On May 15, 1898, Roosevelt and Leonard Wood surveyed their regiment at the San Antonio fairgrounds. The Rough Riders comprised frontiersmen, cowboys, hunters, and mining prospectors from southwestern territories, along with volunteers from diverse trades. Roosevelt recruited four former police officers and Ivy League athletes dubbed the millionaire recruits, including David Goodrich and John Greenway. Volunteer J. O. Wells described initial friction between the college men and the cowboys that quickly dissolved into camaraderie as the groups learned to respect each other.

Roosevelt observed that more regiment members had Confederate fathers than Union fathers, yet they united around their shared patriotism. The men trained rapidly, learning mounted cavalry tactics. He handpicked journalists to accompany the regiment and proposed a serialization to Robert Bridges of Scribner’s Magazine.

On May 29, they boarded trains for Tampa, arriving after four days to find absolute chaos due to the military’s lack of preparedness and confused bureaucratic oversight. Edith visited Roosevelt, staying at the Tampa Bay Hotel, and he wrote enthusiastically to his children about her tour of the camp.

The men learned most horses would remain behind, with only senior officers’ mounts going to Cuba, despite how the Rough Riders trained on horseback. Further disappointment came when a fraction of the Riders learned they wouldn’t deploy. On June 7, they received abrupt orders to reach Port Tampa by morning. After scheduled trains failed to appear, they commandeered coal cars.

At the chaotic port, Roosevelt raced his men aboard their assigned transport, the SS Yucatan, to claim their position before two other regiments arrived. They waited six sweltering days on the overcrowded ship with minimal food. On June 13, the massive convoy finally departed, and men faced both delight and seasickness.

The destination changed from Santiago to Daiquiri to avoid a Spanish naval squadron. On June 22, they arrived to find rough seas, high waves, and no proper harbor for landing.

The landing at Daiquiri was chaotic; two men drowned reaching shore. The Rough Riders joined the Second Brigade under Major General Joseph Wheeler and brigaded with the First and 10th Cavalry regiments under Brigadier General Samuel B. M. Young. They met Cuban rebel allies led by General Calixto García, whom Roosevelt initially underestimated. After a difficult jungle climb to a blockhouse, they raised an American flag.

During the treacherous unloading of officers’ horses, one of Roosevelt’s mounts drowned, but his other horse, Texas, survived. The regiment undertook a grueling eight-mile march to Siboney. General Young informed Wood of Spanish positions near Las Guasimas, and they planned a two-pronged attack for the next day.

The climb to the ridge was excruciating through dense jungle. Correspondent Richard Harding Davis spotted camouflaged Spanish soldiers, and fierce fighting erupted. A bullet narrowly missed Roosevelt’s head. Black soldiers from the 10th Cavalry arrived at a critical moment to provide support. The Spanish retreated after the Rough Riders suffered eight killed and 34 wounded. Roosevelt was devastated to find officers he admired among the dead. Vultures descended on the bodies.

American newspapers glorified the Battle of Las Guasimas, making the Rough Riders national heroes. On June 30, the advance toward Santiago began. When Generals Wheeler and Young fell ill, Wood took brigade command, leaving Roosevelt in sole command of the Rough Riders.

The advance stalled on July 1, leaving troops exposed to unseen fire. O’Neill refused to take cover and was killed by a Spanish bullet. Orders finally came to assault Kettle Hill. Roosevelt led the charge on horseback, his wrist nicked by a bullet. Men from other regiments, including Black soldiers from the Ninth and 10th Cavalry, joined the assault. Evidence suggests the 10th Cavalry reached the hilltop first. Davis wrote a vivid description of Roosevelt leading his men up the slope.

After taking Kettle Hill, Roosevelt led his force across a ravine and up San Juan Hill, driving out the Spanish. The hungry troops found the enemy’s dinner still cooking in a captured blockhouse. Volunteer Carl Lovelace praised Roosevelt’s coolness under fire and the bravery of the Black soldiers. General Wheeler suggested withdrawal, but Roosevelt vehemently opposed the idea.

On July 3, the men heard the American fleet destroying Admiral Pascual Cervera’s squadron attempting to escape Santiago Harbor. A flag of truce followed, and fighting ceased. Spain surrendered on July 17. By then, Roosevelt’s troops were wounded, sick, and half-starved. Roosevelt later recalled the charge up San Juan Hill as the most joyous experience of his life.

On August 15, the transport ship Miami arrived at Montauk, Long Island, to a hero’s welcome. The men entered Camp Wikoff for quarantine, many suffering from malaria, typhoid, dysentery, and yellow fever. President McKinley visited and greeted Roosevelt warmly; Secretary of War Russell Alger was less friendly. Edith and the children visited, and Alice was smitten with the soldiers. Journalist Jacob Riis visited, and he and Roosevelt shared a reflective moment watching a meteor fall into the sea. On September 13, Roosevelt gave an emotional farewell speech, saying goodbye to each man individually as he mustered out the troops.

Upon returning from Cuba, Roosevelt’s name was immediately raised for New York governor. Republican boss Thomas Collier Platt, though personally hostile to Roosevelt, recognized the war hero was the only candidate who could win for the divided party. At the Saratoga Springs convention, Chauncey Depew nominated Roosevelt, who accepted and launched a vigorous train campaign accompanied by Rough Riders. He narrowly defeated the Democratic candidate.

As governor, Roosevelt moved his family into the Albany executive mansion, where Edith modernized the gloomy residence and established a schoolroom. Roosevelt converted the billiard room into a gymnasium and sparred with boxing coach Mike Donovan, who recalled Roosevelt’s insistence on being hit hard.

Roosevelt cultivated the press to appeal directly to the public and bypass the party machine. Despite clashes, he managed relations with Platt to build support for his progressive agenda, which included civil service reform, forest conservation, fair taxation, labor improvements, and creation of a naval militia. Roosevelt often used his sister Corinne’s New York City home as an outpost for meetings and meals, and he prioritized conservation efforts, such as saving the Hudson River Palisades from quarrying.

A year into his term, Roosevelt quietly planned a presidential run for 1904, after McKinley’s term. In June 1900, he traveled to Las Vegas for a Rough Rider reunion, delivering a statesmanlike speech emphasizing the duties of peacetime citizenship. As the Republican convention approached, however, a movement built to nominate Roosevelt for vice president on McKinley’s ticket, as the previous vice president had died. Roosevelt initially refused, suspecting Platt’s plot to remove him from New York and fearing the vice presidency was powerless.

Despite his reluctance, genuine support built at the Philadelphia convention. Roosevelt delivered McKinley’s nominating speech before accepting the vice presidential slot, which Platt viewed as neutralizing his rival.

Roosevelt carried the campaign weight against Democratic candidates while McKinley stayed home with his ailing wife. Declaring himself to be as strong as a bull moose, Roosevelt embarked on an unprecedented whistle-stop tour, visiting nearly 500 towns and cities. On November 6, 1900, the McKinley-Roosevelt ticket won decisively.

Roosevelt was inaugurated as vice president on March 4, 1901. On September 2, 1901, at the Minnesota State Fair, he delivered a famous speech introducing the proverb, “Speak softly and carry a big stick” (175). The chapter notes that in four days, everything would change.