He tried a variety of jobs before gaining employment as a cartoonist, initially working at several newspapers on the West Coast, including The San Francisco Examiner, purchased by William Randolph Hearst.

Working with columnist Alfred Henry Lewis, Davenport created many cartoons in opposition to the 1896 Republican presidential candidate, former Ohio governor William McKinley, and Hanna, his campaign manager.

The President in turn proved helpful to Davenport in 1906 when the cartoonist required diplomatic permission to travel abroad in his quest to purchase pure desert-bred Arabian horses.

Davenport's later years were marked by fewer influential cartoons and a troubled personal life; he dedicated much of his time to his animal breeding pursuits, traveled widely, and gave lectures.

Cooped up inside during the winter of 1870–1871,[6] in part because the entire family was quarantined on account of the smallpox outbreak that had killed Florinda,[3] Timothy told Homer stories of Arab people and their horses.

In his early days as a newspaper tycoon, Hearst followed Davenport's cartoons in the Chronicle, and when the cartoonist became well known for his satires of figures in the 1894 California gubernatorial campaign, hired him, more than doubling his salary.

In September 1895, having lost most of its circulation and its advertisers over the past year, Cincinnati publisher John R. McLean made his New York Morning Journal available at a price within Hearst's means, and he bought it for $180,000.

Under editor-in-chief Willis J. Abbot, the well paid staff included foreign correspondent Richard Harding Davis, columnist Alfred Henry Lewis, and humorist Bill Nye.

[30] In 1896, a presidential election year, Davenport was sent to Washington to meet and study some of the Republican Party's potential candidates, such as Speaker of the House Thomas B. Reed.

[35] The resultant caricature of Hanna was given props such as moneybags and laborer's skulls to rest his feet upon, as well as cufflinks engraved with the dollar sign to wear with his plaid businessman's suits.

Even so, Davenport felt the figure seemed to lack something until the cartoonist took the dollar signs from the cufflink and placed them inside every check of the cartoon Hanna's suit.

Davenport likely acted at the suggestion of his cartoonist colleague at the Journal, M. de Lipman, who had depicted McKinley as Buddha in a loincloth with Hanna as his attendant, robes ablaze with an array of dollar signs.

West Virginia Senator Nathan B. Scott remembered being with Hanna as he viewed his caricature wearing a suit covered with dollar signs, trampling women and children underfoot, and hearing the Ohioan state, "that hurts".

He may be indifferent to God and the devil; regardless of heaven and hell; careless of the sanctions of human law so long as he can escape the penitentiary or the gibbet; but he shrinks from the pillory of the cartoon in which he is a fixed figure to be pointed at by the slow unmoving finger of public scorn."

[52] He was impressed by the large muscles of the work, and immediately conceived of it as representing America's powerful corporate trusts, the status of which was then a major political issue.

[52] In 1897, Davenport was sent to Carson City, Nevada, to cover the heavyweight championship fight between boxers Bob Fitzsimmons and Jim Corbett, a match heavily promoted by the Journal.

Senator Thomas C. Platt, (R-NY), did not pass, but the effort inspired Davenport to create one of his most famous works: "No Honest Man Need Fear Cartoons.

Also a subject of Hearst's cartoonists was McKinley's running mate, war hero and New York Governor Theodore Roosevelt, presented as a child with a Rough Rider's outfit and little self-control.

He also began to devote large periods to other activities; in 1905, he spent months in his home state of Oregon, first visiting Silverton and then showing, at Portland's Lewis and Clark Exposition, the animals he bred.

[71] Upon learning that these horses had remained in America and had been sold at auction, he sought them out,[64] finding most of the surviving animals in 1898[70] in the hands of millionaire fertilizer magnate Peter Bradley of Hingham, Massachusetts.

[74] In 1906, Davenport, with Bradley's financial backing,[75] used his political connections, particularly those with President Theodore Roosevelt, to obtain the diplomatic permissions required to travel into the lands controlled by the Ottoman Empire.

[76] To travel to the Middle East and purchase horses, Davenport needed to obtain diplomatic permission from the government of the Ottoman Empire,[76] and specifically from Sultan Abdul Hamid II.

[83] Before Davenport left Constantinople to travel to Aleppo and then into the desert, he visited the royal stables,[84] and also took advantage of an opportunity to view the Sultan during a public appearance.

[85] He displayed his artistic ability and talent for detail by sketching several portraits of Abdul Hamid II from memory about a half-hour after observing him, as Davenport believed the ruler unwilling to have his image drawn.

Davenport compared his appearance as a melding of the late congressman from Maine, Nelson Dingley, with merchant and philanthropist Nathan Straus, commenting of the Sultan, "I thought ... that no matter what crimes had been charged to him, his expressionless soldiers, his army and its leaders were possibly more to blame than he.

[88] One reason for Davenport's success in obtaining high-quality, pure-blooded Arabian horses was his (possibly accidental) decision to breach protocol and visit Akmet Haffez, a Bedouin who served as a liaison between the Ottoman government and the tribal people of the Anazeh, before calling upon the Governor of Syria, Nazim Pasha.

[101] Davenport also purchased horses from the Crabbet Park Stud in England, notably the stallion *Abu Zeyd,[b] considered the best son of his famous sire, Mesaoud.

[110] In Morris Plains, the Davenports hosted large parties attended by celebrities, artists, writers, and other influential people of the day, including Ambrose Bierce, Lillian Russell, Thomas Edison, William Jennings Bryan, Buffalo Bill Cody,[112] Frederic Remington, and the Florodora girls.

[115] By 1905 he started a pheasant farm on his property in Morris Plains, gathering the birds he had kept on the west coast, and buying others from overseas using the profits from his first published book of cartoons.

[121] Homer initially returned to New York to live,[120] but soon suffered a breakdown; he spent months recuperating in a resort hotel in San Diego, California, at the expense of his friend, sporting goods mogul Albert Spalding.