Black Jack in Cuba: General John J. Pershing’s Experience in the Spanish-American War

by Kevin Hymel

To most Americans, San Juan Hill conjures up images of Teddy Roosevelt and his Rough Riders dashing up the hill to victory, but other soldiers also played an important role in driving the Spanish off the heights overlooking Santiago, Cuba. One such soldier was 1st Lieutenant John J. Pershing, the quartermaster of the 10th U.S. Cavalry, the famed “Buffalo Soldiers.” Pershing’s experiences in Cuba gave him important battlefield experience and showed him how an army at war behaves. This would pay off when Pershing led the United States Army into battle on the fields of France in World War I, less than twenty years later.

As tensions heated up between the United States and Spain, Pershing was teaching tactics at West Point. Desperate to join the action he foresaw as inevitable, he bombarded the Assistant Secretary of War, John Meiklejohn, with letters. Realizing the importance of combat duty, he wrote, “if I should accept any duty which would keep me from field service, indeed if I did not make every effort to obtain an opportunity for field service I should never forgive myself.”

Pershing was not totally unprepared for battle. An 1886 graduate of West Point, he had seen duty against the Plains Indians with both the 6th and 10th Cavalry Regiments. The 10th was one of two black cavalry regiments commanded by white officers. Pershing was called “Black Jack” in reference to his service with the 10th, and the nickname stuck long after he left it. He later taught military tactics and mathematics at the University of Nebraska, where he also earned a law degree.

Unfortunately for Pershing, when the battleship Maine exploded in Havana Harbor on February 15, 1898, the Secretary of War froze all West Point instructors to their jobs for the duration of the war. Undaunted, Pershing realized the only way into combat was to be requested for duty by a line unit. He wrote to Col. Guy V. Henry, the commander of his old unit, the 10th Cavalry, requesting to rejoin the unit as regimental quartermaster. Henry sent a letter to Assistant Secretary of War Meiklejohn and Pershing soon showed up at Meiklejohn’s office to press for approval. When Pershing told Meiklejohn “I shall resign and join some National Guard or volunteer unit that stands a chance of being sent to Cuba,” Meiklejohn relented and approved orders for Pershing to rejoin the 10th.

Pershing found his unit in training at Chickamauga, Tennessee and moved with it to Port Tampa, Florida, where it would sail for Cuba. The 10th was part of Brigadier General William R. Shafter’s Fifth Corps, whose mission was to capture Santiago, the Spanish capital of Cuba. Shafter, a veteran of the Civil War and Indian fighting, had grown soft and fat in his sixty-three years and was overwhelmed by the task of preparing his force. Confusion reigned in Port Tampa where thousands of regular Army and volunteer soldiers prepared to leave with little semblance of order. The 10th Cavalry drew space on the Leona, a coastal merchant ship pressed into military service. Loading the ship was conducted without incident and the Leona set sail with 37 other transports on 13 June 1898.

The trip went badly. In addition to the Leona becoming separated from its convoy, the men below decks became seasick and hungry. Their woolen army uniforms were ill suited for the tropic climate, much less existence in a hot, cramped ship’s hold, and there were no cooking facilities aboard ship. Unpalatable field rations were the only food available.

Finally, on 22 June, the 10th Cavalry disembarked at Daiquiri, thirteen miles east of Santiago. There were no port facilities and small boats were used to move the men as close to shore as possible. Many men had to jump from the boats carrying their equipment and wade to shore. Two men drowned during the transfer. The next day, while Pershing stayed on board to supervise the landing, squadrons of the 10th and 1st Cavalry, and two from the 1st Volunteer Cavalry (Rough Riders), clashed with Spanish units at La Guarina then drove the Spanish from their defenses inflicting heavy casualties. The 10th lost one man killed and ten wounded.

The 9th and 10th Cavalry at the battle of La Guarina, supporting the 1st Volunteer Cavalry (Rough Riders).  (Library of Congress)
The 9th and 10th Cavalry at the battle of La Guarina, supporting the 1st Volunteer Cavalry (Rough Riders). (Library of Congress)

Pershing longed to be with his men, but the Leona was ordered west to pick up 1,000 ragged Cuban rebels of General Calixto Garcia’s command who had been fighting the Spanish. Pershing was not impressed with the insurgent fighters: “A miserable lot they are, in my opinion they will prove of little service to the Americans.”

The next day, leading a pack mule laden with supplies, Pershing caught up with his encamped regiment. To his chagrin, he found that the men had earlier thrown away all but their most essential gear and they were now hungry and without shelter. He spent the next five days traveling the narrow jungle trails, bringing up supplies, no easy task considering the confusion on the beaches where only the efforts of individual officers had brought “at least the semblance of order.”

The confusion taxed many men’s patience but not Pershing’s. When one officer complained about the supply problem and that “fat old slob” Shafter, Pershing confronted the complainer and scolded “Why did you come to this war if you can’t stand the gaff? War has always been this way . . . That old man you talk about is going to win this campaign. When he does, these things will be forgotten. It’s the objective which counts, not the incidents.”

