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In 1901 Brigadier General Frederick Funston masterminded a ‘desperate undertaking’ to quash the guerrilla insurrection that flared up after the Spanish-American War.

In the spring of 1901 Frederick Funston, a young and bold brigadier general of volunteers, approached U.S. Army Brig. Gen. Arthur MacArthur Jr., military governor of the recently occupied Philippines, with an audacious plan. The 35-year-old Funston proposed a covert expedition to the interior of Luzon to penetrate the guerrilla hideout of Emilio Aguinaldo, commander of Filipino resistance to the American acquisition of the islands following the Spanish-American War. His plan called for 81 loyal Macabebe scouts on Luzon to disguise themselves as insurgents and escort several U.S. officers—Funston included—posing as their prisoners. The ruse, he proposed, would allow the group to closely approach and capture Aguinaldo. Funston was not new to the conflict the U.S. government referred to as the Philippine Insurrection; indeed, he had received a Medal of Honor two years earlier while leading the 20th Kansas Volunteer Infantry Regiment as a colonel on Luzon. He was certain his plan would succeed, and he worked to convince his skeptical superior.

Though MacArthur considered the proposed expedition “a desperate undertaking” and told the younger officer on parting, “I fear that I shall never see you again,” he approved what Funston called his “stratagem.” Thus on March 6, 1901, the gunboat USS Vicksburg sailed out of Manila Bay with Funston and his “guerrillas” aboard.

Funston was born Sept. 11, 1865, in New Carlisle, Ohio, to Edward H. Funston, a Union lieutenant in the Civil War, and Ann ( the family moved to Kansas, where Edward would serve in both the state Legislature and the U.S. House née Mitchell) Funston. In 1867 of Representatives. Frederick grew into a slight teen with a wandering spirit. In 1884 he failed the admission test to the U.S. Military Academy at West Point, N.Y. He attended the University of Kansas from 1885 to 1888 but did not graduate. Landing a position as a botanical agent for the Department of Agriculture in 1891, Funston undertook expeditions to California’s Death Valley, the Colorado Rockies and Alaska’s Yukon River basin, collecting specimens and filing dispatches to popular magazines about his adventures. His restless nature next led him to reporting gigs and work on the Santa Fe Railroad.

In 1896, inflamed by a speech by Maj. Gen. Daniel Sickles —the Civil War veteran and former U.S. minister to Spain —vilifying Spain for its repression of the Cuban people, Funston joined the Cuban Revolutionary Army. For the next 18 months he served with distinction in combat and ultimately attained the rank of lieutenant colonel. In early 1898 the 5-foot-4-inch, 120-pound expat officer contracted malaria, and his weight dropped to an alarming 90 pounds. Given leave to return stateside, Funston had almost recovered from his illness when the Spanish-American War broke out. Knowing of the young officer’s recent service in Cuba, Governor John W. Leedy promptly appointed him a colonel of the 20th Kansas Volunteer Infantry. But as Funston was training with his men in San Francisco, Spain sued for peace, so the Army instead sent the Kansans to the Philippines to counter a brewing insurgency.

In the wake of Spain’s defeat the Filipino people had welcomed U.S. troops as liberators and had expected Washington would grant the Philippines independence. When the United States instead moved to annex the islands, large segments of the population rebelled. Aguinaldo, the self-proclaimed president of the Philippine Republic who had led the resistance against the Spanish, led the insurgency against the Americans. On Feb. 4, 1899, two days before the U.S. Senate ratified the annexation, hostilities broke out when insurgents exchanged fire with American sentries guarding a bridge in Manila.

Colonel Funston and his unit were soon in the thick of the fighting on Luzon. During the Battle of Calumpit in late April he led a squad across a partially destroyed bridge over the Chico River and then swam the rest of the river under a hailstorm of gunfire to drive out the entrenched guerrillas. Three days later on the Pampanga River he crossed the river by raft, again under heavy fire, knocked out a Maxim gun that was pinning down the Americans and routed the rebels. Funston, who had been wounded in the hand, earned promotion to brigadier general of volunteers and received a Medal of Honor for his actions.

By spring 1900 he was commanding the 4th District, Department of Northern Luzon, where he battled the insurgents by destroying their supplies, developing an effective intelligence network and, when needed, employing even harsher methods. Gradually his tactics reduced the rebels’ strength and transformed the heavy fighting of the insurgency’s early days into a smaller, simmering guerrilla war.

