PDF Summary:Confronting the Presidents, by Bill O'Reilly and Martin Dugard

From revolution to recession, scandal to triumph, America’s presidents have shaped the nation’s story in ways both inspiring and contentious. In Confronting the Presidents, journalists Bill O’Reilly and Martin Dugard pull back the curtain on the personal struggles and political gambits of every US president—revealing the human flaws and fierce convictions behind the Oval Office.

Our guide to Confronting the Presidents focuses on ten presidents that O’Reilly and Dugard suggest were particularly influential or controversial: George Washington, Andrew Jackson, Abraham Lincoln, Ulysses S. Grant, Theodore Roosevelt, Franklin Delano Roosevelt, John F. Kennedy, Richard Nixon, George W. Bush, and Barack Obama. These presidents come from different eras of American history, representing a broad overview of the nation’s biggest challenges and the leaders who navigated them. Through our commentary, we’ll provide additional context around their decisions and legacies.

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(Shortform note: The effectiveness of Grant’s Reconstruction efforts is a source of controversy among historians. Some argue that the governments he set up in the South were ineffective and corrupt, with politicians scamming the federal government and their constituents to enrich themselves. Others argue that this corruption was standard for the era, and that Grant’s reconstruction enabled the first period of multi-racial democracy in the country’s history.)

Grant’s presidency also saw continued westward expansion and its consequences, both positive and negative. On the positive side, Grant oversaw the creation of the first national park at Yellowstone and the completion of the transcontinental railroad. On the negative side, increased expansion meant more conflicts with American Indians, despite Grant’s efforts at mediation.

(Shortform note: Historian Roxanne Dunbar-Ortiz (An Indigenous People’s History of the United States) explains that as the US expanded into and industrialized the western side of the continent, it passed more anti-Indian policies. The growth of the country’s rail network required a lot of land, and the US government was willing to break its treaties with American Indian tribes to force the Indians off their territory and give it to railroad companies.)

O’Reilly and Dugard write that while Grant was an honest man who maintained a good reputation throughout his presidency, his administration was plagued by corruption. Scandals like the Whiskey Ring involved the people around Grant using federal money to enrich themselves and their friends.

(Shortform note: The Whiskey Ring refers to a group of midwestern government officials, Republican politicians, and whiskey distillers who conspired to cheat the federal government from 1871 to 1876. They used their connections, along with bribes and blackmail, to under-report the amount of whiskey made and distributed by distilleries, saving them a great deal of money on taxes that was then paid out to the ring itself.)

Part 3: The Progressive Era

Now that we’ve covered the presidents who guided the US through the Civil War and its aftermath, we’ll skip ahead several decades. Following a series of relatively hands-off administrations, the Progressive Era saw presidents taking a more active approach to politics. In this section of the guide, we’ll examine two presidents who set the tone for this period: Theodore Roosevelt and Franklin Delano Roosevelt.

(Shortform note: There are significant differences between what we call progressives today and politicians of the Progressive Era. Early 20th century progressives were far less concerned with issues like wealth inequality, racial justice, or a non-interventionist foreign policy. Instead, they focused their efforts on regulating big businesses, consumer protection laws, and stopping corruption among government bureaucrats.)

The 26th President: Theodore Roosevelt

O’Reilly and Dugard write that Theodore Roosevelt became president at the end of the Gilded Age, a time when unregulated corporations expanded massively in wealth and political power. Roosevelt believed these corporations had gone too far and that the government had to step in. This section will go over Roosevelt’s personality and life, as well as his major political accomplishments.

Personal Life

Roosevelt was born into a wealthy New York City family, though he always preferred sports and outdoor activities to education and high society. When he was a young man, Roosevelt’s wife and mother both died within a short period of time. Full of grief, Roosevelt moved to North Dakota to live on an isolated ranch. There, he adapted to the harsh lifestyle of the American West and developed the belief that the country should be run according to rugged, masculine values like strength, courage, and determination. The authors say he lived by these ideals himself during the Spanish-American War, when he gathered and led a regiment of volunteers known as the Rough Riders, who earned distinction for their bravery in battle.

