire by raising the costs of goods for many of the poor workers it was trying to help. Sound familiar? The tariff proved unpopular, and Harrison lost his reelection bid to Grover Cleveland, whom he’d defeated four years before.

25. William McKinley


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The election of 1896 was literally about money. McKinley favored the gold standard—a dollar peg to a fixed amount of gold—to restrict the supply of money and therefore promote stable prices. Rival William Jennings Bryan wanted a looser “bi-metal” standard, with gold and silver, to allow for more inflation. (Inflation was good news for millions of debt-ridden farmers who knew devaluing the dollar would make it easier to pay back loans.) McKinley’s victory put the U.S. on the gold standard, which would survive until the Great Depression. Today, mainstream economists favor neither gold nor silver. But inflation questions—how much is beneficial, and who benefits—continue to vex policymakers.

26. Theodore Roosevelt


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As America evolved into an industrialized nation, corporations took on new dominance—shaping what Americans bought and ate, how long they worked, and what wages they earned. Many middle- and working-class Americans began to seek a bulwark against this overwhelming power; “progressives” like Roosevelt delivered. Among his accomplishments: breaking up monopolies, including one of the nation’s largest railroads; strict new rules for inspecting meat and medicine; and the creation of dozens of national parks and forests.

27. William Howard Taft


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How far should the federal government go to promote fairness? As Americans came to accept Washington’s new role as economic referee—balancing the interests of corporations, workers, and consumers—Roosevelt’s handpicked successor continued many progressive policies. Yet Taft had a friendlier attitude toward business and a more restrained vision of the federal government than his mentor. Taft argued that Washington should focus on laws to promote “equality of opportunity,” rather than outcomes—an argument many conservatives make to this day.

28. Woodrow Wilson


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The Federal Reserve Bank wasn’t signed into existence until 1913—before which Americans suffered through a century of boom-and-bust cycles. (A successor to the bank created by Hamilton and Washington was abolished by Andrew Jackson.) One big problem with private banks: In bad times, they tended to hoard money to protect their own balance sheets, rather than lend it out to help struggling businesses. After the Panic of 1907, Wilson proposed a national bank that would do the opposite—helping keep interest rates low in difficult times and then raising those rates when the economy seemed likely to overheat.

29. Warren G. Harding


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Harding was what today we might call an “unreconstructed male”—complete with weekly White House poker parties and a mistress and love child. But he was also the first President elected with women going to the polls across the U.S.—and he recognized that government had to meet women’s needs. He called for (and signed) a maternity bill that helped fund health clinics in rural areas. While the program was ended in 1929, a 2012 study concluded it effectively reduced infant mortality in the 1920s.

30. Calvin Coolidge


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Coolidge saw business as America’s animating spirit: “Americans,” he said, “are profoundly concerned with producing, buying, selling, investing, and prospering in the world.” Indeed, the 1920s were a decade of remarkable material aspiration. For the first time, ordinary Americans owned telephones, washing machines, radiosand stocks. Coolidge’s business–friendly administration balanced the budget, reduced the national debt and sharply cut taxes. And the Dow in turn rose more than 250%—more than under any other 20th-century President. Of course, this sunny materialism also had a dark side, although it wouldn’t come to light until Coolidge was out of office.

31. Herbert Hoover


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The 1929 stock market crash was followed by a slew of bank closures, and the world economy began to sink. Suddenly what had seemed like sunny competence began to sound glib: Like many successful people, Hoover may have failed to appreciate how many of his accomplishments were due to tailwinds of favorable circumstance. Yet the wealthy President does not entirely deserve his out-of-touch reputation. He ran humanitarian operations that fed millions during and after World War I. And as President, he undertook activist programs that would later be associated with Roosevelt, pressing business for higher wages and promoting job-creating public works like the Hoover Dam. There were also mistakes, however—like the Smoot-Hawley Tariff Act, which most economists say choked off trade and made a bad situation worse.

32. Franklin D. Roosevelt


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At the height of the Great Depression, unemployment hit 25%. Yet Roosevelt was a skilled communicator who excelled at conveying confidence and optimism. During his first 100 days in office, he spurred a flurry of legislation—stabilizing the banking system, supporting crop prices, and creating thousands of jobs building roads and bridges. Today, historians consider the "New Deal" a mixed success. The government-funded tactics Roosevelt used to jumpstart growth are ones policy-makers still use today. (President Trump has frequently talked about a $1 trillion infrastructure plan to put Americans back to work.) But overall the economy remained lackluster until the outbreak of World War II, and the resulting spike in U.S. military spending.

33. Harry S. Truman


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The critics who cried foul at Barack Obama’s recent $400,000 speaking fee might well have found an ally in President Truman. He commanded no federal income after he left office beyond his $113-a-month Army pension—and, despite lucrative offers, refused to capitalize on his public service beyond selling his memoirs. His situation did improve in 1958, when Congress passed the Former Presidents Act, awarding ex-Presidents a lifetime pension and Secret Service protection. More modern cash grabs did not begin until Gerald Ford, who accepted posts on corporate boards and began giving paid speeches; Ford’s example has been followed by every President since.

34. Dwight D. Eisenhower


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The last general to serve as President cautioned against the creeping scope of the military—and, in particular, Big Government’s tendency to collude with powerful industry to further their mutual growth. Last year, the federal government spent $584 billion on the military and another $68 billion on veterans' benefits, compared with $91 billion on transportation and $92 billion on education. In all, defense accounts for roughly half of the “discretionary” federal budget, which excludes obligations like Social Security, Medicare, and interest on the national debt.

