Top 20 Embarrassing US Presidential Moments

Top 20 Embarrassing U.S. Presidential Moments

Welcome to WatchMojo, and today we’re counting down our picks for the most questionable decisions and politically fraught moments that left permanent smears on the legacies of U.S. presidents.

#20: George W. Bush

Mission Accomplished Speech (2003)

In May 2003, six weeks after invading Iraq, President George W. Bush gave a speech in front of a “Mission Accomplished” banner, declaring the end of “major combat operations” in the country. However, the conflict was far from over. In many ways, it had only just begun. The war went on for eight more years, with the majority of deaths occurring after this speech. When the criticism began pouring in, the Bush administration claimed the banner was requested by the Navy. They then stated that “Mission Accomplished” only referred to the initial invasion, not the war. This incident echoed earlier misinformation by the Bush administration regarding Iraq’s alleged possession of weapons of mass destruction, despite hardly any intelligence supporting such claims.

#19: George Washington

The Whiskey Rebellion (1791-94)

In 1791, just two years into his presidency, George Washington’s administration enacted what became known as the “whiskey tax.” Proposed by Treasury Secretary Alexander Hamilton, its aim was to generate revenue to tackle the national debt incurred during the Revolutionary War. This tax faced staunch opposition from small farmers, who deemed it unfair since they had to distill their grain into whiskey for easier transport and sale. The backlash quickly turned violent, with farmers refusing to pay and even attacking tax collectors. In response, Washington personally led an army to quash the protests, but the rebels all fled and no conflict ensued. While Washington managed to suppress resistance to federal laws, the tax failed to achieve its goal and was repealed in 1802.

#18: Grover Cleveland

Sex Scandal (1884)

During the presidential elections of 1884, Democratic candidate Grover Cleveland was seen as a formidable option, earning voter support for his anti-corruption stance. However, in the lead-up to the election, allegations surfaced that Cleveland had fathered an illegitimate child with a widow named Maria Halpin. Halpin claimed that Cleveland sexually assaulted her, then had her committed to an insane asylum and put their child up for adoption. When the scandal became public, Cleveland admitted to paying Halpin child support. His opponents seized upon the controversy, creating the chant “Ma, Ma, where's my Pa?,” which dogged Cleveland’s campaign. Despite the shocking sex scandal, Cleveland’s supporters remained loyal, helping him secure a narrow victory at the polls.

#17: George H. W. Bush

“No New Taxes” (1988)

By now, voters have grown accustomed to politicians failing to fulfill their campaign promises. But when a candidate centers their campaign around a key issue, they should probably expect to be held accountable. That was precisely the case with President George H. W. Bush. Throughout his 1988 campaign, Bush consistently pledged not to introduce any new taxes if elected. He emphasized this commitment at the Republican National Convention, stating “Read my lips: no new taxes.” Well, guess what, there were in fact several new taxes. Bush’s backtrack on this promise lost him the support of many within his party, and became a focal point of the 1992 election, where Bill Clinton successfully portrayed him as untrustworthy. This ultimately contributed to his re-election defeat.

#16: Thomas Jefferson

The Embargo Act (1807)

During the Napoleonic Wars, America sought to remain neutral, resisting pressure from Britain and France to join the conflict. When the British began forcing U.S. sailors to join their Navy, President Thomas Jefferson decided to sign the Embargo Act of 1807, which halted all American exports abroad. Jefferson hoped that this would pressure Britain and France to respect American neutrality. Instead, this strategy backfired, as the act negatively affected the U.S. economy, leading to widespread smuggling and protests, especially in the New England region. This was particularly damaging for America, which was a relatively new nation at the time. Faced with growing opposition, Jefferson quietly repealed the act in the last days of his presidency.

#15: Woodrow Wilson

The Espionage Act (1917) & Sedition Act (1918)

America’s entry into World War I in April 1917, after nearly three years of neutrality, was met with significant domestic dissent. To suppress this opposition, President Woodrow Wilson signed two laws: the Espionage Act of 1917 and the Sedition Act of 1918. The Espionage Act originally aimed to crack down on actual espionage, by penalizing interference in foreign policy and military operations. However, the Sedition Act greatly expanded its scope, prohibiting disloyal speech against the U.S. government, which seemed to violate the Constitution's free speech protections. These acts resulted in widespread prosecutions, targeting socialists and pacifists, including notable figures like Eugene V. Debs. The Sedition Act was ultimately repealed in 1920, but the Espionage Act remains in effect today.