(Shortform note: For an example of Roosevelt’s ideals, we can look to his support of American football. A football player and fan, Roosevelt believed the sport helped young men develop rugged, masculine qualities. During a wave of controversy over injuries suffered during college football games, Roosevelt brought together the football coaches of several major schools to encourage them to reform the game by banning excessively violent, unsportsmanlike conduct. This meeting helped create the Intercollegiate Athletics Association, a precursor to the modern National College Athletics Association, or NCAA.)

After his military service, Roosevelt returned to politics and concerned many of the high-up politicians and businessmen in the Republican Party with his popularity and strong anti-corruption stance. O’Reilly and Dugard write that these power brokers offered Roosevelt the vice presidency under President McKinley to keep him in a position without much real power. But in 1901, an assassin killed McKinley, and Roosevelt was suddenly president.

(Shortform note: In Roosevelt’s time, the nomination process for presidential and vice presidential candidates had less to do with popular will and more to do with party politics and backroom deals. Primary elections for presidential candidates were in their infancy, meaning a majority of delegates didn’t choose nominees based on the choices of voters. Instead, they voted based on deals, negotiations, and their allegiances to candidates or factions. Presidential primaries became commonplace within two decades of Roosevelt’s election, though the vice presidential candidate isn’t elected via primary to this day.)

Presidency

As President, Roosevelt was energetic and ambitious. The authors explain that for his domestic agenda, he started the country’s first wave of corporate regulations to protect public health, the environment, and competition in the free market. This included creating the Food and Drug Administration to ensure the cleanliness and safety of food and medicine and having his Department of Justice pursue antitrust laws to break up corporate monopolies. Roosevelt also created some of the country’s first environmental protections through agencies like the Forest Service.

(Shortform note: Roosevelt was known as the “trust-buster” for his efforts to break up large corporate monopolies, also known as trusts. But he didn’t do so indiscriminately—he focused on monopolies he felt were charging unfair rates and left other trusts alone. In fact, when Roosevelt’s successor William Howard Taft pursued trust-busting cases more universally and indiscriminately, Roosevelt criticized him. This difference, among others, eventually led Roosevelt to split off from the Republican Party and form the Bull Moose Party.)

Internationally, Roosevelt made a point of projecting America’s power and prestige across the globe. His biggest project was the Panama Canal, a massive structure that connected the Atlantic and Pacific oceans. Roosevelt also brokered a peace deal to end the Russo-Japanese War in 1905, winning a Nobel Peace Prize for his efforts and highlighting the US as a major player on the global political stage.

(Shortform note: Roosevelt became president during America’s rise as an international empire. For much of the 19th century, the nation was mainly concerned with its own problems and lacked the power to influence other countries, unlike European empires. But as the country grew and prospered in the late 19th century, the US used a combination of violence, diplomacy, and economic pressure to influence its neighbors. For example, the Banana Wars were a series of conflicts that saw the US pressuring and invading multiple countries in Central America to secure favorable arrangements for the American fruit companies operating there.)

The 32nd President: Franklin Delano Roosevelt

Two decades after Theodore Roosevelt left office in 1909, his fifth cousin, Franklin Delano Roosevelt, or “FDR,” began the longest term of any US President to date. FDR became president during the Great Depression, the worst economic crisis in world history. Meanwhile, tensions in Europe between democratic, fascist, and communist nations were on the rise. O’Reilly and Dugard argue that, because of the way FDR handled these developments, he’s undoubtedly the most impactful president in modern American history, even though his legacy is complex and imperfect. They elaborate on the president’s character and the controversies of his presidency.

(Shortform note: FDR also became president during a moment when the American people didn’t trust the government. His predecessor, Herbert Hoover, was widely disliked for his inability to respond effectively to the Great Depression and for sending the US Army to attack the Bonus Army, a group of World War I veterans demanding to receive their cash bonuses for serving early. The Bonus Army, along with other protests and labor actions, reflected an environment of desperation and mistrust—not an easy thing for a new president to deal with.)

