I would say that Cleveland’s 1884 Campaign was quite sub par, but it still won. He did nothing for damage control on the Illegitimate Child Scandal (except fess up to it) and he was going to lose New York, the state hen governed, if not for the “rum, Romanism, and rebellion” gaffe by the Blaine Campaign. Had Blaine ran a slightly better race in 1884, Cleveland would have lost.
Taft in 1908 was another great example. His campaign was lacking energy and organization, which Bryan had. Bryan was simply his own worse enemy. He tracked down the road to Socialism, thus the sub par Taft Campaign could win in 1908. Bryan had a better campaign machine by far, and thus he nearly won the election. A 5-10% shift in several Middle West and Western states would have secured Bryan a win. Taft, with the backing of the popular President Teddy Roosevelt, should have easily won.
Warren G. Harding’s 1920 Campaign was also not that great. His “return to normalcy” campaign was just a platitude. Had the Democrats not been in such disarray in 1920, the intelligent Governor Cox would have won in 1920. How would we respond to a president name “Cox” however?
Actually, If I recall one of my books correctly, it seemed as though the country was indeed ready to accept Bryan, as he had tempered his silver views, and many were considering him... He even began a debate by mail with Theodore Roosevelt.
However, one speech... Just one... wrecked his chances forever. He mentioned advocating government ownership of railroads (Which today, we don't even flinch at it). At the time it was downright socialist to say that and his campaign was destroyed...