In February 1901 Funston learned of the capture of rebels carrying dispatches from the elusive Aguinaldo. The dispatches were in code, but signatures on the documents appeared to be in the rebel leader’s handwriting. Leading the group of captured insurgents was Cecilio Segismundo, who was persuaded—the nature of the persuasion is unclear—to reveal information that the rebel leader, a few of his officers and a guard of about 50 men were holed up in the mountain stronghold of Palanan. Segismundo also told Funston that scouts carefully watched the trail to the hideout and would immediately inform Aguinaldo of any attempt to approach Palanan. Once deciphered, the captured documents seemed to support Segismundo’s assertions.

Since a direct assault was obviously out of the question, Funston settled on an alternate plan—the “desperate undertaking” he presented to MacArthur. He was taking an awful risk, too, as joining the Macabebes and posing as leaders of the “rebel” group were a handful of actual insurgents, including Segismundo himself, a rebel officer named Hilario Tal Placido and former Spanish secret service officer Lázaro Segovia. A word by any of them would doom the mission.

After procuring insurgent uniforms, captured enemy rifles and sufficient ammunition, the company set off. Eight days after leaving Manila Bay Vicksburg, its lights screened, arrived at Casiguran Bay in rebel-infested northern Luzon, more than 100 miles from Palanan. Funston’s party went ashore in the ship’s boats under cover of darkness, and at 7 the following morning the men began their long approach march. Their arrival had been noticed, and when they entered the town of Casiguran a local band was waiting to welcome the “victorious” native troops. Townspeople gathered to gawk at the “prisoners,” the first Americans many of them had ever seen.

“The whole situation was so ludicrous,” Funston later wrote, “that it was with difficulty we could keep from laughing, despite the peril of our position.”

The group waited in Casiguran for two days to gather food for the trek to Palanan. Meanwhile, the Macabebes were enjoying the attentions of the local people and spreading the group’s cover story—that they had come upon a party of 10 Americans in the mountains and had killed two and wounded three of them. They had captured the remaining five and would present them to Aguinaldo. To pave the way for the expedition, intelligence experts had prepared letters of introduction on captured stationery over the forged signature of a rebel commander named Urbano Lucuna, from whose force the party was supposed to have come. The rebel commandant had these forged letters dispatched ahead to Palanan.

“The rain never ceased pouring,” Funston recalled, “and from the morning we left Casiguran [on March 17], we were drenched to the skin for a week. We waded more than 60 streams, some of them mere brooks, but others so deep and swift that we had to put our hands on each other’s shoulders and go in up to our armpits.”

Before leaving Casiguran, Funston had received word that Aguinaldo had been reinforced with 400 well-armed men. That intelligence was later to prove false, but during the march it hung like another dark cloud over the wet and tired men.

Nine miserable days later, after fighting their way through swamp and jungle, Funston and his “guerrillas” were within 10 miles of Palanan when they encountered an advance party sent out by Aguinaldo. The insurgents led the Macabebes to a beachside trailhead, where stood two crude shelters—one for the prisoners and the other for their guards. It was then Funston learned the story of Aguinaldo’s reinforcements had been rumor. But in a further complication, Aguinaldo had ordered the prisoners held where they were, while the “rebels” were to continue to Palanan. Funston and his men discussed a plan in whispers before falling asleep.

The following morning the Macabebes resumed their march toward Palanan. Meanwhile, by presenting another forged document, the prisoners convinced the rebels the order to hold them had been rescinded, and they set out after the main group, keeping at a distance in case they encountered another advance party. About a mile from Palanan two insurgent officers did intercept the Macabebes and escorted them to the rain-swollen Palanan River within sight of town. On the riverbank was a small canoe-type banca locals had been using to cross the river. Segovia and Tal Placido crossed with a small group and went to meet Aguinaldo while the rest of the Macabebes worked their way across the river.

The insurgents led the two men to Aguinaldo’s house. Entering his second-floor headquarters, they found the rebel chief in the company of seven officers. Just outside Aguinaldo’s 50 personal guards were forming to greet the newly arrived guerrillas. Segovia and Tal Placido faced a half-hour wait under Aguinaldo’s close scrutiny. They passed the time spinning yarns about the capture of their prisoners, for which they received congratulations from the gathered officers. During the conversation Segovia subtly positioned himself by an open window to watch for his men.

When the remainder of the Macabebes finally arrived, they fell in facing Aguinaldo’s guard across a small square. Segovia quickly stepped to the head of an outside stairway and signaled to Gregorio Cadhit, the man leading the Filipino raiders.