35. John F. Kennedy


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The privileged son of a prominent businessman, Kennedy believed he could serve as an honest broker between capital and labor. But he became enraged after U.S. Steel broke a promise by raising prices after unions agreed to limit wage demands. Kennedy faced a “paradox,” Wall Street Journal columnist Peggy Noonan recently noted: Business leaders whom he admired as “bright and enlightened” in private life frustrated him by pursuing selfish, short-term ends at the helm of their corporations.

36. Lyndon B. Johnson


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Many Americans share Johnson’s dream of a nation committed to generosity rather than aggression. But like Johnson, we frequently fall short. His vision of a “Great Society” secured the right to vote for black Americans, and launched economic programs that Americans now cherish: Medicare, Medicaid, Head Start, food stamps, and others. Yet Johnson’s domestic efforts competed budgetarily with the escalating fight in Vietnam. Afraid of jeopardizing his anti-poverty programs, Johnson attempted to fund his budget with deficit spending. The resulting runaway inflation would, over the next decade, come to bedevil his successors.

37. Richard M. Nixon


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Two decades before Watergate, Nixon was nearly felled by another political scandal. He was serving as Dwight Eisenhower’s running mate when opponents charged that he was using political contributions from wealthy donors to live “in style far beyond his salary,” as one headline put it. Nixon responded with a nationally televised half-hour address, in which he laid bare his family finances in excruciating detail. It’s easy to smirk now at the aw-shucks style of what came to be called the “Checkers” speech (after the Nixon family dog). But Nixon’s version of what we might today call a “celebrity confessional” saved his career, at least in the short term—and heralded the power of television in national politics.

38. Gerald R. Ford


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Since the Progressive Era, many Americans have looked to Washington to solve social problems—handing bureaucrats more money and more power over daily life. Ford, who worried that federal spending was contributing to runaway inflation, pressed for more limited government, telling Congress, “The first thing we all have to do is to learn to say no.” Many Americans still want it both ways. President Trump won the 2016 election in part by promising hefty tax cuts—but also pledging to protect Social Security and Medicare and boost defense spending. At least one nonpartisan analysis found such changes would increase the federal debt by more than $5 trillion over the next decade.

39. Jimmy Carter


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Materialism was overtaking the country, Carter warned in his “Malaise” speech: “Human identity is no longer defined by what one does, but by what one owns.” He fretted aloud over Americans’ stagnant productivity, unwillingness to save for the future, and declining respect for institutions like schools and the news media—critiques that still ring true today. Yet while Carter may have diagnosed the problem, his emphasis on self-sacrifice (such as minding the 55 mph speed limit) failed to resolve domestic woes, and his scolding tone put off voters.

40. Ronald Reagan


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By the 1980s, Roosevelt’s once-radical New Deal had softened into conventional wisdom: Americans now expected Washington to take an active role in shaping the economy. Regulations prodded “good” behavior by powerful businesses, and hefty income taxes (top rates were 70% when Reagan took office) promoted fairness. But Reagan, a former Democrat, became convinced that these efforts were shackling America’s entrepreneurial spirit. “Government is not the solution to our problem; government is the problem,” he liked to say. If we focused on growing the economy—lower taxes, less red tape—rather than redistributing wealth, everyone would be better off, he argued. Economists still debate the effectiveness of Reagan-era reforms, but he presided over a remarkable boom.

41. George H. W. Bush


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Reagan’s success helped make tax cuts Republican gospel. His successor’s single term revealed some of their limits. Bush had been a prominent critic of one of Reagan’s suggestion that tax cuts would grow the economy enough to pay for themselves, dubbing it "voodoo" economics. Yet eight years later, on the cusp of the presidency himself, Bush doubled down on Reagan’s cuts. In 1990, faced with a ballooning deficit, he relented and supported a tax hike to help balance the budget—a pragmatic approach now lauded by economists. But the flip-flop, which became a mainstay of attack ads, helped cost him the presidency in 1992.

42. William J. Clinton


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This message from “the man from Hope” resonated deeply with voters in 1992; it remains an articulation of how most of us believe the economy should work. In hindsight, though, it feels overly optimistic. During the past generation, market forces have prodded U.S. corporations to lay off millions of workers, while hiking CEO pay in the name of “shareholder value.” Wall Street firms paid traders millions for their supposed financial acumen, only to demand government bailouts when investment bets went bad. And Silicon Valley executives like Steve Jobs have made billions of dollars bragging that “it’s better to be a pirate than join the Navy.”

43. George W. Bush


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In late 2008, George W. Bush tried to ward off a global financial panic following the collapse of investment bank Lehman Bros. This plainspoken assessment came as Congress failed to pass the $700 billion bailout he had requested. Lawmakers eventually relented, helping the nation avoid economic catastrophe. Bush exited office with historically low approval ratings due to both the Iraq War and the financial crisis. A few months later, the stock market hit bottom and began to rebound.

44. Barack Obama


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Is the economy basically a team sport or solo competition? As Obama saw it, the economy was not made up of hero entrepreneurs, nor Jeffersonian planters, reaping the rewards of toil and self-reliance. It was a community in which everyone plays a crucial part. His biggest legislative achievement, Obamacare’s promise of health coverage for every American, underscores that ethos. Yet during the same speech, which also echoed an Elizabeth Warren theme, Obama went on utter a less apt phrase: “If you’ve got a business, you didn’t build that. Somebody else made that happen.” His opponents pounced, arguing he was dismissing individual achievement. The question continues to divide us.

45. Donald J. Trump


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Trump came into office making big promises—but, as he noted in the preceding quote (from his best seller, The Art of the Deal), at a certain point you’ve got to produce results. After his first attempt at repealing and replacing Obamacare stalled out, it became clear: This stuff is complicated. With a health care bill finally having passed the House and currently awaiting action from the Senate, and tax reform scheduled next, Americans are watching to see if Trump can deliver the goods.