Which US President was the greatest military leader?

There’s a lot of debate over which President has the most impressive military background, and history provides no clear winner.  That doesn’t matter though, because today, YOU decide. We’ve rounded up some of the best and brightest Commanders-in-Chief in American history, and want your feedback on their stories of war, heroism, and military ingenuity. Read through the list, pick your favorite, and cast your vote! The favorite might surprise you.

1. Teddy Roosevelt

Teddy Roosevelt

Photo: archives.gov

Teddy Roosevelt didn’t do anything halfway, especially when it came to military strategy. When war broke out in Cuba in 1898, he ditched his post as assistant secretary of the Navy under President William McKinley to form his own volunteer Calvary regiment, the Rough Riders. It was basically a club of badass cowboys, college athletes and lumberjacks who were used to tearing it up on horseback — only now they did it for America, which was even cooler. Once Teddy rounded everyone up, they headed to Cuba, where they would forever leave their mark in the Spanish-American War at the Battle of San Juan Hill.

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Teddy Roosevelt poses with the Rough Riders Photo: Wiki Commons

With only 500 Spanish villagers left standing to protect the town, the nearly 8,000 American troops at the battle thought it was just about over. They soon discovered, however, that higher ground gave their enemies a distinct advantage, and Teddy ordered his Rough Riders up the slope — despite the fact that the men were now on foot and hundreds had already fallen. 

Teddy’s men successfully charged and captured both Kettle and San Juan Hill, leading to the Spanish defeat and ultimate surrender just a few weeks later. His military valor and infectious tenacity both at the front lines and behind the podium would later ignite a huge political following, and make him one of the greatest leaders of the United Sates.

2. John F. Kennedy

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A young JFK in his Navy uniform Photo: Wiki Commons

When most people think of JFK, his military service in World War II tends to take a back seat to the more colorful aspects of his personality and presidency. And while anecdotes about his charisma, good looks and alleged affair with Marilyn Monroe make for great cocktail party banter, one of the most interesting segments of Kennedy’s life happened long before Camelot.

In 1941, the 24-year-old Kennedy volunteered to serve in the Navy. He would soon become a Lieutenant, Junior Grade, and command the Patrol Torpedo Craft (PT) USS PT 109, attacking the Japanese shipping boats dubbed “The Tokyo Express.” The Tokyo Express supplied Japanese forces that were based throughout the island network of the Pacific, and it was the duty of the small PT boats to cut them off before they could reach their destination, as well as aid the U.S. Army and Marine Corps for onshore attacks.

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JFK in the Solomon Islands, 1943 Photo: shmoop.com

The work was hard, but nothing extraordinary — until disaster struck on August 2, 1943. Kennedy had the PT 109 running silent, hoping to go unnoticed by the Japanese, when the watercraft was blindsided by the Amagiri, a Japanese destroyer running perpendicular to the boat at 40 knots. The large warship ripped Kennedy’s boat in half, gutting the watercraft and sending the entire crew into the ocean. One of the surviving men, engineer Patrick Mahone, was badly injured by fuel that had exploded below decks, and Kennedy towed him through the water to a small island that was four miles away, gripping his life vest to keep his head above water. When the eleven survivors finally collapsed on the sand, they had been in the ocean for nearly fifteen hours. 

PT 109 Navy Painting

An artists’s interpretation of what happened to PT-109 Photo: jfklibrary.org

If that’s not impressive enough, JFK got his men off the island by carving a message into a coconut and giving it to two natives, who then delivered it to the PT base at Rendova, ensuring the rescue of Kennedy and his crew.

The men were rescued on August 8th, four days after their boat was destroyed. JFK would later encase the coconut shell in wood and plastic and use it as a paperweight for his documents in the Oval Office. How is this not a movie yet?

3. Andrew Jackson

Jackson-Portrait

Photo: Wiki Commons

Andrew Jackson is one of the more, if not the most, notorious presidents the United States has ever had. His bombastic personality and deeply controversial decision to move Native American tribes to reservations has left many people skeptical — if not deeply disapproving — of his contributions as Commander- in-Chief.

Before he stepped foot in the White House, however, Jackson was making waves in a different way. When he was only 13 years-old, Jackson’s mother was killed during the British invasion of South Carolina in 1788, and Jackson and his brother were taken prisoner by nearby troops. When ordered to shine an officer’s boots, Jackson refused, causing the officer to slash the side of his face with his sword. His brother would later fall ill and die while they were still in confinement, leaving Jackson alone. The event would leave physical and psychological scars that lasted into Jackson’s adult life, and likely forged the defiant, fearless personality that would bring him military success.

Jackson served as a major general in the War of 1812, leading U.S. forces against the Creek Indians, who were British allies at the time. After a five-month assault against the natives, Jackson secured the U.S. an overwhelming victory at the Battle of Horseshoe Bend. The best-known example of Jackson’s military valor, however, was not even technically part of the War of 1812 under which it was fought. The Battle of New Orleans occurred after the close of the war, but before the Treaty of Ghent — an agreement signed by British and American representatives that effectively ended the war — had reached Washington.

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Andrew Jackson defeats New Orleans Photo: history.com

Jackson and a rag-tag band of slaves, frontiersman, militia fighters and pirates took down a full-frontal assault from British forces, despite inferior numbers, training and supplies. News of the impossible victory took the nation by storm, and people were so enamored with Jackson’s military prowess that they didn’t really care when word got out that the entire battle was essentially pointless.

