Alf Landon ran against Franklin Roosevelt in 1936. Roosevelt was already in office "giving America a chance," something which Landon had no hope of in this race.
Landon, a World War I officer, was a petroleum millionaire and governor of Kansas. He was, in fact, the only Republican governor re-elected in 1934. He fought off an attack by Herbert Hoover in the primary season and won the GOP nomination on the first ballot at convention.
Landon, however, was a lousy campaigner. He seldom traveled, appearing nowhere in the first two months after his nomination. Most of his campaign was developed by others. It seems the Kansan liked Roosevelt and much of his New Deal, but argued against too much waste and found it to be bad for businesses. Late ad hominem attacks didn't help either as Landon lost the general election by more than 10 million votes, carrying only Maine and Vermont, losing even his own Kansas.
Langdon served out his gubernatorial term, returned to the oil fields and never ran for office again, though he did help salve party wounds in the late 1930s. He died (as the earliest born governor still living) in 1987 a month after his 100th birthday.
Also on that pin is Frank Knox, a newspaper reporter and publisher. He would go on to fight with the Rough Riders in the Spanish American War, the vice presidential candidate for the Republicans and served as Roosevelt's Secretary of the Navy from 1940 until his death in 1944.
Without delving too much into the politics of either, here's a great old clip from that 1936 race when presidential candidates, for the first time, could be seen on television (in very limited capacity).