Early in 1952, while Stevenson was still governor of Illinois, President Harry S. Truman decided that he would not seek another term as president. Instead, Truman met with Stevenson in Washington and proposed that Stevenson seek the Democratic nomination for president; Truman promised him his support if he did so. Stevenson at first hesitated, arguing that he was committed to running for a second gubernatorial term in Illinois. However, a number of his friends and associates (such as George Wildman Ball) quietly began organizing a "draft Stevenson" movement for President; they persisted in their activity even when Stevenson (both publicly and privately) told them to stop. When Stevenson continued to state that he was not a candidate, President Truman and the Democratic Party leadership looked for other prospective candidates. However, each of the other main contenders had a major weakness. Senator Estes Kefauver of Tennessee won most of the presidential primaries and entered the 1952 Democratic National Convention with the largest number of delegates, but he was unpopular with President Truman and other prominent Democrats. In 1950 Kefauver had chaired a Senate committee that traveled to several large cities and held televised hearings into organized crime. The hearings revealed connections between organized-crime syndicates and big-city Democratic political organizations, which led Truman and other Democratic leaders to oppose Kefauver's bid for the nomination: "a machine politician and proud of it, [Truman] had no use for reformers who blackened the names of fellow Democrats." Truman favored U.S. diplomat W. Averell Harriman, but he had never held elective office and was inexperienced in national politics. Truman next turned to his Vice-President, Alben Barkley, but at 74 years of age he was dismissed as being too old by labor union leaders. Senator Richard Russell Jr. of Georgia was popular in the South, but his support of racial segregation and opposition to civil rights for blacks made him unacceptable to Northern and Western Democrats. In the end Stevenson, despite his reluctance to run, remained the most attractive candidate heading into the 1952 Democratic National Convention in Chicago.
In the 1952 campaign Stevenson also developed a strong dislike for Richard M. Nixon, then the GOP vice-presidential candidate. "Adlai literally loathed Nixon. No other person aroused such disgust; not even Joseph McCarthy...Friends who often wished he could be more of a hater were awed at the strength of his distaste for Nixon." A biographer wrote that "for Stevenson, Nixon was an ambitious, unprincipled partisan who craved winning, the exact personification of what was wrong with modern American politics...[for Stevenson] Nixon was an entirely plastic politician...Nixon was Stevenson's complete villain. Others sensed the potential for immorality that led to Nixon's humiliating resignation in 1974, but Stevenson was among the first." During the 1952 campaign Stevenson often used his wit to attack Nixon, and once stated that Nixon "was the kind of politician who would cut down a redwood tree, and then mount the stump and make a speech for [tree] conservation."
The journalist David Halberstam later wrote that "Stevenson [was] an elegant campaigner who raised the political discourse" and that in 1952 "Stevenson reinvigorated [the Democratic Party] and made it seem an open and exciting place for a generation of younger Americans who might otherwise never have thought of working for a political candidate." During the campaign, a photograph revealed a hole in the sole of Stevenson's right shoe. This became a symbol of Stevenson's frugality and earthiness. Photographer William M. Gallagher of the Flint Journal won the 1953 Pulitzer prize on the strength of the image.
Unlike 1952, Stevenson was an announced, active candidate for the Democratic presidential nomination in 1956. Initially, with polls showing Eisenhower headed for a landslide re-election, few Democrats wanted the 1956 nomination, and Stevenson hoped that he could win the nomination without a serious contest, and without entering any presidential primaries. However, on September 24, 1955, Eisenhower suffered a serious heart attack. Although he recovered and eventually decided to run for a second term, concerns about his health led two prominent Democrats, Tennessee Senator Estes Kefauver and New York Governor Averell Harriman, to decide to challenge Stevenson for the Democratic nomination. After being told by his aides that he needed to enter and win several presidential primaries to defeat Kefauver and Harriman, Stevenson entered and campaigned in the Minnesota, Florida, and California primaries. Stevenson was upset by Kefauver in the Minnesota primary, who successfully portrayed Stevenson as a "captive" of corrupt Chicago political bosses and "a corporation lawyer out of step with regular Democrats." Stevenson next battled Kefauver in the Florida primary, where he agreed to debate Kefauver on radio and television. Stevenson later joked that in Florida he had appealed to the state's citrus farmers by "bitterly denouncing the Japanese beetle and fearlessly attacking the Mediterranean fruit fly." He narrowly defeated Kefauver in Florida by 12,000 votes, and then won the California primary over Kefauver with 63% of the vote, effectively ending Kefauver's presidential bid.
His biographer Jean H. Baker wrote of Stevenson's two presidential campaigns in 1952 and 1956 that "what would be remembered...were not his public programs and ideas for a New America but, ironically, the private man – his character and personality, his wit and charm, his efforts to negotiate and keep the peace within the Democratic Party, his elegant speeches, and the grace with which he accepted defeat."
In Robin Gerber's novel Eleanor vs. Ike, Stevenson suffers a fatal heart attack as he approaches the podium to accept the Democratic nomination in 1952. He is replaced as the Democratic presidential candidate by former First Lady Eleanor Roosevelt.
In the alternate history short story "The Impeachment of Adlai Stevenson" by David Gerrold included in the anthology Alternate Presidents, Stevenson is elected in 1952 after Dwight D. Eisenhower makes the mistake of accepting Joseph McCarthy as his running mate instead of Richard Nixon. He successfully runs for re-election in 1956, once again defeating General Eisenhower. However, he proves to be an extremely unpopular president.