On the night of April 23, 1865, while the USS Vindicator was lying on the east side of the Mississippi River, opposite the mouth of the Red River, her commander, Acting Master Daniel P. Slattery was summoned to the observation deck by Pilot Wiley Jones. Jones had noticed, by the light of the moon, a trail of smoke some distance up the Red River, heading for the Mississippi. Anticipating the expected attempt to break through the Union blockade by the Confederate ram Webb, Slattery ordered his vessel prepared for battle.

It had been exactly two weeks since Lee's surrender at Appomattox and some eight days since the death of President Abraham Lincoln in Washington, D.C. It was in this atmosphere of the twilight of the Confederacy, that Lieutenant Charles W. Read, veteran of several ventures against Union shipping had commanded the Webb in one final act of naval defiance in home waters against the blockading Squadron. He had been ordered to take command of the Webb and to attempt to sneak through the Union vessels patrolling the Mississippi River, as well as the blockaders at sea, then to cruise against commercial vessels.

A side wheeled tug, the William H. Webb had been constructed in New York in 1856 and had been purchased by the Southern Steamship company. In May 1861, after the outbreak of hostilities, she was issued a privateers commission and succeeded, on May 24th, in capturing three whalers. Later she was used as a transport for the army before being converted into a ram for use on the Red and Mississippi Rivers. Her ultimate moment of glory came on February 24, 1863, when, together with the recently captured Queen of the West, she assisted in battering the U.S. ironclad Indianola into submission, near Palmyra Island, on the Mississippi River. In March, 1863, after the USS Hartford ran the gauntlet past the Vicksburg batteries, the Webb retreated up the Red River, above Alexandria, where she had remained virtually inactive until the final months of the war.

In early 1865, control of the Webb was transferred to the Confederate States Navy, and, on March 31, 1865, Charles Read took over command of the vessel, which he found lacking in arms, supplies and personnel. He took the vessel to Shreveport, where, with the help of General Kirby Smith, department commander, his requisitions were immediately tended to. The Webb was supplied with a 30-pounder Parrott gun and two small iron 12-pounders; carpenters tended to necessary renovations; wood was taken on as fuel, cotton as protective shields and personnel enlisted to man the vessel. Read was well aware of the dangers accompanying the move and of the several Union vessels guarding the mouth of the Red River, so his plan was to leave Alexandria on the night of April 22, giving him enough time to reach the Mississippi in about 24 hours. This would enable him to make the passage in darkness, lessening the risk of discovery. He also planned to cut the telegraph wires at intervals to prevent word of his move from reaching Forts Jackson & St. Philip, below New Orleans. He would also avoid attacking any of the enemy's vessels unless they attempted to stop him. In such an emergency, the Webb would carry five torpedoes, one of which was mounted on a spar.

The Webb actually left Alexandria early on the morning of the 23rd and had reached the Mississippi River by about 8.30 that night. In spite of the precautions taken by the Union fleet, she managed to slip through the net and pass the vessels guarding the mouth of the Red River practically unmolested. Only one shot had been fired at the Webb by the USS Manhattan and then a series of blunders allowed the Confederate vessel to continue with almost no pursuit by the enemy. With a few exceptions, Read's men were able to cut the wires along the route, keeping his enemy virtually in the dark about his movements. However, at least one message managed to get through to New Orleans, warning of her approach.

Some miles above New Orleans, the Webb hoisted a United States flag at half mast in an attempt to mislead the enemy into believing she was a transport. She passed the city about midday, but her deception having failed she was fired upon by the Union vessels with but little damage being inflicted. At least one shot missed the Webb and damaged a couple of private dwellings in the city itself, causing an estimated $150 worth of damage, for which the owners later attempted to claim compensation.

As soon as the Webb was fired upon, she hoisted the Confederate colors and continued steaming south, past New Orleans. Some 25 miles below the city, the USS Richmond was spotted heading her way, and, finding no other alternative, Read ordered the vessel run ashore at McCall's Point, and abandoned. At about 4.30 p.m., after being set alight, she blew up, the crew having escaped into the swamps, with the exception of two who were captured within minutes. One account also notes that an unnamed sailor was blown up with the vessel. The majority of the rest of the crew were captured within 48 hours by pursuers from the Union army and navy.