Personal Life

Much like his cousin Theodore Roosevelt, FDR was born into wealth. After receiving a prestigious education at Harvard, he married his distant cousin Anna Eleanor Roosevelt—a woman who went on to have a long, accomplished career of her own as a diplomat and activist. O’Reilly and Dugard explain that their marriage was distant, with the pair sharing little affection and living their lives separately.

(Shortform note: Some scholars argue that FDR’s marriage to Eleanor was distant in part because the First Lady may have been a lesbian. Eleanor exchanged emotionally intimate (but not explicitly romantic) letters with journalist Lorena Hickok between 1932 and 1938, and Hickok gave up her newspaper job for a White House staff position around this time. This has led some historians to speculate that the two were having an affair.)

According to the authors, FDR was ambitious and intellectual, and he enjoyed solitude. He was also plagued by health problems. At 39, he caught a rare adult case of polio that left him mostly wheelchair-bound. However, he trained himself physically and pushed himself to stand and walk during public appearances. Once the US entered World War II, the strain on FDR’s body increased. He slept less, using the extra time to meet with his advisors and plan. He lost weight and became weak. These stresses, combined with FDR’s lifelong smoking habit, caused his death in office at 63 by cerebral hemorrhage.

(Shortform note: FDR’s health problems were kept secret from the public for his entire political career. He didn’t use his wheelchair in public, fearing his political opponents would say he wasn’t physically fit to be president. He also only kept doctors on staff whom he knew would keep quiet about his health problems. This meant that until only a few months before his death, a majority of people didn’t even know he was unwell.)

Presidency

O’Reilly and Dugard largely discuss FDR’s time in office through two major events: The Great Depression and World War II.

The Great Depression was ongoing when FDR entered office, and he attempted to stabilize the economy through a variety of new federal programs known as the New Deal. The New Deal aimed to build safety nets for the poor, create thousands of new jobs, and restore consumer confidence with projects ranging from bailouts for banks to the creation of Social Security and investments in public works projects. FDR used his control over both houses of Congress and pushed the limits of his executive power to pass the New Deal. His critics compared his left-leaning policies and desire for power to Soviet dictator Joseph Stalin. But FDR remained popular, easily winning re-election in 1936, and the economy slowly recovered.

(Shortform note: The Great Depression was a global economic crisis that began in 1929 and lasted until around 1941. An economic boom in the 1920s led to widespread stock market speculation and borrowing on credit. Eventually, this bubble burst—people realized their investments were worth far less than they’d paid for them, and creditors realized their debtors couldn’t pay them back. This led to widespread poverty and unemployment as massive amounts of wealth disappeared overnight. When FDR entered office, he didn’t know how to fix this problem—the “New Deal” wasn’t even a coherent plan yet. He just knew he had to use government power to repair the economy, as opposed to the hands-off approaches of the past.)

O’Reilly and Dugard explain that during the first half of his presidency, FDR tried to take a mostly neutral stance on the rise of communism in the Soviet Union (USSR) and fascism in Germany and Italy—despite growing news of human rights abuses in these countries. But when World War II began in 1939, FDR gradually changed course and supported Allied nations like France and the UK, providing resources like diplomatic pressure and weapon shipments. Eventually, this support caused the Empire of Japan—part of the Axis powers along with Germany and Italy—to launch a surprise attack on the US and bring it into the war.

(Shortform note: FDR opposed the Axis powers from the moment the war began in 1939. However, he lacked the political support to go to war. Many Americans believed the conflict was a European and Asian affair, and that the US should have nothing to do with it. But as the war expanded in 1940 and 1941, public opinion gradually shifted. Still, FDR felt he lacked the support to sustain a widespread war. Instead of joining outright, he supported the Allies economically and placed heavy sanctions on the Axis powers. These sanctions eventually pushed the Japanese Empire to attack the US at Pearl Harbor in December 1941—giving FDR the widespread support he needed to go to war.)

FDR delegated most military decision-making to his generals, focusing on politics and diplomacy instead. O’Reilly and Dugard note that he made his most controversial decisions during this period, from imprisoning thousands of innocent Japanese Americans in internment camps to ignoring Holocaust victims in Nazi concentration camps in favor of trying to end the war quickly. He also grew to trust Stalin and wanted to peacefully divide influence over Europe between the US and the USSR—a move that O’Reilly and Dugard argue allowed the Soviets to occupy and oppress much of eastern and central Europe. FDR remained popular regardless, becoming the first and only president to be elected to four terms in office.

