1952Governor Adlai Stevenson (D-IL) / Senator John Sparkman (D-AL)
Businessman John Coolidge (R-CT) / Senator Everett Dirksen (R-IL) ✓
Coolidge would face an uphill battle at first. None of Eisenhower's unique apolitical appeal as a moderate former Democrat and war hero, and extra baggage as a reminder of the conservative Republicanism that led to the Great Depression and contributed to the outbreak of World War II at a time when it still wasn't quite clear that the US was out of the woods yet. I'm guessing he has Eisenhower's blessing and runs as an internationalist, but faces headwinds from Taft's faction. They did say he was pretty charming, to his credit, and he benefits from a Democratic Party in sorry shape. The Shivercrats still net him Texas, the Byrd Organization still gets him Virginia, and Southern Florida businessmen turn out for him.
1956President John Coolidge (R-VT) / Vice President Everett Dirksen (R-IL) ✓
Fmr. Governor Adlai Stevenson (D-IL) / Senator Estes Kefauver (D-TN)
Things go well with the end of the Korean War and a strong economy, until his October Surprise- the unqualified businessman son-of-an-isolationist's handling of the Suez Crisis and Hungarian Uprising would get more scrutiny without the trust that Eisenhower's credentials inspired. The low farm prices and severe drought of the 1950s, which actually affected a larger area than the Dust Bowl albeit less catastrophically with wiser approaches to land management, also reminds the Plains of 1932.
Side note, Coolidge probably moves back to the quiet family estate in Vermont after leaving the Connecticut Manifold Forms Company.