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Along the remote windswept coast of southern Texas, two days’ sail from Galveston, lay a backwater, mosquito-infested village called La Vaca. About as far removed from Richmond and the war in the East as one could get and still be within the borders of the Confederacy, La Vaca—later known as Port Lavaca—hardly seemed worth military protection. Still, Captain Daniel Shea’s company of Texas Light Artillery, a small poorly equipped home guard unit consisting mainly of middle-aged men unfit for active field service, kept a determined vigil on Matagorda Bay.

All remained quiet on this western front until one day in the fall of 1862, when a small Union armada brazenly steamed into the bay and fired more than 250 rounds onto La Vaca’s streets and into the homes of the soldiers manning the port’s guns. One of those men, a 6-foot-3 gunsmith originally from Ohio, swore that would be the last time a Northern fleet slipped into a Southern harbor without a fight.

The gunsmith, Private Edgar C. Singer, was no stranger to new contraptions and risky ventures. A nephew of Isaac Merritt Singer, the inventor of the first commercially successful sewing machine, Edgar also had worked on his uncle’s sewing machine design and had been awarded a patent for “Improvements.” It was hardly surprising, then, that within days of the La Vaca attack Private Singer began experimenting with small charges of gunpowder in a water-filled barrel behind his house. He quickly became convinced that the destructive power of gunpowder could be unleashed from an underwater mine. But he needed both men and money.

For men, Singer turned to the local Masonic lodge, which he had joined upon arriving in Texas in 1840. His first recruit and partner in experiments was lodge leader and friend Dr. John Fretwell, a 47-year-old private in Shea’s artillery company. To demonstrate their new nautical weapon in La Vaca, Singer and Fretwell chose an old partially beached hulk as the target.

As one postwar report noted: “The mine was placed alongside and set off, and the vessel was blown to atoms. Commander Shea was astounded and immediately ordered Singer to report to General [John] Magruder at Houston.”

By the time Singer and Fretwell arrived in Houston to meet with Magruder, the general was mobilizing forces for the recapture of Galveston, which had fallen to a Union flotilla in early October. Magruder launched a joint land and sea attack on the port on December 31, 1863, capturing Gal-veston the following day—the first and only time that the Confederates reclaimed a major port city from the Union.

Magruder was skeptical of Singer’s mine contraption, but he eventually gave the inventors 25 pounds of gunpowder and instructed them to demonstrate their device in Buffalo Bayou, the waterway running through Houston. Singer and Fretwell submerged their mine, then floated an old scow above it. A report noted that when the boat struck the mine, “she was blown into kindling wood….”

A highly pleased Magruder ordered Singer to report to Maj. Gen. Dabney H. Maury, commanding the District of the Gulf, with headquarters at Mobile, Ala. Engineers who subsequently evalu­­­ated the merits of Singer’s device for the War Department in Richmond urged its adoption “as a powerful accessory to our limited means.”

Singer went to work fabricating the explosive devices in his small workshop. The torpedo he created consisted of little more than a cylinder-shaped, watertight metal canister of gunpowder with a spring-loaded detonating rod. When a passing vessel triggered the mine, a spring-driven rod slammed into the end of the metal canister and detonated two internal percussion caps. The entire device was chained to a small anchor and submerged about 3 feet beneath the water, with its four-pronged detonating trigger in an upright position.

Although he had limited means, Singer managed to recruit more volunteers to help with torpedo production from his Masonic lodge. The Masons who made up the core of his operation included jeweler James Jones; William Longnecker, the 51-year-old owner of a livery stable; merchants John D. Braman and Robert W. Dunn; C.E. Frary, a Canadian-born carpenter and Singer’s brother-in-law; David Bradbury, a 51-year-old contractor who would be placed in charge of Singer’s torpedo facility at La Vaca and later of all torpedo operations west of the Mississippi; and 37-year-old store owner and father of five B.A. “Gus” Whitney.

In early February 1863, most of Singer’s group traveled to Richmond to demonstrate the new mine to the War Department, and the following month the Confederate Congress approved an act “to provide and organize engineer troops.” Secretary of War James Seddon authorized Singer to form a company of no more than 25 men for a special torpedo service to be attached to the Bureau of Engineers under chief J.F. Gilmer, subject to the immediate orders of the commander of the district in which they were operating. Captain Singer then organized a unit he called “Singer’s Submarine Corps.”

Confederate authorities also furnished the group with the necessary ammunition and materiel for manufacturing the devices, as well as free transportation for both the men and the machines. Compensation for their efforts was to be 50 percent of the value of all vessels of war and other Federal property they were able to destroy. Their devices were to be fully protected by patents.

