His father was Daniel Dole (1808–1878), principal at Oahu College (known as Punahou School after 1934), and his mother was Emily Hoyt Ballard (1808–1844).

Dole won the 1884 and 1886 elections to the legislature of the Hawaiian Kingdom as a representative from Kauaʻi,[8] serving from 1884 to 1887, during which time he was active in securing the constitution of 1887.

[9] King Kalākaua appointed Dole a justice of the Supreme Court of the Kingdom of Hawaii on December 28, 1887, and to a commission to revise judiciary laws on January 24, 1888.

[14] With Grover Cleveland's election as President of the United States, the Provisional Government's hopes of annexation were derailed for a time.

The Blount Report of July 17, 1893, commissioned by President Cleveland, concluded that the Committee of Safety conspired with U.S. ambassador John L. Stevens to land the United States Marine Corps, to forcibly remove Queen Liliʻuokalani from power, and declare a Provisional Government of Hawaii consisting of members from the Committee of Safety.

On November 16, 1893, Albert Willis presented the Queen with Cleveland's request that she grant amnesty to the revolutionists in return for being restored to the throne.

Though she later denied ever having recommended any such thing, her alleged attitude lost her the goodwill of the Cleveland administration, which thereupon recognized the Republic of Hawaii on July 4, 1894.

Dole in turn appointed Thurston to lead the lobbying effort in Washington, D.C., to secure Hawaiʻi's annexation by the United States.

Dole's government secured diplomatic recognition from every nation that had recognized the Kingdom of Hawaii, and weathered several attempts to restore the monarchy, including a January 1895 counter-rebellion led by Robert William Wilcox.

Queen Liliʻuokalani abdicated and, under duress, swore allegiance to the Republic of Hawaii, declaring, "I hereby do fully and unequivocally admit and declare that the Government of the Republic of Hawaii is the only lawful Government of the Hawaiian Islands, and that the late Hawaiian monarchy is finally and forever ended and no longer of any legal or actual validity, force or effect whatsoever.

[18] As president of the republic, Dole traveled to Washington, D.C., in early 1898 to personally urge annexation of Hawaii by the United States.

[22] President Dole and his party took off for Washington D.C via railroad, using a private railcar called "Guadalupe", supplied by Henry E. Huntington.

Under the terms of the Resolution, Dole retained the powers he previously exercised as President of Hawaii while Congress developed a new Hawaiian territorial frame of government.

Later, when one was established through the Hawaiian Organic Act, President William McKinley appointed Dole as the first governor of the Territory of Hawaii.

Dole assumed the office on June 14, 1900, but resigned November 23, 1903, to accept an appointment by President Theodore Roosevelt as judge for the U.S. District Court of Hawaii after the death of Morris M. Estee.