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Roscoe Conkling was born on October 30, 1829 in Albany, New York. His father, Alfred Conkling, was a member of the U. S. House of Representatives and a federal judge. His mother, Eliza Cockburn, was a cousin of Lord Chief-Justice Sir Alexander Cockburn of England.
At the age of seventeen, Conkling began the study of law under Joshua A. Spencer and Francis Kernan in Utica, New York. As a young man he was a strong abolitionist and became active in the Whig Party. He married Julia Catherine Seymour, sister of Horatio Seymour, who later became the Democratic Governor of New York. In 1848 Conkling made campaign speeches on behalf of Zachary Taylor and his fellow New York Millard Fillmore. He was admitted to the New York State bar in 1850, and in the same year he also became district attorney of Oneida County.
In 1852 Conkling returned to Utica, where he established a reputation as a very capable lawyer. He campaigned for the Whig Party initially, but was active in the movement that resulted in the formation of the Republican Party. The Republicans carried New York in the 1856 presidential election, thanks in part to the hard work of Conkling.
In 1858, Conkling was elected to his first political position, Mayor of Utica. Subsequently he was elected as a Republican to the 36th and 37th United States Congresses, holding office from March 4, 1859, to March 3, 1863. While a member of the House, he served as Chairman of the House Committee on the District of Columbia. His brother, Frederick Augustus Conkling, was also a Republican member of Congress at the time. Conkling was defeated for re-election by Democrat Francis Kernan in the 1862 mid-term election. From 1863 to 1865, during the Civil War, he acted as a judge advocate of the War Department, investigating alleged frauds in the recruiting service in western New York.
Conkling returned to congress in 1864, defeating Kernan for re-election. He served in the 39th and 40th Congresses from March 4, 1865 to March 3, 1867, serving on the Joint Committee on Reconstruction which drafted the Fourteenth Amendment to the Constitution. He was re-elected to the 41st Congress in November 1866, but did not take his seat. Instead in January 1867 he was elected as a U.S. Senator from New York, and re-elected in 1873 and 1879. During President Ulysses Grant's administration, Conkling was one of Grant's strongest supporters and one of the principal leaders of the Republican Party in the Senate. In 1873, Grant asked Conkling to accept an appointment as Chief Justice of the United States, but Conkling declined.
Conkling was active in pushing reconstruction legislation through Congress, and was active in the passage of the second Civil Rights Act of 1875. He served as Chairman of the Senate Committee on Revision of the Laws of the United States, as well as the Senate Committee on Commerce.
Conkling had a reputation as a womanizer. He was accused of having an affair with Kate Chase Sprague, daughter of Salmon P. Chase and wife of William Sprague IV. According to an oft repeated story, Sprague confronted the couple at the Spragues' Rhode Island summer home and chased Conkling with a shotgun. Some reports say that Conkling jumped from a window to escape his lover's husband, who chased Conkling with an old civil war musket in his hands.
Conkling was a leader of the Stalwart faction of his party, the faction that believed in the "spoils system", the practice of rewarding political supporters with government patronage, while requiring those in receipt of patronage to make assessed donations back to the party. Conkling clashed with the Rutherford Hayes administration in April 1877 when the Secretary of the Treasury John Sherman appointed a commission to investigate the affairs of the New York Custom House. The investigation brought to light extensive irregularities in the service, showing in particular that the federal office holders in New York were men hired for their faithful service to the local party organization. Hayes decided to remove Chester Alan Arthur, the Collector, and a number of other prominent Conkling supporters. In October of 1877, Hayes sent nominations of their successors to the Senate. Conkling orchestrated the rejection of the new nominations. He succeeded in blocking all the efforts of President Hayes and Secretary Sherman until January 1879, when new nominations were confirmed despite Conkling's opposition.
As the 1880 presidential election approached, Conkling became the leader of the movement to nominate Ulysses Grant for a third term in the Presidency. He had a high regard for Grant, and was hostile to the other two leading Republican candidates, Sherman, with whom he had come into conflict during Hayes' administration, and James G. Blaine, whose had been his political and personal enemy he had been for over 20 years. The convention nominated compromise candidate James A. Garfield on the 36th ballot. To appease the Grant Stalwarts, the Vice-Presidential spot on the ticket was offered to Conkling. supporter Chester Alan Arthur. Against Conkling's wishes, Arthur accepted the offer.
Garfield was elected President after deftly maintaining the support of both Conkling's faction, and the opposing faction, led by James G. Blaine (known as the "Half-Breeds"). After Garfield's inauguration, Conkling gave the President a list of men he wished to be appointed to federal offices in New York. Garfield selected Blaine as Secretary of State, and William Windom as Secretary of the Treasury, neither of whom were Conkling men. This angered Conkling. When Garfield nominated William H. Robertson, the leader of the opposing Half-Breed faction, for Collector of the Port of New York, this set Conkling over the edge. In protest, Conkling and his fellow Senator Thomas C. Platt, resigned from their positions in the Senate. Conkling egotistically believed that he would be re-elected by the New York legislature. (At the time, senators were chosen by their states' legislatures). Instead, he was defeated in the resulting legislature's vote, losing to the Half-Breed faction in the vote. Conkling's career in the Senate came to an end.
Afterward Conkling resumed the practice of law in New York City. When his former protege Chester Alan Arthur became President, Arthur refused to appoint Conkling to the cabinet. Instead Arthur nominated Conkling as an Associate member to the United States Supreme Court in 1882, and the nomination was confirmed in the Senate, but Conkling declined to serve. He was the last confirmed nominee to refuse to serve on the court.
Arthur's and Conkling's relationship was at an end. The Stalwart faction that Conkling led was opposed to civil service reform. Without Conkling's leadership, his Stalwart faction dissolved. When Arthur died in 1886, Conkling attended the funeral and mourned the loss of his former friend.
On March 12, 1888, during the Great Blizzard of 1888, Conkling attempted to walk three miles from his law office on Wall Street to his home on 25th Street near Madison Square. He made it as far as Union Square before collapsing. He contracted pneumonia and died several weeks later, on April 18, 1888. Conkling is buried at Forest Hill Cemetery in Utica. A statue of him stands in Madison Square Park in New York City.