Home Flashback Photos Destruction of the Caleb Cushing: Confederate Pirates in Maine

Destruction of the Caleb Cushing: Confederate Pirates in Maine

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A 23-year-old Confederate naval lieutenant made a spectacular show when he blew up the Union’s revenue cutter Caleb Cushing in Portland Harbor. The blast rang the ears of spectators on Munjoy Hill, 15 miles away.

The destruction of the USRC Caleb Cushing wasn’t exactly what Lt. Charles “Savvy” Read had planned.  He’d captured the Cushing so he could destroy other Union vessels.  Though his mission failed, he managed to sow fear in the North. If Confederate pirates could capture a 100-foot schooner under the nose of Union forts in Maine, they could strike anywhere.

During the wee hours of June 27, 1863, the Caleb Cushing had lain at anchor in the harbor of Portland, Maine,. Her captain had died the night before and half her crew had gone ashore on liberty.

Read had quietly slipped into the harbor with his men aboard a fishing vessel he captured, the schooner Archer. They dressed as fishermen. In the past few weeks, Read had used such deception to capture or burn 21 Union supply vessels. By the time he sneaked into Portland Harbor, 40 Union ships were looking for the Confederate pirates.

Charles Read

Born in Mississippi, Read graduated from the U.S. Naval Academy in 1860. He briefly served on the USS Powhaten until the Civil War broke out. Then he joined the Confederate State Navy as a midshipmen.

Charles Read

He would soon earn another nickname: Sea Wolf of the Confederacy. By 1862, he had fought in several sea battles until assigned to the cruiser CSS Florida as a second lieutenant.

The Florida then captured the Clarence, which carried coffee to Baltimore, off the coast of Brazil. Read won permission to  transfer part of the Florida crew to the captured Clarence and raid Union vessels.

With the Clarence’s papers in hand, Read evaded the Union blockade. Starting on June 6, 1863, he went on an astonishing tear.

First he burned or captured five Union supply ships. Then on June 12, the Clarence captured the much larger bark Tacony. Read transferred his crew to it, burned the Clarence and then captured or destroyed 15 Union vessels in 13 days.

Aware that Union Navy ships had started to search for the Tacony, Read moved his crew and supplies to the last vessel he captured, FV Archer. He then set fire to the Tacony. He wrote in his notebook, “The latest news from Yankeedom tell me that there are over 20 gunboats in search of us,” wrote Read in his notebook. “No Yankee gunboat would even dream of suspecting us.”

Capture of the Caleb Cushing

On the night of June 26, the Archer anchored in Portland Harbor between Munjoy Hill and Fort Gorges. Read hatched his plan. He’d torch two gunboats under construction, then steal the Caleb Cushing.

With two cannon, plenty of gunpowder and a skeleton crew, the 100-foot schooner Caleb Cushing made a tempting target. Early in the morning, Read and his men disguised themselves as fishermen, then boarded two boats. They rowed with muffled oars to the Cushing and quickly boarded her.

It was over in less than 10 minutes.

With pistols and cutlasses, the Confederates overtook the watchmen, then divided in two. Some captured the crew and clapped them in irons, the rest captured the officers.

But it took some time to raise the cutter’s anchor. By then the tide had turned and the light wind didn’t fill the Cushing’s sails.

When dawn broke, the revenue cutter hadn’t made it out of reach of the Union gun batteries on shore. Read decided against setting fire to the gunboats and set out for sea.

He planned to send his prisoners from the Cushing onto the Archer after moving the Archer’s supplies to the Cushing. But two steamers overtook the Cushing. The Archer instead sailed 20 miles out to sea.

Chasing the Caleb Cushing

The next morning, the Cushing crew returned from liberty and discovered, to their alarm, their ship had disappeared. They notified the collector of customs,  Jedediah Jewett.

Fort Preble

Jewett and Mayor Jacob McClellan reacted quickly. They knew that Lt. Dudley Davenport, who’d taken command of the Cushing when her captain died, had been born in Georgia. The two men figured Davenport had made off with the cutter, loaded with ammunition and shot, and deliver her to the Confederate side.