“Now is the time, Macabebes!” Cadhit cried out. “Give it to them!” In a nervous state of excitement the men fired a ragged volley, killing two of the rebel guards and wounding a third, before easily subduing the survivors.

Aguinaldo, mistakenly thinking his men were firing in celebration, stepped to the window and berated them for wasting their ammunition. At that moment Tal Placido grabbed Aguinaldo, threw him to the floor and pinned him as several rebel officers moved to draw their weapons. Segovia rushed back into the room, firing his pistol and wounding two of the seven men. One of the wounded and another man surrendered, but five jumped from the windows into the river.

Meanwhile, Funston and his officers, hearing the shots, quickly crossed the river and rushed into the camp. As they arrived, a blood-spattered Segovia informed them Aguinaldo had been captured. Funston then entered the house, introduced himself and his officers to the rebel leader and— in the fluent Spanish he had learned while fighting in Cuba —told him that the recently arrived “guerrillas” were in fact American-allied Filipinos and that he was a prisoner.

“Is this not some joke?” Aguinaldo replied in a daze.

“I assured him that it was not,” Funston recalled, “though, as a matter of fact, it was a pretty bad one on him. While naturally agitated, his bearing was dignified, and in this moment of his fall there was nothing of the craven.”

The American officers tended to the wounded men even as they struggled to reign in “the wildly excited Macabebes.”

Funston had previously arranged that Vicksburg would meet the men in Palanan Bay on March 25 at a spot 8 to 10 miles from the town. The men arrived in Palanan a day early and spent the time resting after their march and eating food left by the since vanished villagers. On the morning of the 25th the group set out for the bay, reaching the beach about noon to the welcome sight of smoke from Vicksburg’s stack.

Picked up by the ship’s boats, Funston’s men and their captives arrived at Vicksburg to repeated cheers from crewmen gathered along its rails. In three days they were back in Manila. A month after his capture Aguinaldo formally admitted defeat and issued a proclamation calling for his followers to lay down their arms. A year later, on July 4, 1902, President Theodore Roosevelt declared the insurrection over and proclaimed a general amnesty. The war had claimed 4,234 American lives with another 2,818 wounded. The insurgents had incurred at least 16,000 casualties, while some 200,000 Filipino civilians had died, mostly from disease and starvation.

News of Funston’s expedition and the capture of Aguinaldo was greeted in America with celebrations almost equaling those that had greeted the news of Commodore George Dewey’s victory over the Span- ish fleet at Manila three years earlier. Funston was promoted to brigadier general of the Regular Army and received a telegram from Roosevelt congratulating him on “the crowning exploit of a career filled with cool courage, iron endurance and gallant daring.” Funston became a national hero.

But in the months that followed some Americans objected to the devious manner in which the capture had been engineered. The Boston Post editorialized that “as the details have come to light, contempt and disgust have taken the place of admiration,” while writer Mark Twain sniped that Funston’s “conscience [had] leaked out through one of his pores when he was little.” Even the London Saturday Review weighed in, calling the capture of Aguinaldo “a gross act of treachery.”

The furor eventually blew over, and Funston continued his Army career. As commander of the Presidio of San Francisco he again courted controversy during the 1906 earthquake and devastating fire. Though his efforts to create firebreaks saved much of the city, he also declared martial law, infamously ordering all looters be shot on sight. Funston was later promoted to major general—the highest rank in the Army at that time—commanded the Mexican border region at the time of Pancho Villa’s raid on Columbus, N.M., directed Brig. Gen. John Pershing’s pursuit of Villa and in 1917 was expected to be named commander of the American Expeditionary Forces then being readied to join in World War I. Before the announcement came, however, on Feb. 19, 1917, Funston collapsed and died of a heart attack in San Antonio, Texas. He was 51. Command of the AEF fell to Pershing.

In later years William Allen White, an American newspaperman and 1923 Pulitzer Prize winner who had known Funston at the University of Kansas, bemoaned the loss of “a man as dashing as Sheridan, as unique and picturesque as the slow-moving, taciturn Grant, as charming as Jackson, as witty as old Billy Sherman, [and] as brave as Paul Jones.”


Chuck Lyons is a retired newspaper editor and freelance writer who has written extensively on historical subjects. He is a frequent contributor to Military History. For further reading Lyons recommends Memories of Two Wars, by Frederick Funston, and Forgotten Heroes, by Susan Ware.

Originally published in the January 2015 issue of Military History. To subscribe, click here.