(Shortform note: Historians continue to debate FDR’s decisions regarding the Holocaust. His defenders argue that FDR believed he could save more lives by ending the war quickly and effectively than he could by sending the army to liberate Nazi concentration camps. His detractors believe that FDR simply wasn’t that concerned about the loss of Jewish life—they argue that he knew about the Holocaust long before the US army ever liberated any concentration camps, but didn’t prioritize ending the genocide because of his or his administration’s anti-semitism.)

Part 4: The Cold War

After the end of WWII, the US and the USSR were global superpowers, and both nations engaged in a “Cold War” of economic and diplomatic competition along with espionage and warfare through proxy groups. The authors write that America’s power, along with the constant threat of nuclear war, meant that the role of president was more important than ever. In Part 4 of our guide, we’ll cover two presidents who took on these challenges in very different ways: John F. Kennedy and Richard Nixon.

(Shortform note: As American military power expanded, so did the power of the presidency. For the first time in American history, presidents could overthrow foreign governments, fight covert wars, and even use nuclear weapons without congressional approval. In addition, new executive agencies gave the president more direct power over the enforcement of laws, meaning they had greater domestic influence as well. This means that in the post-World War II era, American presidents have more tools at their disposal than ever.)

The 35th President: John F. Kennedy

John F. Kennedy, or “JFK,” was the youngest man ever to become president. He took office during one of the most tense moments in the country’s history, as the Cold War threatened to heat up. JFK was a figure known for both his personal popularity and his tragic death via assassination in 1963. But O’Reilly and Dugard emphasize that beneath JFK’s clean-cut image was a chaotic personal life and a political career full of controversy.

(Shortform note: A big part of JFK’s popularity and image came from his and his family’s youth, charisma, and social standing. The Kennedys were glamorous, high-class, and spent a lot of time around celebrities. All of this made the public follow their lives more closely than other first families—and it turned JFK into the first “celebrity president,” whose show business strategies would inspire future generations of politicians.)

Personal Life

JFK was born in 1917 to an influential political dynasty. His father, Joseph Kennedy—a wealthy financier and ambassador with many political connections—favored JFK’s older brother Joe Jr., grooming him for political office from a young age. Meanwhile, JFK suffered from a number of medical problems in his youth. These included chronic back pain, which led to a painkiller addiction for much of his life. When Joe Jr. died serving in WWII—O’Reilly and Dugard note that both he and JFK served despite their family’s ties to and sympathy for Adolf Hitler—Joseph decided JFK would run for office instead, spending vast sums of money on JFK’s campaigns for Congress and eventually the presidency.

(Shortform: The Kennedy dynasty’s connection to Nazi Germany remains controversial among historians. Those who believe it exists point to JFK’s father Joseph Kennedy’s personal anti-semitism, strong stance against joining World War II, and his habit of undermining FDR’s administration during his ambassadorship—he gave interviews that contradicted the president and even argued that the Allies should surrender. Defenders of the Kennedy family argue that any potential sympathies toward fascism don’t extend beyond the family patriarch, and that JFK and his brother Joe Jr.’s service in World War II disproves their potential fascist stances.)

While the public knew JFK as an honest, handsome young man with a happy, loving family, O’Reilly and Dugard explain that this wasn’t the case in private. They explain that JFK had countless marital affairs to the point where his promiscuity was an open secret in Washington. He even made passes at the wives of the people around him and was known as a “playboy.”

(Shortform note: JFK’s sex scandals were connected to some of the other unsavory rumors that surrounded him—namely, his and his family’s alleged ties to organized crime. One of JFK’s affairs was with Judith Campbell, a woman closely tied to powerful mobsters like Sam Giancana and John Roselli. The FBI director at the time, J. Edgar Hoover, even voiced his concern about Campbell’s access to the president, concerned she could be influencing him.)