The battle wasn’t entirely devoid of merit, however. The victory helped bar British forces from invading the American frontier, and would later lead to Jackson’s invasion of the Florida territory, which was under Spanish rule at the time. Jackson managed to conquer both St. Mark’s and Pensacola, ensuring the American Acquisition of Florida later in 1821.

Other interesting points of Jackson’s military history: He was the first and only President to be a former prisoner of war, and is estimated by many historians to have competed in nearly 100 duels. Old Hickory was no pushover.  In one duel against Charles Dickinson, a local horse breeder who had insulted Jackson’s wife in the National Review, Dickinson shot Jackson square in the chest, at which point Jackson shot back, shooting his opponent dead. He carried the bullet in his chest for the rest of his life.

4.  George Washington

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Photo: Wiki Commons

George Washington is a figure that completely encompasses American identity, and is treated by many as a kind of national demi-god. Politicians, historians and school teachers around the nation continue to sing the praises of the father of the United States, but it’s easy to forget what this guy actually did among all the patriotic white noise.

One of the first aspects of his life that tends to fall by the wayside is his military achievements. Young Washington’s first taste of war came in 1752, when he joined the British military at twenty years old to fight for control of the upper Ohio Valley during the French and Indian War. Before he became a soldier he had trained as a land surveyor, and his superiors were quick to have him lead expeditions in and around Virginia, the state he grew up in.

During one expedition under British Gen. Braddock, the French and their Native American allies ambushed Washington and the rest of the troops. Braddock was killed almost immediately, and Washington promptly took over, leading the surviving soldiers in a carefully executed retreat. The governor of Virginia would later raise Washington’s rank to colonel to reward him for his military valor, and he was tasked with protecting much of the western frontier.

Washington_Crossing_the_Delaware_by_Emanuel_Leutze,_MMA-NYC,_1851

Photo: Wiki Commons

During his service under the British militia, Washington’s view of the colonies’ mother nation soured. He felt that the British military commanders had little understanding of colonial life and were rude and dismissive towards colonial leaders. This seed would later grow into Washington’s full-on rebellion against British rule, when he formed the Continental Army in June of 1775 and was elected commander-in-chief.

Washington immediately set about forming a navy, creating policies on how to interact with Loyalists, and leading campaigns to gain allies both on the home-front and abroad. The most impressive military moment of Washington’s time as general, however, was arguably the crossing of the Delaware.Washington and his men had hunkered down in Brooklyn Heights, anticipating a British attack on New York City. Gen. Sir William Howe, the British commander of the navy, had other plans. Howe drove Washington’s army out of Long Island and captured the majority of the colonial army, claiming New York City.

Despite this defeat and the colossal British military force — a whopping 34,000 redcoats to a measly 2,400 American soldiers —  Washington didn’t give up.

Instead, in the early, freezing hours of December 26, 1776, Washington and his surviving men crossed over the Delaware River, initiating a surprise attack on Hessian soldiers gathered in Trenton, New Jersey. They would ultimately capture 900 men, later prompting British forces to abandon New Jersey. This embarrassing display of British defeat was a huge source of hope and pride for the American colonists. Washington had many military victories big and small during the Revolutionary War, but his military prowess in New York invigorated an entire people, giving the patriot cause the fuel that it needed to continue to fight —  and win — the war for America.

5. Ulysses S. Grant

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Photo: dailyfinance.com

Though many historians and war buffs contest that Robert E. Lee was one of the greatest American generals of history — and certainly the greater of the two military leaders of the American Civil War — President Ulysses S. Grant made incredible gains for the United States.

Before he became a Civil War hero, Grant graduated from West Point in 1843 and fought in the Mexican War under Gen. Zachary Taylor, where he would gain valuable military experience and be praised for his combat skills and bravery on the battlefield. During this time however, Grant began to fall into a depression. Without the anchor of his wife, Julia, and their young family, he felt alone and aimless. He would eventually turn to alcohol as a means of easing his distress, before retiring to civilian life in 1854 in an attempt to regain control of his life.

When Lincoln called for 75,000 volunteers at the start of the Civil War, however, Grant rushed back to the battlefield.  He began as the colonel of a regiment in Illinois before being promoted to Brigadier General. Then, after  his success in the Western Theater in 1863, he was granted command of all Union armies in 1864. From there, Grant’s star would rise to immeasurable heights.

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Photo: history.com

Grant was also referred to as “Unconditional Surrender Grant,” a nod to his demands at Fort Donelson and Fort Henry, two crucial Confederate posts that he captured. Some felt that his military strategy and trademark terms of surrender were too brutal, but Lincoln stood behind him, reportedly stating, “I cannot spare this man, he fights.”

It was under Grant’s leadership that Gen. William T. Sherman wreaked havoc on Georgia, burning his way through the South during his March to the Sea, also known as the Savannah campaign. Grant himself would fight against Lee and the Confederate forces at Spotsylvania Court House, Cold Harbor and Petersburg, instigating brutal slaughter on both sides of the battle but ultimately weakening the rebel army. Lee Finally broke under Grant’s relentless attacks at the battle of Richmond, where he would flee and then later surrender at Appomattox, securing Grant’s victory and his place in the American Military’s Hall of Fame.

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