After a disorganized and ineffective campaign, Parker was defeated by 336 electoral votes to 140, carrying only the traditionally Democratic Solid South.

[6] After his election, Hill appointed Parker to fill an 1885 vacancy on the New York Supreme Court created by the death of Justice Theodore R.

In November 1897, Parker successfully ran for the post of Chief Judge of the Court of Appeals, defeating Republican William James Wallace.

His judicial opinions were noted "for their forceful diction, comprehensive grasp of the fundamental questions involved, unsparing labor in citing precedents, close reasoning, and their tendency to disregard merely technicalities."

[8] During his time as Chief Judge, Parker and his wife sold their Kingston home and bought an estate in Esopus on the Hudson River, calling the house "Rosemount".

[3] As the 1904 presidential election approached, the Democrats began to search for a nominee to oppose popular incumbent Republican president Theodore Roosevelt, and Parker's name arose as a possible candidate.

[6] The 1904 Democratic National Convention was held in July in St. Louis, Missouri, then also hosting the 1904 World's Fair and the 1904 Summer Olympics.

[10] Radicals in the party supported publisher William Randolph Hearst but lacked sufficient numbers to secure the nomination due to opposition from Bryan and Tammany Hall, the powerful New York political machine.

[12] Parker's long service on the bench proved to be an advantage in his nomination, as he had avoided taking stands on issues that divided the party, particularly that of currency standards.

[12] Henry G. Davis, an elderly West Virginia millionaire and former senator, was selected as the vice presidential candidate in the hope that he would partially finance Parker's campaign.

The "free silver" movement, a key plank for the party in 1896 and 1900, was popular among indebted Western farmers who felt that inflation would help them repay their debts.

[16] The telegram sparked a new debate and fresh opposition from Bryan, but the convention eventually replied to Parker that he was free to speak on the issue as he liked.

[13] National support for Parker began to rise, and Roosevelt praised his opponent's telegram in private as "bold and skillful"[14] and "most adroit".

Parker then delivered a speech criticizing Roosevelt for his administration's involvement in Turkish and Moroccan affairs and having failed to give a date on which the Philippines would become independent of American control.

However, due to Esopus's remote location and the campaign's inefficient use of funds to bring in delegates, Parker received few visitors.

[18] In contrast, Roosevelt's campaign, headed by George Cortelyou, organized committees to appeal specifically to demographics including Jewish, black, and German-American voters.

[21] John Hay, Roosevelt's Secretary of State, wrote of Parker's poor showing to Henry Adams, calling it "the most absurd political campaign of our time".

[23] In late October, he also went on a speaking tour in the key states of New York and New Jersey, in which he reiterated the president's "shameless exhibition of a willingness to make compromise with dignity".

[30] In 1913, Parker was appointed lead trial counsel in the impeachment of New York governor William "Plain Bill" Sulzer.

Sulzer faced eight articles of impeachment, alleging that he made and filed a false statement regarding his campaign accounts, perjured himself in verifying the statement concerning his campaign accounts, bribed witnesses and fraudulently induced them to withhold evidence from the legislative committee investigating his misconduct, suppressed evidence by threatening witnesses, dissuaded a witness from appearing before the committee pursuant to a duly authorized subpoena, used campaign contributions to speculate in the stock market, promised and threatened to use his influence as governor to affect the votes or political actions of certain members of the general assembly and used his authority and influence as governor "to affect the current prices of securities listed and selling on the New York Stock Exchange."

Parker believed this proposal to be a danger to the nation's constitutional order, siding with conservatives in the GOP like William Howard Taft and Elihu Root to oppose Roosevelt's candidacy.

While Wilson was more progressive than Parker's preferred candidate, Champ Clark, and held the endorsement of Bryan, he also came out against judicial recall.