Presidency

O’Reilly and Dugard mainly focus on JFK’s foreign policy, which had two major challenges to manage. First, America’s ally South Vietnam was struggling with domestic unrest against its oppressive leader, President Ngo Dinh Diem. The country was also under attack from communist revolutionaries in the north. JFK didn’t want to expand American involvement in Vietnam, but he didn’t want to be seen as weak on communism either. O’Reilly and Dugard argue that JFK chose to take a middle path instead—ordering the CIA to assassinate Diem in the hopes that it would stabilize the situation.

(Shortform note: The split of Vietnam can be traced back to World War II, when the entire country was a French colony. During the war, Japan invaded and occupied Vietnam. Vietnamese communist rebels known as the Viet Minh fought the Japanese and declared the country independent after Japan’s defeat. France attempted to retake the country after the war, but failed. As part of the peace settlement, the French remained in the south while the Viet Minh held the north, and national elections were planned to unify the country under one government. Fearing the Viet Minh would win, the South Vietnamese government refused to hold these elections, and the situation eventually devolved into civil war.)

JFK’s second major challenge was in Cuba, where a recent revolution led by Fidel Castro had created a communist government allied with the USSR. JFK approved a CIA plan to arm and train Cuban dissidents to invade Cuba via the Bay of Pigs and overthrow Castro in 1961. The plan failed disastrously, and the public and press blamed JFK. The following year, JFK entered a tense standoff when the USSR attempted to move nuclear missiles to Cuba—eventually forcing Soviet leader Nikita Khrushchev to back off.

(Shortform note: US-Cuba relations remain tense to this day, with the US maintaining a wide variety of economic sanctions on the island nation. The nature of these sanctions has shifted over time—President Obama famously took steps toward normalizing relations with Cuba, though President Trump walked these measures back soon after. What’s remained consistent is the American stance that the communist Cuban regime must be replaced with a democratic, capitalist one.)

JFK’s presidency ended suddenly when an assassin killed him in 1963, creating chaos and preventing him from pursuing his primarily progressive political plans.

(Shortform note: Some historians argue that JFK’s assassination had at least one positive consequence—the advancement of civil rights. They suggest that the public and Lyndon B. Johnson, JFK’s successor, both sought to protect JFK’s legacy as a way of mourning his death. This included protecting and eventually expanding JFK’s initial push for civil rights during the rest of the 1960s.)

The 37th President: Richard Nixon

Six years after JFK’s death, Richard Nixon became president during the height of the Vietnam War, a moment of uncertainty for the country and its role in the Cold War. But while Nixon focused on international affairs, problems at home piled up and threatened to undo him. O’Reilly and Dugard explore the complex web of Nixon’s political achievements, failures, and personality.

Personal Life

Nixon was born poor in Orange County, California, and spent much of his youth working to support his family. An excellent student, he was invited to Harvard, but chose the smaller Whittier College so he could stay in California and continue helping his parents. Nixon served in the Navy during World War II and pursued a political career shortly after, quickly rising from Congress to the vice presidency on the strength of his strong anti-communist messaging. After narrowly losing the 1960 presidential election to JFK, Nixon bided his time and gathered a coalition of conservative allies. This strategy paid off with a close election victory in 1968.

O’Reilly and Dugard acknowledge that Nixon had a reputation as a ruthless and ambitious man who had little empathy for others. But they also note that the people close to him spoke often of his intelligence, his sense of humor, and his patriotism.

(Shortform note: Nixon was the first and only American president to be a native of the West Coast, having been born and raised in Orange County, California. (President Ronald Reagan served as governor of California, but was originally a native of Illinois.) Many historians consider Orange County to also be the birthplace of a new kind of American conservatism—an alliance of evangelical Christians, small business owners, and hardline anti-communists. This group empowered and was eventually led by Nixon himself, moving the Republican Party away from its moderate, liberal politics of the past toward a new vision.)

