These Are the Presidents Who Took the Biggest Risks (and How Donald Trump Compares)

Many critics call President Donald Trump a big risk for both domestic and foreign interests, but how does he stack up against his predecessors? At least one former president, Franklin Delano Roosevelt, saw risks as positive. He called risk, “Bold, persistent experimentation” and did a lot of it. Let’s compare our former presidents’ riskiest moves, including Trump (page 10).

1. Barack Obama taking out Osama bin Laden

Barack Obama speaking in a dark suit against a dark background

Barack Obama took foreign policy risks. | Alex Wong/Getty Images

Obama took a lot of foreign policy risks during his two terms. His biggest may have come when he authorized a Navy SEAL raid to capture or kill Osama bin Laden in Pakistan. The president authorized the move against the advice of Vice President Joe Biden and then-Secretary of Defense Robert Gates. If that operation went wrong, it could have torpedoed his presidency.

Next: This war also came as a calculated gamble.

2. George W. Bush and the war in Iraq

US President George W. Bush speaks

He took risks in defending the U.S. | Jim Watson/AFP/Getty Images

The Sept. 11 attacks transformed Bush from a peace president to a wartime leader who made it his top priority to defend America against insurgent terrorism. ”He is not afraid of risk and he is confident obviously in what he believes, and it has kind of shaped his political career,” said White House communications director Dan Bartlett.

Invading Iraq and Afghanistan kicked off a war that the country still fights to this day. It also later revealed some questionable motives. In retrospect, it fell right in line with the president’s risky reputation.

Next: This president entered a war without Congressional approval.

3. Harry S. Truman and Korea

Harry S Truman

He engaged in Korea. | Keystone/Getty Images

Truman’s response to the Soviet threat included the decision to engage in a conflict with Korea without a Congressional declaration of war. Truman described the deployment as police action taken in conjunction with the United Nations, sidestepping Congress. But that risk had its blowback — after the Korean War reached a stalemate, his approval ratings plummeted.

Next: This president’s response to Soviet aggression could have really backfired.

4. John F. Kennedy and the Bay of Pigs

John Fitzgerald Kennedy

He invaded Cuba. | AFP/Stringer/Getty Images

Even though JFK did not have full confidence he could bring down Fidel Castro’s regime, he invaded Cuba at the Bay of Pigs in 1961. He feared that Castro represented an advance wave of a Communist assault on democracy. He also thought that if he did not invade, it would make him look politically weak.

Subsequently, Kennedy also initiated a marine “quarantine” of Cuba. U.S. ships would intercept vessels suspected of delivering weapons. That created a tense atmosphere and fear of nuclear retaliation. After 13 days, the Soviets agreed to remove their missiles from Cuba. In exchange, the U.S. agreed to respect the sovereign island. That risk could have literally blown up in JFK’s face.

Next: The following president also committed to war without backing.

5. Lyndon Johnson’s Vietnam decision

American President Lyndon Baines Johnson addresses the nation on his first thanksgiving day television programme

He bombed North Vietnam. | Keystone/Getty Images

Johnson initiated a bombing campaign against North Vietnam in March 1965 and then committed 100,000 U.S. troops. All of that without ever consulting Congress or even taking the temperature of the country.  In addition, when he sent an additional 120,000 troops, he did so monthly, to make it seem less extreme.

Subsequently, the war turned into a long-term battle that cost thousands of U.S. lives. It also permanently damaged the country’s confidence in Johnson as a leader. Some risks, it turns out, could have used more forethought.

Next: This president’s risk also led to his losing the office.

6. Richard Nixon and Watergate

Richard Nixon

Watergate was a risk that backfired. | Keystone Features/Stringer/Getty Images

Although Nixon made other impacts during his time in office, the Watergate scandal destroyed his presidency. But that actually does not even register as his biggest risk. During his 1968 presidential campaign, he secretly advised South Vietnamese President Nguyen Van Thieu to resist peace overtures until after the U.S. election. He hoped to get a better deal, once elected.

Those negotiations violated the Logan Act, which forbids private citizens from interfering in official affairs. Nixon’s actions also showed he believed that a president could conduct foreign affairs without Congressional, media, or public knowledge.

Next: This legendarily stoic president took an unconventional approach, as well.

7. Abraham Lincoln and his team of adversaries

President Abraham Lincoln

He worked with rivals. | Alexander Gardner/U.S. Library of Congress via Getty Images

Lincoln famously appointed a “team of rivals,” to work with him because he valued differing opinions. As Donald Phillips points out in Lincoln on Leadership, the president’s constant and regular attention to hearing them eventually worked in his benefit.

Phillips describes how Lincoln also practiced the technique of “management by walking around.” He dropped in on Cabinet officials without warning, visited the troops and his generals, and talked with his citizens. That calculated risk left him open to direct and damaging criticism, but it also made him more approachable. In 1861, he spent more time out of the White House than in it. His personal secretaries reported that he spent 75% of his time meeting with people.

Next: The following president went against his word, and changed the world.

8. Woodrow Wilson and entering World War I

Woodrow Wilson

He entered the war. | Topical Press Agency/Getty Images

Despite running for re-election on his promise not to go to war, Wilson did just that during WWI. That risk basically launched a new chapter in U.S. foreign policy. The resulting League of Nations ended up having no real power, and it did not stop World War II.

However, it did show that European affairs can have a strong effect on the U.S. It also introduced the idea that world powers all influence each other. That led to the creation of the United Nations. We could say Wilson’s risk, while it had its downsides, eventually paid off.

Next: This legendary risk-taker also revolutionized the presidency.

9. Franklin D. Roosevelt’s New Deal

Franklin Delano Roosevelt

He took risks to fix the economy. | Keystone Features/Stringer/Getty Images

Roosevelt not only ran for president during the Great Depression, but instituted the New Deal to fix the economy. His first action as president involved closing all banks, after Black Tuesday. When banks lost people’s money, he shut them down to keep it safe. During his first 100 days, he also proposed the New Deal, and many of its programs still exist today.

He also served as commander-in-chief when the surprise Pearl Harbor Attack took place. During the ensuing World War II, Roosevelt asked congress to enact laws that allowed the U.S. to sell military equipment. He additionally directed the making of atomic bombs. For all of these reasons, he may rank as our riskiest president ever.

Next: So how does Donald Trump compare?

10. Trump takes many risks — and not all of them are calculated

US President Donald Trump waves

He’s unpredictable. | Saul Loeb/AFP/Getty Images

The 45th president seems poised to give all of these a run for their money, with a bombastic style and unpredictable policy. His meeting with North Korea’s Kim Jong Un has many world leaders nervous, as does his consistent baiting. He seems to act without thinking and uses Twitter to speak his mind without reserve.

Trump also alienates other world leaders with his lack of propriety and disregard for convention. All of these add up to an unpredictable leader who takes risks just for the heck of it. But does that make him the riskiest of all? For that, only time will tell.

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