With those details worked out, Seddon put the group to work immediately, transferring Singer and Robert Dunn to the Engineer Troops and ordering them to report to General Joseph E. Johnston at Morton, Miss. The group also sent operators in Richmond, Charleston, Mobile, Wilmington, N.C., and Savannah, Ga.

While mining the port of Mobile some weeks later, Singer and Fretwell met fellow Masons James McClintock, Baxter Watson and Horace Hunley, three inventors from New Orleans who had built—and lost—two experimental submarines in the past two years. The three were inducted into what was now being called the Singer Secret Service Corps, and the group decided to finance construction of a third submarine for $15,000. From the ranks of this secret organization, five men stepped forward to purchase shares in the project. Singer purchased one-third of the vessel at a cost of $5,000; Hunley retained another third. The remaining shares were evenly divided between Dunn, Braman and Whitney.

Singer and several company members then returned to Richmond, leaving Dunn, Braman, Whitney, McClintock and Watson in Mobile to oversee fabrication of the new submarine and some underwater mines. Late in the spring of 1863, with Confederate fortunes in Mississippi deteriorating rapidly, Fretwell and Hunley were dispatched to Yazoo City, Miss., to persuade Navy Lieutenant Isaac N. Brown to use their torpedoes to mine the water approaches leading to the city’s Confederate shipyards. On July 4, Vicksburg surrendered, and five days later the last Southern stronghold on the Mississippi River fell to Union forces.

Fretwell and his fellow operatives moved quickly to anchor several mines just below Yazoo City. The time had come to prove the military worth of their deadly invention. Within hours after the mines had been placed, Federal gunboats steamed up the Yazoo River. The ironclad Baron DeKalb jarred loose a detonating rod, igniting a mine, and quickly sank to the bottom of the muddy river. A few days later Union Admiral David Dixon Porter described the device that had sunk the ironclad in a report to his superiors in Washington as “some new invention of the enemy.”

Fretwell and Hunley quickly made their way back to Mobile and shared news of DeKalb’s sinking with other Singer members. Singer himself arrived in Mobile a few days later, just in time to witness the long-awaited launching of their group’s submarine. Soon after its successful trial, General John Slaughter sent a message to General P.G.T. Beauregard in Charleston: “July 31, 1863. My Dear General: This will be handed you by Messrs. B. Watson and B.A. Whitney, the inventors of a Submarine boat which they desire to submit to you for examination.…So far as I am able to judge I can see no reason why it should not answer all our sanguine expectations.”

Actually, word of the submarine’s existence had already reached Beauregard by way of Brown, who had recently been transferred to Charleston. Fretwell had briefed Brown about the submarine some weeks earlier. Upon hearing of the secret weapon, Beauregard dispatched a telegram to Mobile: “August 2, 1863. General Maury: Commander Brown C.S.N. informs me Mr. Fretwell has a submarine boat which could be used here successfully. If so please order, with consent of owners, transportation for it and party to work it.” Beauregard didn’t know that Whitney and Watson were already en route to Charleston, hoping to meet him.

The submarine would be christened H.L. Hunley after its most active supporter. Within days the bulk of the Singer group had made arrangements to join in the venture.

In late August the hand-cranked submarine, with its buoyant trailing contact mine, made at least three nocturnal attempts against Federal monitors in the harbor. For an unknown reason, however, the group wouldn’t allow a Confederate naval officer to accompany it on patrols. That decision, combined with the fact their various evening expeditions seemed to accomplish nothing, quickly prompted military authorities to seize the submarine and turn it over to the Confederate Navy.

Singer soon received both good and bad news about his inventions and operations. The bad news was that Gus Whitney, one of the original Hunley investors, had died from pneumonia after serving on the vessel. The good news was that, while attending meetings in Richmond, Singer received a Confederate patent for his mine design. After the military seized Hunley, however, an untested crew of Confederate sailors that had volunteered to man the submarine accidentally sank it next to the Fort Johnson docks, with five of the nine men aboard drowning.

Horace Hunley then brought in another crew, headed by Lieutenant George Dixon, from Mobile. At one point, when Dixon was absent, Hunley tried to captain the submarine, but sank it, killing himself and the crew. Once again Hunley had to be raised from the bottom of Charleston Harbor. Its new crew included Lieutenant Dixon, eight volunteers and engineering officer William Alexander. “It was Winter,” Alexander would write later, “therefore necessary that we go out with the ebb and come in with the flood tide, a fair wind and a dark moon.…On several occasions we came to the surface for air, opened the cover and heard the men in the Federal picket boats talking and singing. During this time we went out on an average of four nights a week.”

