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The mission itself was a failure. The MERRIMAC's steering gear was damaged by enemy fire and though the vessel sunk, it did not block the channel. Hobson and his crew were captured. They were all eventually exchanged, with Hobson becoming an overnight celebrity nationwide.

In hindsight, the U.S. forces were lucky that the effort did fail, as the Spanish fleet would have been trapped in the harbor with crews and guns still able to defend Santiago itself. For Spain, the situation would have been better if the effort had succeeded, perhaps resulting in much less loss of Spanish life and a better bargaining position in peace negotiations.

Also, in an ironic twist, after the loss of the Spanish naval squadron in the Battle of Santiago, the Spanish themselves attempted to block the harbor entrance by sinking the REINA MERCEDES in the same area where the U.S. Navy attempted to sink MERRIMAC. This attempt was also a failure.
 

Hobson studied the problem and determined that there were two methods that could be used to sink the vessel. One would be to use a series of explosives, termed "torpedoes"; the second involved cutting rivet heads from six hull plates. The torpedo method as chosen since it would take less time to prepare. The "torpedoes" to be used consisted of ten separate watertight canisters filled with about 78 pounds of brown powder and strapped to the port side of the vessel below the waterline. The torpedoes were rigged to to blown electronically. The port side was used since this side would be the "forward" side as the ship turned into position, causing the inrush of water to be more rapid. I addition, all ports, hatches, doors and seacocks were rigged to be open or opened rapidly to increase the speed in which the vessel would fill with water.

The system, if it worked, would sink the vessel within a minute and a quarter. However, the electrical firing mechanisms were not the most reliable. In an effort to ensure sinking if some or all of the electrical primers failed, Hobson requested two actual automobile (Whitehead) torpedo warheads from the USS NEW YORK. The two hundred pounds of guncotton from the torpedoes would be placed in the most critical location, and also rigged for electrical firing. The request for the warheads was rejected by Admiral Sampson, who stated that "two hundred pounds of guncotton on the inside would blow everything to the devil" and would most likely kill the volunteer crew.

The plan was to take the MERRIMAC into the channel, put the helm hard to port, and drop the bow anchor with specific length of chain. Shortly afterwards, when the vessel was completely athwart the channel, the stern anchor would be dropped. at this point, the torpedoes would be blown, seacocks opened, and the vessel would sink, blocking the channel. The small all-volunteer crew would meet and escape via a catamaran hoisted over the side, and sail back to the U.S. fleet.

Problems beset the plan as it was rushed to be readied in a very short time. Batteries had to be depended on to fire the torpedoes, and there were initially only enough batteries to fire six of the ten explosives. Preparations ran behind schedule, but, finally, almost everything was in readiness.

The first attempt to sink the vessel on the night of June 1, 1898 was called off and additional work was done on the vessel allowing the last four torpedoes to be able to fire.

The next attempt was made on June 3, 1898. Almost immediately, the hard-luck collier began to act up. Only three of the ten torpedoes responded to testing and were able to be fired. Still, the MERRIMAC charged into the channel under full steam. A Spanish picket boat hidden near the channel entrance opened up on the MERRIMAC with its rapid fire guns. At point blank range, the plucky Spanish vessel fired directly at the MERRIMAC's steering gear. The gear, already in bad conditon, failed. This was one of the most vulnerable points on the veesel, and Hobson knew it. Without steering control, the mission was badly compromised.

The MERRIMAC continued onward. The bow anchor was dropped and the first torpedo was fired. Unfortunately, the only other torpedo to fire was number five. The three others that were still functional as the vessel entered the channel had been damaged by gunfire and were no longer operable.

The stern anchor was dropped, but the vessel , not in the planned position, dragged its anchors and forged ahead. Batteries opened on the vessel on both sides. The MERRIMAC began to sink almost across the channel, but the strong current began to straighten her out. The vessel continued to move down the channel into the harbor and into greater danger. She actually crossed the bows of the Spanish vessels REINA MERCEDES and PLUTON which both unleashed fire and Whitehead torpedoes on the MERRIMAC.

The Spanish had mistaken the incoming vessel as some sort of man-o'-war attempting to enter the harbor and attack the Spanish fleet. Some of the Spanish gunners apparently fired on the muzzleblasts of guns they thought were aboard the incoming vessel. Crossfire over the vessel occurred. The Spanish suffered casualties, which they did not learn until later, were the result of friendly fire.

The MERRIMAC sunk, but not in a position that could block the channel. Hobson's crew, in spite of the severe fire, were relatively unhurt. They found the catamaran overturned, and a strong current entering from the sea, away from the U.S. fleet. It was apparent that they could not swim against the current, so Hobson and his crew clung to the overturned catamaran until they were picked up by a steam launch the next morning. The launch was that of Spanish Admiral Cervera, who was aboard.

Hobson's crew became prisoners of war, and were well treated by their captors. Hobson later wrote of how he was received aboard the REINA MERCEDES. They were finally exchanged on July 6, 1898.

The mission had proved to be a failure. The channel was not blocked by the vessel, but this act of bravery accorded Hobson and his crew hero status, with the entire crew, including Hobson, being awarded the Congressional Medal of Honor.

George Charette - Fire torpedo #2 and #3 (age 29, gunner's mate first class from the USS NEW YORK. At this time, he had served in the navy for 14 years. He was from Lowell, MA).

Randolph Clausen, Fire torpedo #5 (age 28, coxswain of the USS NEW YORK. He had been in the navy for just over a year. Clausen was from Boston, MA).

Osborn Warren Deignan - Helmsman, fire torpedo #4  (age 21, coxswain of the collier MERRIMAC. Deignan had joined the navy just days before the formal declaration of war on Spain. He was from Stuart, Iowa).

Francis Kelly - Operate engines, fire torpedo #8 (age 28, water tender aboard the collier MERRIMAC. He had joined the navy just days before the formal declaration of war on Spain. He was from Boston, MA).

Daniel Montague - Fire torpedo #7 (?)  (age 29, chief master-at-arms from the USS NEW YORK. He had served in the U.S. navy for 7 years, after previously serving in the British Royal Navy. He was born in Ireland).

J. C. Murphy - Drop anchor, fire torpedo #1 (coxswain, USS IOWA).

George F. Phillips - Operate engines, fire torpedo #6 (age 34, machinist first class aboard the collier MERRIMAC. Phillips had joined the navy just days before the formal declaration of war on Spain. He was from Boston, MA).

Hobson, Richmond Pearson, The Sinking of the Merrimac. (Annapolis: Naval Institute Press, 1987, ISBN: 0-87021-632-5, a reprint of an 1899 edition).

Robert M. Wein, correspondence with author (sole living descendant of Daniel Montague).

"Schley Court of Inquiry in Session," Reno [Nevada] Evening Gazette. September 30, 1901, p. 1