#14: John Adams

The Alien and Sedition Acts (1798)

Woodrow Wilson wasn’t the only president to suppress dissent against the government. Back in 1798, President John Adams enacted four laws called the Alien and Sedition Acts, amid concerns of an imminent war with France. These acts targeted immigrants and political dissidents, who Adams feared would side with France in the event of war. Among the four laws, three were Alien Acts, which toughened the citizenship process for immigrants and allowed their deportation if deemed dangerous. The fourth, a Sedition Act, punished anyone spreading false and malicious statements about the government. Naturally, these acts faced strong public opposition, sparking protests nationwide. This backlash provided leverage for Adams’ opponent Thomas Jefferson, who successfully capitalized on it and won the presidential election in 1800.

#13: Andrew Johnson

Reconstruction & Impeachment (1865-68)

Abraham Lincoln’s assassination left Andrew Johnson with the task of reintegrating former Confederate states and previously enslaved people into the United States. Johnson’s Reconstruction policies favored leniency towards the rebels, allowing them to easily rejoin the Union and uphold a system that was essentially still slavery. These policies enraged Congress, which passed laws to counter them, kicking off a bitter struggle with the president. In August 1867, Johnson fired Secretary of War Edwin Stanton, in violation of the Tenure of Office Act. The following year, Congress impeached Johnson, making him the first president to face such a resolution. Although he was narrowly acquitted by the Senate, Johnson’s presidency was severely weakened and he failed to win the Democratic nomination in 1868.

#12: James Buchanan

His Entire Presidency (1857-61)

James Buchanan’s single term as president occurred in the mid 19th century. Since then, many successors have come and gone. Yet, several historians still consider him the worst president in U.S. history. This is due to his apparent indifference to the impending Civil War. After his inauguration, Buchanan viewed slavery as an issue of little importance. Instead of trying to lessen the rift between the North and the South, Buchanan believed he shouldn’t interfere in states’ issues. He had pledged not to run for a second term, and during the “lame duck” period between his successor’s election and inauguration, Southern states began to secede. Buchanan essentially crossed his arms and watched them leave; his incompetence inevitably resulting in the Civil War.

#11: Warren G. Harding

The Teapot Dome Scandal (1921-23)

President Warren G. Harding was in office for only two years before his untimely death. But in that little time, he was involved in one of the most shocking political scandals ever. Following his inauguration in 1921, Harding placed his close friends in high-ranking positions, including Albert B. Fall, whom he appointed as Interior Secretary. Harding gave Fall control over three Naval oil fields, whose drilling rights the secretary then leased to private oil companies in exchange for bribes. This shady deal was first reported in April 1922, resulting in a Senate investigation. At the time of his death in August 1923, Harding was beloved among the American public, but as the details of this investigation surfaced, his reputation was effectively tarnished.

#10: Donald Trump

Convicted of Felony Crimes (2024)

Before Donald Trump’s election in 2016, 44 individuals had served as president of the United States. Yet, in 2024, he made history as the first one to be convicted of a crime. The landmark case stemmed from hush money payments Trump made to adult film star Stormy Daniels to keep their alleged sexual encounter under wraps. The prosecution argued that Trump falsified business records to conceal these payments, a felony under New York law. The trial became a media spectacle and concluded with the jury finding Trump guilty on all 34 counts. This case was one of several criminal charges Trump faced, including his alleged involvement in the January 6th insurrection aimed at overturning the 2020 election, which he lost to Joe Biden.

#9: Bill Clinton

The Lewinsky Scandal & Impeachment (1998)

More than a century after Andrew Johnson’s impeachment in 1868, Bill Clinton became the second U.S. president to be impeached by Congress, in 1998. Clinton’s impeachment was related to an extramarital affair he had with White House intern Monica Lewinsky. Lewinsky confided in her colleague Linda Tripp, who secretly recorded their conversations and handed the tapes to an Independent Counsel, which was already investigating Clinton on other matters. The ensuing scandal eventually led to his impeachment by the House of Representatives on charges of perjury and obstruction of justice, as he had lied under oath about the affair. Though Clinton was ultimately acquitted by the Senate, the scandal left a lasting stain on his legacy.

#8: John F. Kennedy

The Bay of Pigs Invasion (1961)

In early 1960, President Dwight Eisenhower approved a CIA plan to overthrow Cuban leader Fidel Castro. That plan was not executed until the following year, after John F. Kennedy took office. On April 17th 1961, over 1,400 Cuban exiles, who had been trained by the U.S., landed at the Bay of Pigs to launch a full-scale invasion. However, their attempt was dead on arrival. The insurgents on the ground were met with unexpected resistance by Castro’s forces and were easily overpowered, especially after Kennedy withheld further air support. Within three days, they had all surrendered. The fiasco became a significant embarrassment for Kennedy, undermining his credibility in the international community and escalating Cold War tensions.