By 30 June, enough troops had been landed to begin the advance on Santiago. The 10th moved with its division to within two miles of the city where it set up camp on a hill near the town of El Ponzo, waiting for the other divisions to arrange themselves. A half-mile northwest of his position Pershing spied his division’s objectives, “the dark lines of masked entrenchments and the mysterious blockhouses of the hills of San Juan.” Beyond that he could glimpse Santiago’s strong defenses. He knew the task laid out for the Army would not be easy. No fires were allowed that night and pickets went out to watch for the enemy.

With dawn of 1 July came the crash of artillery, first American, followed by Spanish. For forty-five minutes the duel continued with the Americans getting the worst of it. Their black powder guns poured smoke, revealing their positions, while the Spanish guns, using smokeless powder, remained hidden. Near Pershing, a Hotchkiss gun exploded, wounding two troopers. The frightened Cuban insurgents who were with Pershing fled.

As the barrage subsided, the Americans started down the ridge and moved forward along a jungle path. Colonel Ted Baldwin, the 10th’s commander, ordered Pershing to act as a guide for the regiment, making sure it found its objectives and kept an orderly advance. The task was difficult; artillery and rifle fire rained down as the men mixed with elements of the 71st New York Volunteers along clogged roads inadequate for such large numbers. Pershing could do little but sit on his horse and shout orders to the men. To make matters worse, an observation balloon was sent up next to the advancing column, drawing fire and revealing the American route of approach. The Spanish concentrated their fire on the area around the balloon, whose observer told the troops below that the Spanish were firing on them. Pershing considered this information obvious and entirely superfluous.

Pershing, along with three other officers from the brigade, was posted in a streambed where he dismounted to better urge the men forward. Standing in waist high water, he led one squadron after another forward through exploding shells and intense Mauser fire. As he ran back and forth bringing up squadrons, he spotted General Joseph Wheeler, the division commander, and his staff, mounted on their horses in the middle of the Las Guamas Creek. As Pershing saluted, a shell landed between the two men, drenching them both with water. Wheeler returned the salute, wheeled his horse around and left.

Enemy fire intensified and panic ensued as men fell everywhere. Eventually, by continually running back into the jungle, finding lost groups, and guiding them forward, Pershing managed to get the 10th over the creek. During the action he was continually exposed to enemy fire. One officer who appreciated Pershing’s efforts to organize the men under fire commented “the gallant Pershing . . . was as cool as a bowl of cracked ice.”

As the men of the division waited at the edge of a wooded area below the two American objectives, San Juan Hill and Kettle Hill, they began taking more fire. Spanish snipers, in their elevated position, had a clear shot at any cavalryman who stood. Casualties mounted, a half-hour passed and still no orders arrived to attack. Finally, Lieutenant Jules Ord of the 71st N.Y. decided that he had enough. Shirtless, with a bayonet in one hand and a pistol in the other, he yelled to his men “Follow me, we can’t stay here.” Ord’s charge energized the Rough Riders and parts of the 10th to join the attack. Pershing was amazed and proud at what he saw: “Each officer or soldier next in rank took charge of the line or group immediately in his front or rear and halting to fire at each good opportunity, taking reasonable advantage of cover, the entire command moved forward as calmly as though the buzzing of bullets was the humming of bees. White regiments, black regiments, regulars and Rough Riders, representing the young manhood of the North and the South, fought shoulder to shoulder, unmindful of race and color, unmindful of whether commanded by ex-Confederate or not, and mindful of only their common duty as Americans.”

The men waded across the San Juan River and rushed forward, slowed only momentarily by a barbed wire fence, which most chose to climb under. In the confusion the men of the 10th divided themselves between Ord’s 71st N.Y. charging up San Juan Hill and Roosevelt’s Rough Riders attacking Kettle Hill. Pershing found himself with the Rough Riders, running up the exposed slopes of Kettle Hill. It was quickly taken. In the last push to the top he saw the Spanish fleeing their positions and heading for Santiago.

Pershing had a perfect view from Kettle Hill of the on-going fight for San Juan Hill. Realizing how tenuous it was he, and the other men on Kettle Hill, rushed forward to assist. There they struggled against the worst fire Wheeler, a Civil War veteran, had ever seen. Despite the enemy salvos, the men pushed forward, assisted by the timely arrival of a few Gatling guns brought forward for the attack. A battle yell went up along the American line. After a final, brief American artillery barrage, the troops made a final lunge for the top. Ord, with the help of the 10th Cavalry, was the first American to reach San Juan’s summit where he was immediately killed by enemy fire.

The victory was not without its price. Dead and wounded men lay all over the hill. The 10th Cavalry lost half its officers and twenty percent of its men. Pershing came up on a wounded officer who asked him how badly he was hurt. “I don’t know,” Pershing replied, “but we whipped them, didn’t we?” Pershing also was witness to the moral character of his men when he saw a Buffalo Soldier stop at a trench filled with Spanish dead and wounded, gently lift the head of a wounded officer and give him the last drops of water out of his canteen.

