The first of the series showcased Theodore Roosevelt as a military hero and sportsman. When the Spanish-American War began in April 1898, Roosevelt resigned as assistant secretary of the Navy to organize the 1st U.S. Volunteer Cavalry Regiment, known as the “Rough Riders.” As commander of the regiment, Colonel Roosevelt gained fame when he and his men bravely charged up Kettle and San Juan Hills during an intense and important battle in Cuba.

In this cartoon, Roosevelt in military uniform sits atop a cavalry horse to which is tied a rifle (he was an avid big game hunter), boxing gloves (he had been on Harvard’s boxing team), and what appear to be bowling pins. While the telegraph machine suggests his penchant for publicity, his hesitancy reflects the real question of whether he genuinely wanted or would accept the nomination. He was ambitious to be president, but feared that the vice-presidency was a dead-end political job. Nevertheless, the opening in the nation’s second highest office following the death of Vice President Garret Hobart in November 1899 was attractive to the New York governor.

Roosevelt was very popular among Republicans, especially in the West. Senator Lodge privately urged Roosevelt, his close friend, to seek the nomination, and he promoted the governor’s attributes to President McKinley. Shortly after this cartoon appeared Roosevelt privately rejected Lodge’s entreaties and then told the press that he would “under no circumstances” accept the vice presidential nomination. However, enthusiasm for his candidacy refused to wane, and the “boss” of the New York State Republican machine, Senator Thomas C. Platt, came under increasing pressure from businessmen to get the pro-regulation governor out of Albany. On the other hand, McKinley’s campaign manager and chairman of the Republican National Committee, Senator Mark Hanna of Ohio, lobbied hard against Roosevelt’s nomination. He feared that the New York governor’s pro-regulation record would undermine the pro-business image that Hanna wanted the party to project. The assertive Roosevelt might also threaten the senator’s own influence in the administration.

In April, Roosevelt began expressing openness to accepting the vice-presidential nomination. Nevertheless, when he visited Washington in May, he left politicians with contradictory impressions about whether he did or did not want the office. McKinley may have preferred a less colorful running mate, but decided to leave the choice to convention delegates. On June 21, the president was unanimously nominated for a second term and Roosevelt received all but his own vote as the party’s vice-presidential nominee. He quickly accepted and ran an energetic campaign, traveling 21,000 miles on a nationwide speaking tour.