Adlai Stevenson was born in Christian Country, Kentucky, on October 23, 1835, to Eliza Ann Ewing Stevenson and John Turner Stevenson, a tobacco farmer. In 1852, a major frost killed the family's tobacco crop, which prompted the family to move to Bloomington, Illinois. In Bloomington, a young Adlai worked in his father's sawmill and taught school in order to earn money to attend college. He eventually enrolled in the Presbyterian-run Centre College in Danville, Kentucky, where he met his future wife, Letitia Green. He later attended Illinois Wesleyan University. Upon the death of his father in 1857, Stevenson returned to Bloomington where he studied law and was admitted to the Illinois bar in 1858. During the Civil War, he served as the master in chancery of Woodford County's circuit court and organized the 108th Regiment Illinois Volunteer Infantry. Following the war, he served a four-year term from 1865 to 1869 as prosecuting attorney for the 23rd judicial district. He then opened a successful law practice with his cousin, James Ewing. In 1866, Stevenson married Letitia Green after a lengthy courtship.
Although Stevenson had dabbled in politics - he campaigned for Stephen Douglas in his 1858 Senate race against Abraham Lincoln and served as a presidential elector during the 1864 election - his political career did not begin in earnest until 1874, when he defeated a Republican incumbent to become one of Illinois's few Democratic representatives to the House of Representatives. Stevenson served one term, but was defeated in 1876 by a Republican challenger who capitalized on the failing economy and the state's traditional status as a Republican stronghold. However, Stevenson ran again for the House seat in 1878 and won, serving until 1881.
In 1885, newly-elected President Grover Cleveland appointed Stevenson to be the first assistant postmaster general. The appointment was considered an honor, and Stevenson relished the opportunity to control a large portion of the spoils system. During his four-year tenure as assistant postmaster general, Stevenson replaced more than 40,000 Republican postal employees with Democrats, earning himself the nickname, "Headsman." After his term was completed, he returned to his law practice in Bloomington, Illinois. In 1892, the Democratic Party again nominated Grover Cleveland for President, and in a surprise to many observers (himself included), Adlai E. Stevenson was nominated as vice president.
As the vice presidential nominee, Stevenson provided needed balance to the ticket. His home state of Illinois was considered important to Cleveland's election hopes, and Stevenson's popularity there was seen as an asset. Additionally, Stevenson's views on currency reform contrasted favorably with those of Cleveland, who endorsed the gold standard, and helped broaden the appeal of the ticket. Moreover, Stevenson was an energetic and popular campaigner; his work as assistant postmaster general had earned him many allies in the Democratic Party. Cleveland won the election that fall, and Stevenson was sworn in as vice president on March 3, 1893.
Vice President Stevenson was both a fixture on the Washington social scene and an enthusiastic public servant. He regularly opened his offices to reporters and found a fair amount of pleasure in presiding over the Senate. In a notable occasion, he unknowingly almost became President of the United States when President Cleveland underwent surgery to remove a malignant growth from the roof of this mouth. Cleveland was eager not to cause panic on Wall Street with the prospect of a "soft money" proponent ascending to the presidency and had the operation performed in secret on a yacht in New York. Even members of the cabinet, including Stevenson, were largely unaware of the severity of Cleveland's health problem. The operation was a success, and the details of it were not made public until 1917.
As vice president, Stevenson traveled the country often. In the wake of the 1894 midterm elections in which the Democrats suffered heavy losses, he used this traveling as an opportunity to bridge the gap between the Eastern and Western factions of the Democratic Party. Although he was briefly considered as a possible presidential candidate in 1896, he received limited support and eventually endorsed Democratic candidate William Jennings Bryan, despite the reluctance of many Cleveland Democrats to do so. After leaving office, Stevenson had a brief respite from politics but reappeared as Bryan's running mate in the 1900 presidential election. Despite campaigning vigorously, the pair lost to the Republican ticket of William McKinley and Theodore Roosevelt.
After the defeat in 1900, Stevenson returned to private practice in Bloomington, Illinois, where he worked quietly until 1908, when he made an unsuccessful run for governor of Illinois. Following his loss, he finally retired from politics, living the quiet life of an elder statesman until his death on June 14, 1914. His grandson, Adlai E. Stevenson II, served as governor of Illinois and was nominated as the Democratic candidate for President in 1952 and 1956, losing both times to Dwight Eisenhower. His great-grandson, Adlai E. Stevenson III, served as a senator for Illinois, twice ran for governor, and was himself considered a contender for the vice presidential nomination in 1976.