Presidency

Nixon largely focused on international affairs while in office, managing—and after much delay, ending—the Vietnam War while also negotiating a thaw in relations between the US and communist China. But his presidency fell apart starting in 1972 due to the Watergate scandal, when burglars broke into and bugged the Democratic National Committee offices in Watergate, a complex of buildings in Washington, DC. Nixon denied any involvement in the Watergate scandal, and O’Reilly and Dugard suggest that while he likely didn’t know about the break-in ahead of time, he did attempt to cover it up when he learned that the burglars were connected to his political campaign committee.

The media gradually uncovered not only Nixon’s cover-up attempts but also his covert funding of other acts of political spying and sabotage. Over the course of a year, Nixon went from being the landslide victor of the 1972 presidential election to a broadly hated figure. Facing possible impeachment, Nixon chose to resign in 1974. O’Reilly and Dugard explain that Nixon left behind a legacy strongly associated with lying, cheating, and corruption in the public consciousness.

(Shortform note: Despite mounting public anger against Nixon over the Watergate scandal, he was never actually prosecuted—instead, his successor Gerald Ford pre-emptively pardoned him of any crimes he’d committed. This remains a controversial move, with some suggesting that Ford wanted to cover up the full extent of government corruption at the time. Others argue that Ford issued his pardon so both the country and the government could make a clean break from the scandal and move on to better things.)

Part 5: The 21st Century

With the end of the Cold War and the rise of the internet, the 21st-century political landscape changed drastically in only a few short years. Part 5 of our guide will cover both of the 21st-century presidents who’d served their full terms by the time Confronting the Presidents was written: George W. Bush and Barack Obama.

The 43rd President: George W. Bush

George W. Bush became president during a time of peace and prosperity for the US. The Cold War was over, there was no major threat to liberal democracy in the world, and the economy was running smoothly. But all of that was soon to change. O’Reilly and Dugard explore the major twists and turns in Bush’s presidency as well as his background.

Personal Life

George W. Bush was born into a wealthy and powerful political dynasty. The son of George H. W. Bush, who served as president from 1989 to 1993, the younger Bush received a prestigious education at Yale University. Then, he served in the Texas Air National Guard to avoid getting drafted into Vietnam, and he entered politics a few years later. Bush went from a position in Congress to governor of Texas and then to president after a hotly contested election decided by the US Supreme Court in 2000.

O’Reilly and Dugard note that Bush was rumored to be a reckless young man who’d had difficulties with heavy drinking in his past. However, Bush quit alcohol entirely when he was 40 after receiving an ultimatum from his wife. O’Reilly and Dugard describe Bush as energetic and restless, and they emphasize the politeness and dignity he expressed even during the most intense moments of his presidency.

(Shortform note: In addition to his struggles with alcohol, Bush had a complicated relationship with his father. While the two always loved and supported each other, the younger Bush worried about being in his father’s shadow as he followed in his footsteps. He and his father also recognized that the public would always compare them to each other—something that fuelled a bit of a rivalry between the two. This, plus Bush’s recklessness as a young man, created occasional tension between father and son.)

Presidency

O’Reilly and Dugard argue that the Sept. 11 terrorist attacks defined Bush’s presidency, turning him from a controversial president to the leader of a temporarily united country. Bush acted decisively after the attacks. Within weeks, he ordered the invasion of Afghanistan in search of Osama Bin Laden, one of the main figures behind them. He described the invasion as part of a larger war on terrorism, both at home and abroad. O’Reilly and Dugard acknowledge that some of Bush’s measures to fight the War on Terror were controversial, like his use of mass surveillance and torture. But they argue he effectively improved national security.

In 2003, Bush set his sights on Iraq and its dictator, Saddam Hussein. Saddam wasn’t closely affiliated with Bin Laden or his associates; regardless, Bush decided to invade Iraq after a number of reports came out suggesting Saddam possessed nuclear, chemical, and biological weapons. The US deposed Saddam in less than a month, but found no evidence of the weapons of mass destruction described in previous intelligence.

(Shortform note: Bush’s decision to invade Iraq is likely the most controversial of his presidency, and historians continue to debate the factors that went into it. Some point to Saddam’s alleged assassination attempt against Bush’s father in 1991 as a motive, suggesting Bush wanted revenge. Others suggest Bush was continuing his father’s project, since George H. W. Bush invaded Iraq a decade earlier. Still others argue that Bush used Sept. 11 as an excuse to invade Iraq, something he’d already wanted to do anyway.)

