After his appointment as assistant postmaster general of the United States during Cleveland's first administration (1885–1889), Stevenson fired many Republican postal workers and replaced them with Southern Democrats.

This earned him the enmity of the Republican-controlled Congress, but made him a favorite as Cleveland's running mate in 1892, and he was elected vice president of the United States.

During his term of office, Stevenson supported the free-silver lobby against the gold-standard men like Cleveland, but was praised for governing in a dignified, non-partisan manner.

[1] In doing so, Stevenson became the fourth vice president that post teamed with two different presidential candidates (after George Clinton, John C. Calhoun, and Thomas A. Hendricks).

He was the paternal grandfather of Adlai Stevenson II, a Governor of Illinois and the unsuccessful Democratic presidential nominee in both 1952 and 1956.

The family appears to have had some wealth, as a private chapel in the Archdiocese of St Andrews bears their name.

At some point, probably shortly after the Jacobite rising of 1715, the family migrated to County Antrim, Ireland, near Belfast.

Stevenson attended Illinois Wesleyan University at Bloomington and ultimately graduated from Centre College, in Danville, Kentucky; at the latter he was a part of Phi Delta Theta.

In a predominantly Republican area, the Democratic Stevenson won friends through his storytelling and his warm and engaging personality.

Letitia helped establish the Daughters of the American Revolution as a way of healing the divisions between the North and South after the Civil War, and succeeded the wife of Benjamin Harrison as the DAR's second president-general.

In 1869, at the end of his term as state's attorney, he entered law practice with his cousin, James Stevenson Ewing, moving with his wife back to Bloomington, Illinois, and settling in a large house on Franklin Square.

The Republican presidential ticket, headed by Rutherford B. Hayes, carried his district, and Stevenson was narrowly defeated, getting 49.6 percent of the vote.

In 1878, he ran on both the Democratic and Greenback tickets and won, returning to a House from which one-third of his earlier colleagues had either voluntarily retired or been removed by the voters.

He rose to become grandmaster of his Masonic chapter and founded the Bloomington Daily Bulletin in 1881, a Democratic newspaper that sought to challenge the Republican Pantagraph.

Stevenson directed the People's Bank and co-managed the McLean County Coal Company with his brothers.

There, Stevenson befriended William Freeman Vilas, a growing voice among Midwest Democrats and a friend of Grover Cleveland.

Like his predecessors, Stevenson removed tens of thousands of political opponents from postal positions and replaced them with Democrats.

Likewise, Carter Harrison III (the mayor of Chicago) threw his support behind Stevenson as a native son, believing that he could influence the state to vote Democratic.

Civil service reformers held out hope for the second Cleveland administration but saw Vice President Stevenson as a symbol of the spoils system.

Once he called at the US Treasury Department to protest against an appointment and was shown a letter he had written endorsing the candidate.

Stevenson told the treasury officials not to pay attention to any of his written endorsements; if he really favored someone he would tell them personally.

While on a yacht in New York Harbor that summer, Cleveland had part of his upper jaw removed and replaced with an artificial device in an operation that left no outward scar.

Stevenson, 60 years old, received a smattering of votes, but the convention was taken by storm by a 36-year-old former representative from Nebraska, William Jennings Bryan, who delivered his fiery "Cross of Gold" speech in favor of a free silver plank in the platform.

Much of the newspaper speculation about who would run as the party's vice-presidential candidate centered on Indiana Senator Benjamin Shively.

When reporter Arthur Wallace Dunn interviewed Shively at the convention, the senator said he "did not want the glory of a defeat as a vice presidential candidate."

Disappointed, Dunn said that he still had to file a story on the vice-presidential nomination, and then added: "I believe I'll write a piece about old Uncle Adlai."

Bryan preferred his good friend Towne, but Democrats wanted one of their own, and the regular element of the party felt comfortable with Stevenson.

Nevertheless, their effort failed badly against the Republican ticket of incumbent president William McKinley and Theodore Roosevelt.

By May 1899, the North American Trust Company had directors such as John G. Carlisle, Adlai E. Stevenson and Wager Swayne.

In 1909 he was brought in by founder Jesse Grant Chapline to aid distance learning school La Salle Extension University.