But the first action was to be the landing at Daiquiri, and here Tommy Hart was to get his chance at martial glory. An amphibious assault against a defended coast was a hazardous undertaking and the short time between the commanders’ meeting and D-day on 22 June did not provide much opportunity for planning. A naval force was quickly assembled under command of Captain Caspar F. Goodrich in the transport St. Louis, a converted passenger liner.
The Massachusetts had numerous boats, so it was decided that she should provide the expedition with ten rowboats of various sizes and a steam launch. The question was who to put in charge of the Massachusetts’s boats. Her executive officer, Lieutenant Commander Seaton Schroeder, doubtless thinking of the action four days earlier, nominated Midshipman Hart. Her captain, Francis J. Higginson, whom Hart believed did not like him, demurred, but after further consultation reluctantly agreed. Therefore, in the early morning hours of 22 June Tommy Hart found himself in a steam launch bobbing around amidst the assault force and in charge of the largest group of landing craft. The term landing craft is used loosely here; what he commanded were rowboats, the smallest capable of carrying thirty and the largest fifty combat-equipped infantrymen.
For the assault to begin at dawn on the twenty-second, Hart had to distribute his boats alongside several transports, including the St. Louis, and prepare to load assault troops after dark on the twenty-first. This task was duly accomplished and Hart was in place beside the St. Louis when the sun rose and the bombardment of the beachhead began. As he later recalled, “a large expenditure of ammunition ensued” but with little damage done except to trees on the beach, because the Spanish had chosen not to defend Daiquirí. It was just as well for the Americans, since the beach was open and considerable surf was running. Noting this, Hart decided to unload his boats at a small dock that projected out beyond the waves. Though a reasonable idea, this took considerable doing and the soldiers had to jump for handholds when the boats reached the top of the swells. Soon they were all scrambling up the rickety dock and Hart returned to the St. Louis for another load.
Other captains made directly for the beach with the result that a number of boats, especially the heavy metal ones from the transports, were stranded on the shingle. Because Hart had the largest, most powerful steam launch, Goodrich ordered him, upon his return to the St. Louis, to turn his landing boats over to someone else and go in and salvage as many metal boats as possible. This proved to be extremely difficult. Hart had only five men in the launch, so he had to rely on the soldiers on the beach for assistance in getting the “tin” boats waterborne. The method was to bring the launch to a point just beyond the surf, anchor, then have someone swim ashore with a line attached to a heavy rope. Once the man was ashore, the heavy rope would be pulled in and attached to the stranded boat.
All that sounds relatively simple, but here’s what Hart has to say about it:
Getting through the surf with the line took some doing. I found I had only one man besides myself who was a good enough swimmer for the job. He and I took turns at it and it took seven or eight hours to accomplish the task. We would swim through the surf, get our breath, call for help from the soldiers—and they were quite ready to give it, being bored by sitting in the bush all day long—and they would come out with plenty of manpower. Then they, by main strength, got the boat waterborne whereupon either I or the other swimmer got into her and off we went, the launch getting up her anchor and taking the salvaged boat where she belonged for further service.20
Having gotten very little sleep the previous night, Hart found this exertion grueling. By the end of the day he was virtually exhausted, so when he eventually brought his launch alongside the St. Louis he found the prospect of negotiating the accommodation ladder almost more than he could handle; in fact he didn’t even have the strength to get off his launch. His men offered to carry him, a suggestion which he refused. The prospect of that indignity gave him the motivation to get from the launch to the ladder “and there I stuck.” A marine officer on board sized up the situation and, without giving Hart the opportunity to refuse, went down, threw him over his shoulder—all 105 pounds of him—and carried him aboard.
Thus the army got ashore and thus Tommy Hart got his first letter of commendation. Captain Goodrich wrote Higginson of the Massachusetts about the “exceptional ability, skill and faithfulness” displayed by Midshipman Hart.21 Goodrich noted specifically the seamanship that Hart had displayed when the launch’s anchor chain parted and she was swept broadside into the surf. At that point the painter of the boat in tow got wrapped around the screw of the launch and it looked as though the launch would capsize with the possible loss of her crew. Yet Hart managed not only to clear the screw but to bring the launch and the boat safely out of the surf.
With the army ashore, the misunderstanding between the two commanders soon became apparent. Instead of making for the entrance to Santiago Harbor, Shafter drove inland and there was little that Sampson could do to change the three-hundred-pound general’s mind or course. Nevertheless, it was essential that the two commanders keep in close touch. For this purpose, the Vixen, a converted yacht capable of 16 knots, was detailed as a dispatch vessel. To augment her crew Hart was ordered from the Massachusetts, probably because of his skill in small-boat handling. It was another stroke of good fortune. For one thing, at this stage in the operations the Vixen had a far more active role to play than did the larger ships. For another, her commanding officer, Lieutenant Alexander Sharp, Jr., took a liking to Hart and soon a relationship, almost filial, developed between them.
Before the war Sharp served as naval aide to the assistant secretary of the navy, Theodore Roosevelt. Roosevelt and his Rough Riders were with Shafter and this gave Hart an opportunity to observe the future president at close, sometimes too close, quarters. The Vixen picked up the day’s dispatches and took them to Daiquirí or Siboney, then someone had to take them inland to the army and bring back replies. As chance would have it, there was only one officer-horseman on board the Vixen. Having gained experience by riding to school in Michigan, Tommy Hart qualified as a dispatch rider. Often Sharp would order Hart to take a message to Colonel Roosevelt and see if TR could come back to the Vixen for a chat. On at least four occasions there was enough of a lull on the battlefield to allow Theodore Roosevelt to accept the invitation. “He would be riding with an aide or two on each side,” Hart recalled, “always talking, and I rode on behind. It was very hot in Cuba at that time. Mr. Roosevelt, as the world knows, was one of these men who perspire very freely, and he was not clean at all. In fact, riding behind, I could always smell him.”22
As soon as Roosevelt arrived aboard he would disappear into the bathroom, which was still equipped as it had been by the yacht’s wealthy former owner. Shortly, a pile of dirty clothes would be passed out and into the hands of waiting mess boys who would hustle them below decks for laundering. Then after much steam, soap, and scrubbing a glistening Theodore Roosevelt would appear, dressed in Alexander Sharp’s clothes and ready for dinner. The wine stores were also much as the owner had left them, the Vixen having been very hastily commissioned. Sharp had the only key and never used it except when Roosevelt was on board, but his visits were deemed occasions worthy of vintage wines. The wine, the friendship, and no doubt the circumstance of sitting off an enemy coast in such palatial surroundings made these meals quite remarkable. “The talk,” Hart recalled, was splendid, since “Sharp was a man of the world, the second officer was too,” and Theodore Roosevelt was no mean raconteur. After dinner the future president would collect his clean clothes and disappear again into deepest Cuba. All in all these were memorable occasions for a young midshipman.
Soon Roosevelt and the rest of the army were