As Dixon and his crew continued their patrols, Singer returned with some of his men to Charleston and created several new torpedoes to be used on the sub. Back in Richmond, Singer, Dunn and Braman reached an agreement with the Confederate War Department on the construction of a new ironclad torpedo boat.

About this time, Singer received word that Hunley had sunk the Federal steam sloop of war Housatonic on the night of February 17, 1864—the first time a submarine had sunk an enemy ship. From Richmond to the backwater garrisons scattered along the Texas coast, news that an enemy blockader had been sunk by a Confederate sub provided a much-needed shot in the arm for Southern morale.

That euphoria was tempered by the loss of Hunley, which never returned from the successful mission. Its final resting place remained a mystery until the summer of 1995, when adventure novelist and underwater explorer Clive Cussler discovered the sub’s buried remains several miles outside of Charleston Harbor.

In early March Dunn was instructed to take plans for new ironclads and other vital documents to General Magruder’s Houston headquarters. He traveled from Richmond to Mobile. Then, accompanied by a Colonel Ward and a Colonel Clark, two officers attached to a band of Missouri guerrillas, he attempted to cross the Mississippi under cover of darkness. Dunn later admitted, “In crossing the Mississippi River on the night of the 16th instant…I had the misfortune to loose [sic] my papers, having been closely pursued by launches from a gunboat, and fired at three times from a small swivel gun on their bows, before nearing the shore and twice afterwards.”

More than likely, Dunn threw the papers overboard when he was harassed by the Union launches. That proved fortuitous for the Federals, for among the many documents they found floating in the water was Dunn’s list of Southern operatives, including the names of Singer corps members and the names and locations of nearly 50 Rebel agents and saboteurs operating along the Mississippi. Within days Admiral David Porter, the Mississippi Squadron’s flag officer, issued General Orders No. 184, which in addition to listing those names contained a proviso that captured and identified Singer members would be “shot on the spot.”

Dunn arrived in Houston several days later. Without orders or documents, he penned a letter of introduction to General Magruder that detailed the Singer groups’ activities related to torpedo boats over the past year:

We were…ordered by the Secretary of War, to construct one boat at Selma, Alabama, and one at Wilmington, N.C., of the following dimensions vis. 160 feet long, 28 foot beam and 11 foot hold with flat deck, carrying all their machinery below—to be iron sheathed and with no capacity for guns, and only showing 2 feet above water when ready for work. They is to be arranged with torpedoes, worked from below decks, and through tubes, forward, aft, and on both sides.

It is believed by Engineers of the highest rank, after a full investigation of our plans, that these boats will be perfectly able to raise the Blockade of all the Harbors in the Confederacy. Quite a number of small boats, known as ‘cigar boats,’ for night attacks are now being constructed at Richmond, Wilmington, Charleston and Mobile.

Our success in the use of the stationary Torpedo, has been the destruction of the Enemies Transport Greg Claud in the Atchaffalger Bay, La. [not verified in Federal records], in June last, killing and drowning 140 men; the Gun boat Dekalb, of 13 guns on the Yazoo River in July last destroying her entirely with 180 men; A gunboat in York River (name not recalled) was blown up by one of them, destroying the boat and crew and injuring another Boat badly that lay near by. The sloop of war Housatonic was destroyed in Charleston Harbor, by one of our torpedoes, attached to the prow of [our] small submarine boat, propelled by nine men….These successes show conclusively the certainty of explosion of our torpedoes.

Dunn made a good case for “forcing the enemy’s fleet lying off our bars and harbors, to take some of our medicine” and soon was constructing four small submarines at Shreveport for the defense of the Red River, while two huge ironclad vessels—using torpedoes discharged through tubes as an offensive weapon—would be built for use against the Federal blockading squadron off Galveston.

As Dunn’s negotiations with Magruder continued, Singer and Braman were ordered back to Texas to help with the submarines’ construction. Fretwell left James McClintock and Baxter Watson in charge of the Mobile facility and went north to Richmond to oversee torpedo operations with fellow operative James Jones. Fretwell’s torpedo activities were well known to Robert E. Lee, who revealed in a handwritten document that Fretwell had personally “received my permission to operate on the James River.”

In the weeks that followed, the Singer operatives still on duty in Richmond worked around the clock rigging and deploying drift mines down the James in the path of advancing Federal warships.

David Bradbury and several other Singer operatives attached to the La Vaca facility prepared a similar mine surprise for Admiral Porter and his small armada of gunboats steaming slowly up the Red River toward Shreveport, La. On April 15, the Singer group’s efforts there paid off when the hull of the Federal ironclad Eastport was damaged by a torpedo. Northern forces later destroyed the vessel to keep it from being captured.