#7: Herbert Hoover

Mexican Repatriation (1929-39)

Shortly after Herbert Hoover took office in 1929, the U.S. stock market crashed, which sparked the Great Depression. Hoover’s strategy to tackle this economic disaster was to blame Mexicans in the U.S., accusing them of taking American jobs. As a result, his administration oversaw the deportation of up to 1.8 million people to Mexico, many of whom were actually U.S. citizens. Known as the Mexican Repatriation, this scheme was carried out through raids, roundups and pressure tactics that forced many individuals to leave voluntarily. Unsurprisingly, this did nothing to ease the Great Depression, which ended up contributing to Hoover’s defeat in the next election. In 2005, the state of California formally apologized for its role in the repatriation.

#6: Lyndon B. Johnson

Escalating the Vietnam War (1964-68)

When Lyndon B. Johnson became president in 1963 following JFK’s assassination, the Vietnam War had already been raging for nearly a decade. At first, American involvement was fairly limited, but this changed dramatically under Johnson. The turning point was the Gulf of Tonkin incident in 1964, where North Vietnamese forces supposedly attacked U.S. Navy ships. Although this attack was later disproven, it led to the Gulf of Tonkin Resolution, which gave Johnson authority to escalate U.S. military actions in Vietnam. By 1967, there were over 500,000 American troops in Vietnam, many of whom lost their lives. Johnson’s escalation of the war became highly unpopular in the U.S., sparking nationwide protests and resulting in his decision not to seek re-election.

#5: Ronald Reagan

Iran-Contra Affair (1985-87)

In 1986, Ronald Reagan and several of his administration officials became embroiled in a notorious political scandal. They had secretly orchestrated the sale of weapons to Iran, which was under an arms embargo, to secure the release of seven American hostages. The profits from this sale were then illegally diverted to fund Contra rebels in Nicaragua, who were fighting the leftist Sandinista government. This was in direct violation of a congressional amendment that banned American aid to the group. When the affair was exposed, it became a major embarrassment for Reagan, raising concerns about his administration’s integrity and oversight. Around the same time, Reagan also faced criticism for his delayed response to the AIDS epidemic, which had already been a significant crisis for years.

#4: Franklin Pierce

The Kansas–Nebraska Act (1854)

Franklin Pierce, a one-term president, is often ranked among the worst and most forgettable leaders in U.S. history. Pierce’s administration is largely remembered for passing the Kansas–Nebraska Act in 1854. This act created the territories of Kansas and Nebraska, and allowed settlers to decide on the legality of slavery through voting. Though it was intended to reduce tensions over slavery, the bill backfired, instead reigniting fierce debates around it. Pro- and anti-slavery settlers rushed to Kansas, hoping to outnumber each other and sway the vote. This led to violent clashes between the two sides, known as “Bleeding Kansas.” Instead of uniting the country, the Kansas–Nebraska Act only deepened divisions, stoking the fires that culminated in the Civil War.

#3: Richard Nixon

The Watergate Scandal & Resignation (1970-74)

Few things are as humiliating for a U.S. president as resigning from office. Richard Nixon was the first to experience this due to his involvement in the Watergate scandal. Nixon was largely popular during his first term, but to ensure his re-election in 1972, his administration and campaign orchestrated the wiretapping of the Democratic Party headquarters. However, the men sent to do the job were caught red-handed and eventually linked to Nixon’s campaign. Desperate to hide his administration’s involvement, Nixon tried to obstruct the investigation. This was revealed by his own taped recordings, leading him to resign rather than face impeachment. Ironically, Nixon had already secured re-election in one of the largest landslides in history, which made the whole fiasco pointless.

#2: Franklin D. Roosevelt

Internment of Japanese Americans (1942-46)

Following Japan’s surprise attack on Pearl Harbor, public opinion in the U.S. slowly began to turn against Japanese Americans. To address fears of further Japanese attacks or sabotage, President Franklin D. Roosevelt issued Executive Order 9066. This order allowed the U.S. government to forcibly remove and relocate people of Japanese descent to internment camps. As a result, about 120,000 Japanese Americans, many of them U.S. citizens, were uprooted from their homes and forced to live under harsh conditions, simply due to baseless fears of espionage. Years later, the Ronald Reagan administration officially apologized to the former detainees for this grave injustice, and paid $20,000 in reparations to each survivor.

#1: Andrew Jackson

The Trail of Tears (1830-50)

In the early 1800s, tensions ran high between Native Americans and white settlers over the ownership of indigenous lands in the South, which were ideal for cotton farming. These settlers found a powerful ally in President Andrew Jackson. In 1830, Jackson signed the Indian Removal Act, authorizing the forceful displacement of indigenous tribes from their ancestral lands. Between 1830 and 1850, about 60,000 Native Americans were removed from their homes and marched over a thousand miles to designated Indian territory across the Mississippi River. Referred to as the “Trail of Tears,” this journey was brutal and left thousands dead from disease, exposure and starvation. Today, many scholars view it as an act of genocide and ethnic cleansing against Native Americans.


Which of these appalling moments left you shaking your head in disbelief? Let us know in the comments below.