The public was attracted to both Theodore Roosevelt (in 1912) and Ross Perot (in 1992) because they were fiery, spirited men who challenged the status quo of politics. In both elections, running as 3rd party candidates, these men divided the votes of the Republican party, and thus both elections were won by Democratic party candidates.
In the 1912 election, the Republican Party was divided. Its conservative wing supported President William Howard Taft for reelection. Theodore ("Teddy") Roosevelt, who had been President from 1901-1909, led the progressive wing of the Republicans. Ultimately, Roosevelt and his supporters objected to the nomination of Taft as the Republican candidate, and formed a 3rd party, the Progressive Party, with Roosevelt as their presidential candidate. Roosevelt won 27% of the popular vote; Taft received 23% of the popular vote. Democratic candidate Woodrow Wilson got 42% of the popular vote and carried 40 states to win the Electoral College vote handily.
In the 1992 election, Texas businessman Ross Perot painted himself as the non-political candidate and financed most of his own campaign with his own funds. He pledged to balance the government budget and enact policies that protected American businesses. Famously, he opposed the North American Free Trade Agreement, saying it would result in "a giant sucking sound" of American jobs heading south to Mexico. Though not officially a breakaway from the Republican Party, most of the votes Perot drew to himself came from the Republican side. In the 1992 election, incumbent Republican President George W. Bush got 37% of the popular vote, and Perot got 19%. The Democratic candidate, Bill Clinton, received 43% of the popular vote and carried 32 states to win the Electoral College victory with 370 electoral votes.