They chartered two private steamships, the Chesapeake and the Forest City, to go after the two sailing vessels. A couple of small cannon  were put on board. Jewett and McClellan recruited infantrymen from Fort Preble. By 10 a.m. they were off.

The Cushing, powered by sail, couldn’t outrun the steamers, which soon overtook her.

The Forest City first engaged the captured cutter as people tried to watch through spyglasses on Munjoy Hill. The captain ordered the pilot, a civilian, to run down the fleeing schooner, but the Cushing tacked and headed straight for the steamer. The Confederates opened fire, though the shots fell short. The captain of the Forest City had to fall off because of the civilians aboard. They thought they were on a pleasure trip of the harbor.

“The accumulated advice and disjointed comments of these bewildered the captain, who stopped his boat and awaited the arrival of the propeller Chesapeake,” according to an official report of the engagement.

The Chesapeake had more speed and protective bales of cotton on deck. As she approached the Cushing, Capt. William f. Leighton planned to rake her with cannon fire, while the soldiers on board shot Confederates on deck. Then they’d board the vessel with bayonets.

The Caleb Cushing and the Archer

Dutch Cheese

But the Cushing’s 32-pound gun only seemed to have five rounds in it. The Confederates fired grapeshot at the Chesapeake, but didn’t do much damage. And it was strange shot — nails, stone, bits of metal. Finally Read abandoned the Cushing. Longboats filled with Confederates and Yankee prisoners — no one could tell which was which — rowed away from the cutter.

A longboat approached the Chesapeake, filled with men waving white handkerchiefs. Several men aimed their guns at what they thought were the Confederate pirates. Captain Leighton drew his pistol and threatened to kill anyone who fired a shot.

They would have killed their own men, including Lt. Dudley Davenport.

Davenport had hidden the shot in a secret locker off his quarters and locked the powder in a magazine. Read had questioned Davenport, telling him he should be ashamed as a Southern man not to give him the key or tell him where to find the ammunition. Davenport refused to give up the key or tell Read where he’d hid the shot.

During the skirmish, one of the Confederates brought a large ball of Dutch cheese above deck, and they stuffed it into the heavy gun and fired it at the Chesapeake. It scored a direct hit, splattering the vessel and bewildering everyone aboard.

That may have been the moment Read realized he was overmatched. He ordered his men into longboats for an attempted escape. Before he climbed in with them he set the Cushing on fire. Around 2 p.m., it exploded.

U.S.S. Caleb Cushing, destroyed by Confederate Rebels in Portland, 1863. Source: Maine Historical Society.

U.S.S. Caleb Cushing, destroyed by Confederate Rebels in Portland, 1863. Source: Maine Historical Society.

The Caleb Cushing Sinks

A reporter, aboard one of the steamers, described the scene.

A terrific explosion shakes the very heavens. The smoke rolls up in vast columns, fragments of shells, masts and spars and blackened timbers are seen hundreds of feet in the air, falling all around, the cutter begins to sink, her stern disappears, the guns fall off the deck into the fathomless deep, she careens, she gives on lurch — and the Caleb Cushing sinks beneath the waves.

Forest City, meanwhile, went after the Archer and soon caught up with her.

The steamer overtook the longboat that held Read and his crew. They waved white handkerchiefs and displayed Masonic signals, which some of the federal soldiers recognized. When Read surrendered, he was treated as a prisoner of war rather than a pirate. No one aboard the steamer, including its commander had any idea their prisoners were the same Confederate pirates 40 Union ships had been pursuing.


Crowds lined the docks when the two steamers brought their prisoners ashore. Some wanted to lynch them. Perhaps because their guards belonged to the freemasonry brotherhood, the prisoners made it safely to Fort Preble.

Somehow, souvenir hunters got hold of their spare clothing and distributed them among the people of Portland. Read gave an interview to newspaper reporters from his prison cell, hinting the Confederates planned more such raids on the North.

For his safety, the army sent Read to Fort Warren in Boston, where he escaped several times only to get caught. He was finally sent to Richmond in exchange for a Union prisoner.

With thanks to Sea Wolf of the Confederacy by David W. Shaw. This story updated in 2022. 

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