About this time, Admiral David Farragut, flag officer of the Gulf Blockading Squadron, was massing his forces for an all-out attack on Mobile Bay. McClintock and Watson were in charge of Singer operations in the region, overseeing the anchoring of more than 100 torpedoes near Fort Morgan at major entrances to Mobile Bay.

On the morning of August 5, 1864, Farragut’s attacking squadron weighed anchor and steamed toward the mouth of the bay. Spearheading his attacking column were the recently arrived single-turret monitors Tecumseh and Manhattan. Perhaps fearing that his vessel might run aground in the narrow channel, Tecumseh’s captain disregarded Farragut’s orders and unwittingly turned his vessel’s bow westward into a submerged cluster of Singer mines, triggering a huge explosion. The massive iron ship rolled to one side and slipped beneath the waves in less than a minute.

The Federals prevailed in that engagement, but the sinking of Tecumseh would go down as the most decisive Confederate torpedo victory of the war—and perhaps the quickest and complete destruction of an enemy vessel ever witnessed.

McClintock and Watson soon managed to mine all the water routes leading to Shreveport. At Galveston, meanwhile, Dunn supervised the construction of one ironclad torpedo boat, and in nearby Buffalo Bayou Braman began fabricating a second. Both were being financed with $160,000 that General Edmund Kirby Smith, commander of the Confederate trans-Mississippi forces, had dedicated to the Singer project.

As the two huge ironclads were taking shape in Texas in the fall of 1864, attention in the East turned to the one vital Richmond rail link not in Grant’s hands—the supply line between the Confederate capital and the port of Wilmington, N.C. With Lee’s army entrenched before Petersburg and supplies barely trickling to his troops, Grant made plans to sever this last lifeline. Anticipating Grant’s move, Confederate leaders ordered Singer’s Richmond-based operatives southward. Planning to destroy a railway bridge over the Roanoke River, a fleet of nine Federal gunboats headed upriver. “When [they] nearly arrived at their destination,” a German naval historian wrote later, “the vessels were either sunk or severely injured by submarine mines. Thus the expedition ended in a most disastrous failure.”

In early April 1865, Richmond fell, triggering the government’s abandonment of the capital. Although the Confederate states east of the Mississippi then lay in ruins, Union forces had barely touched Texas and much of western Arkansas and Louisiana. With Galveston still open to blockade runners and military supplies readily available across the Rio Grande in friendly Mexico, diehard Confederates believed organized resistance might perhaps be prolonged indefinitely.

Optimistic that he could make a new start west of the Mississippi, Jefferson Davis and his caravan headed steadily south toward Charlotte. En route, Davis received the news that President Abraham Lincoln had been assassinated, and on May 2, 1865, he called his cabinet together for the last time and ordered the destruction of many official papers, in part to lighten the load that would be transferred to the West.

While Davis and remnants of his tattered government were playing a cat-and-mouse game with Federal cavalry, word of Lee’s surrender reached Kirby Smith in Shreveport. Smith immediately made plans to establish an army of 15,000 troops at Marshall, Texas, to be placed at Davis’ disposal upon his presumed arrival. In Houston Mag­ruder released a directive ordering the citizens and soldiers of Texas not to give up the fight. Furthermore, he stipulated, construction on the two mammoth Singer ironclads was to continue around the clock.

By this time, however, Confederate deserters had given the Federals off Galveston detailed descriptions of Singer’s boats. One report stated that the enemy “are building a torpedo boat at Goose Creek, One hundred and Forty feet long to be clad in rail road iron.” Another revealed that “one of the men saw what was shown to him as a torpedo boat lying in the main channel at Galveston. It was shaped like a box, with square corners, and was quite low in the water. He could not tell whether she was plated or not.”

On May 10, at about the same time the Galveston torpedo boat was readied for sea, Davis and a 40-person entourage were captured near Irwinville, Ga. The next day Benjamin and Leovy were overtaken and informed that the Confederate government was no more.

The last battle of the Civil War was fought near Palmetto Ranch on the Rio Grande on May 12-13, 1865. Ironically, it ended in a Southern victory. But the clock had run out on the Confederacy. The governors of Texas, Arkansas and Louisiana were convinced their armies would be no match for a determined Union invasion force and sent word to Smith to negotiate surrender terms.

In a final ironic twist of fate, the Singer Secret Service Corps ended its mission for the Confederacy not with a bang but a whimper. After wreaking destruction on Union forces on land and on sea for more than two years, Edgar Singer and his band of middle-aged Masons walked into a Federal office in La Vaca and simply signed parole papers.

This article was written by Mark K. Ragan and originally published in the November/December 2007 issue of Civil War Times Magazine. For more great articles, subscribe to Civil War Times magazine today!