Webb was decorated for his service as Captain of the CSS Teaser, part of the James River Squadron, during the Battle of Hampton Roads (1862).

[1] Webb departed from Norfolk, Virginia on February 7, 1847, traveling to the Pacific Ocean by way of Cape Horn, eventually reaching Japan in 1854.

Buchanan wrote later: "The general order under which the gunboat squadron went into action required that, in the absence of all signals, each commanding officer was to exercise his own judgment and discretion in doing all the damage he could to the enemy and to sink before surrendering.

John Randolph Tucker, commanding the rest of the James River Squadron, ran past the shore batteries to join the battle, with the CSS Teaser "puffing with all the energy of a short-winded tug.

[6] Their escape was miraculous, as they were under a galling fire of solid shot, shell, grape and canister, a number of which passed through the vessels without doing any serious injury, except to the Patrick Henry...[6]The squadron immediately joined in the battle with the CSS Virginia against the Union blockade and shore batteries.

When the Confederate ships charged with accepting the surrender and escorting the captured officers were fired upon by Union shore batteries, Buchanan then ordered another boat to burn her, with Webb's Teaser as cover.

Buchanan took pride in his gunboats: "Their judgment in selecting their positions for attacking the enemy was good; their constant fire was destructive, and contributed much to the success of the day.

In this case, Webb was made commander of the "Special Expedition", a squadron of small boats manned by sixty officers and men, on February 19, 1863.

What made this flotilla unusual, and hence its appellation of "special", was that the boats were armed with spar torpedoes, a highly controversial weapon of war that some considered "uncivilized".

[12] It was not at all uncommon to see a sailor rolling down to his boat, when they were called for exercise, with a quid of tobacco in his cheek and a torpedo slung over his back; and when it is recollected that each torpedo had seven sensitive fuses which a tap with a stick or blow with a stone was sufficient to explode and blow half the street down, it can readily be believed that we gave them a wide berth.

John Randolph Tucker ordered Webb to contact a local merchant and acquire the steamers "quietly and pleasantly if possible" or seize them, if not.

[13] While present when Admiral Du Pont's fleet crossed the Charleston Bar on April 6, 1863, Webb's squadron was not called into action that day.

[13] Commodore Josiah Tattnall III, Flag Officer commanded the southern region of the Confederate States, especially Savannah, Georgia.

[15] Considered by the citizens of Georgia to be the most powerful Confederate warship because of its fast speed of 7 knots, as well as its armament of four Brooke rifles, the Atlanta was difficult to maneuver.

Webb marshaled the CSS Atlanta, though, removing the boat of unnecessary comfort - including sanitation and ventilation, as well as fully outfitting it with weaponry.

[18] He told his crew: "I most earnestly wish that it had happened otherwise, but Providence, for some good reason, has interfered with our plans ..."[19] Meanwhile, the two boats escorting the Atlanta scurried upriver for safety.

His stranded ship would have become a slaughter-pen under a few more of the Weehawken's shots ...[19]However, the news stunned the South and Webb faced criticism even after the war from experienced naval officers.

[18] Criticism also fell on Secretary of the Navy, Stephen R. Mallory for his policy of replacing older officers with younger ones and for not firmly opposing Webb in his decision.

While in London, he took the Oath of Allegiance before Francis A. Adams, the U.S. Consul in that city, on 31 May 1865, and left England the next month, to return home to his native state of Virginia.