Although driven from the heights of San Juan, the Spanish had not surrendered. At 3:00 a.m. their artillery again opened up on the American positions as small arms fire picked up. The men of the 10th manned their posts and waited for the expected counter attack, but none came. By 5:30 a.m. the firing began to slacken. Just before dawn, entrenching equipment and ammunition arrived, but no food for the hungry victors. As the sun rose Spanish snipers began firing at anything that moved. When a sniper bullet wounded the regiment’s adjutant, Colonel Baldwin promoted Pershing into the position. The rest of the day, while both sides traded fire, Pershing delivered messages to the front and ran the regiment in Baldwin’s absence. The conditions for the men were miserable. Some soldiers formed a bucket brigade from the front trenches to a watering hole a mile to the rear. Frontline soldiers tore off their heavy woolen shirts in the hot air, and soldiers who had a simple frying pan and fork became the envy of the regiment.

The fighting continued into the next day, but actions off the battlefield heartened the American soldiers. About 9:00 a.m. on 3 July, men heard sharper, heavier explosions to the south of Santiago. It was the guns of the U.S. Fleet routing the Spanish Navy. Without their navy, the Spanish army could neither flee nor survive. General Shafter sent a message of truce through to Santiago. The Spanish had until 10:00 a.m. on 4 July to surrender before American ground and naval artillery shelled the city.

During the truce, the men of the 10th continued to strengthen their positions. While the men worked, Pershing read to them two messages: one from President McKinley and one from General Nelson Miles, the Commanding General of the Army, commending them. Miles said he would arrive soon with reinforcements. The men exulted in Miles’s promise. Soon after, Cuban refugees from the city, hoping to escape the expected bombardment, began to cross into the American lines. Pershing was moved at what he saw: “It was a pitiful sight; from daylight until dark the miserable procession trooped past. The suffering of the innocent is not the least of the horrors of war.”

The truce was extended. Shafter kept up the pressure on the Spanish while his men advanced their siege trenches and living conditions worsened. The rainy season began, drenching men and filling trenches with water. Even worse, men started coming down with malaria and yellow fever. Pershing was no exception. Soon he was wracked with malarial fever, but this merely slowed him down. Traveling back to a supply depot, Pershing bargained successfully for a wagon that gave him the means to bring his men food, bed rolls, tenting equipment, medical supplies and cooking utensils. Pershing was everywhere obtaining gear. He visited docks, depots and any place he thought he could find some comforts for his men. He made a special effort to bring up personal baggage to frontline officers.

On 10 July, with no Spanish surrender, the truce ended and Santiago came under fire. Soon the return fire from Spanish guns began to fade. Spanish authorities soon realized the situation inside Santiago was hopeless, and on 17 July 1898 the city surrendered. After the surrender ceremonies between Generals Shafter and Jose Toral, the American troops were drawn up in a line along their six miles of trenches to witness the raising of the Stars and Stripes above the governor’s palace in Santiago. At exactly 12:00 noon, a cheer went up from the American lines as artillery boomed a salute. The campaign was over.

Captain John J. Pershing in 1902.
Captain John J. Pershing in 1902.

1LT John Pershing had excelled in his role during the Cuban campaign. He led troops, filled in for fallen officers, braved enemy fire, and kept his men well supplied. Officers who witnessed his actions were quick to praise. Colonel Baldwin, his regimental commander, wrote Pershing: “You did some tall rustling, and if you had not we would have starved . . . I have been through many fights and through the Civil War, but on my own words ‘you were the coolest and bravest man I ever saw under fire in my life’ and carried out your orders to the letter no matter where it called you.” But the greatest praise Pershing received came from the Brigadier General Leonard Wood, newly appointed military governor of Santiago, who wrote Assistant Secretary of War Meiklejohn of Pershing’s accomplishments. The letter was passed to President McKinley who wrote on it: “Appoint to a Major, if there is a vacancy.” During the seven day cruise, Pershing reflected on what he learned. He had found the fighting spirit of American soldiers excellent, even among the volunteers. As long as men were moving forward their confidence rose; sloth and disease set in only when the troops halted. Keeping units together instead of splitting them up also helped maintain esprit de corps. Pershing also realized that weapons had to be upgraded to include smokeless rifles and artillery; and old commanders would have to be replaced with younger, more agile men. The greatest problem facing the Army, however, was supply. If the Army could not keep supplies coming forward it could not succeed in battle. He came to realize that reliance on civilian staff, who lacked the competence needed in wartime, was the Army’s biggest problem. “Good commissary and quartermaster sergeants or clerks would have been infinitely better and more deserving.” Lessons Pershing learned during the Spanish American War were invaluable. He would draw on them two decades later when he led the largest overseas American army into battle on the fields of France.

For more information on John J. Pershing and the Spanish-American War, read Frank Vandever, Black Jack: The Life and Times of John J. Pershing, Frederick Palmer, John J. Pershing, General of the Armies, and Henry V. Cashin, Under Fire With the 10th U.S. Cavalry.