The 44th President: Barack Obama

Barack Obama became president as the war on terror was cooling off—and as the 2008 financial crisis was causing economic chaos. O’Reilly and Dugard explore both who Obama was and how he managed these evolving challenges.

Personal Life

Barack Obama was born in 1961 to Ann Dunham, an American academic, and Barack Obama Sr., a Kenyan government official. Both were students at the time, and their relationship didn’t last. Obama was primarily raised by his grandparents in Hawaii. He was an excellent student, attending Harvard Law School. From there, Obama went to Chicago to work as a lawyer and activist—a path that led him to political office. O’Reilly and Dugard explain that as a senator, Obama avoided taking controversial stances. Instead, he focused on planning for a presidential run two years after joining the Senate and became the first African-American president.

(Shortform note: Some argue that Obama’s father provides context for some of the president’s political beliefs. Though he was a bureaucrat later in life, as a young man Obama Sr. was a socialist who may have participated in Kenya’s anti-colonial struggle against the British. Analysts suggest that Obama Sr.’s left-wing sympathies and negative experiences with colonialism—he was imprisoned in a British colonial prison for six months—could have passed down to his son and pushed him further to the left politically.)

O’Reilly and Dugard describe Obama as a serious and disciplined man. They explain that he often made big, ambitious plans in and out of office. He faced a great deal of criticism during his political career, including doubts about his American citizenship—doubts that O’Reilly and Dugard argue are unfounded.

(Shortform note: The doubts about Obama’s citizenship connect to a theory that the former president was born in Kenya, not the United States. The origin of this “birther” theory isn’t exactly clear—it may have begun with a misprint from Obama’s literary agent incorrectly stating his birthplace, or with frustrated supporters of Hillary Clinton when Obama pulled ahead in the 2008 Democratic presidential primary. However, the birther theory took hold most strongly among the conservative Tea Party movement in the 2010s, often connected to other theories about Obama secretly being Muslim or Arab.)

Presidency

O’Reilly and Dugard largely tell the story of Obama’s presidency through two of his major political projects, neither of which completely succeeded or failed: Obamacare and ending the war in Iraq that his predecessor, Bush, had started as part of the War on Terror.

Obamacare, officially known as the Affordable Care Act, was Obama’s landmark piece of legislation to expand the government’s role in providing healthcare. O’Reilly and Dugard argue that while Obamacare did provide many low-income Americans with health insurance, critics viewed it as government overreach. The authors suggest this backlash cost Obama both the House and Senate in the 2010 midterm elections, halting a lot of his political momentum, and that it contributed to increased political polarization throughout the 2010s.

(Shortform note: For context, let’s cover what the Affordable Care Act consists of. The bill has three major parts: First, it places new restrictions on private insurance providers, generally requiring them to expand their coverage. Second, it requires all Americans to have health insurance or else pay a fee. Third, it expands eligibility for Medicaid—state health insurance. The Affordable Care Act has remained largely intact since its passage in 2010 despite over 50 attempts to repeal it, an ongoing effort.)

Obama also wanted to withdraw all American soldiers from Iraq, preferring to fight the War on Terror with smaller tactical strikes and raids like the one that killed Sept. 11 architect Osama Bin Laden in 2011. However, a civil war in Iraq’s neighbor Syria, as well as the rise of terrorism in the region controlled by the Islamic State (ISIS), led Obama to redeploy troops to both Iraq and Syria.

(Shortform note: Many of the conflicts that defined the beginning of the War on Terror—the US invasions of Iraq and Afghanistan, the Syrian Civil War, and the rise of ISIS—have ended as of the 2020s. But the US maintains some degree of military presence in Afghanistan, Iraq, Somalia, and Syria, whether in the form of military bases, military advisors, or drone strikes on terrorist targets. Furthermore, the mid-2020s have seen an uptick in violence in the Middle East with US ally Israel waging war against a number of terrorist groups and launching military strikes against multiple countries in the region.)