The first historical anomaly is that Donald Trump is attempting to be only the second former president ever to win a non-consecutive term of office.
After losing his 1840 presidential reelection bid to William Henry Harrison, former President Martin Van Buren lost Democratic nomination in 1844 and later lost as presidential nominee on the on the Free-Soil Party ticket.
Having succeeded to White House upon the death of President Zachary Taylor 1850 and then failing in 1852 to secure his Whig Party's nomination, the execrable 13th President, Millard Fillmore, failed in his 1856 comeback bid as the standard bearer of the aptly named Know Nothings.
After having won two consecutive terms from 1869-1877, former President Ulysses S. Grant sought a non-consecutive third term in 1880 but lost the GOP nomination to James A. Garfield.
The largest obstacle Grant faced was his party and the public's opposition to a president breaking Washington's precedent by serving more than two terms of office.
Finally, eight years following his landslide defeat to FDR, former President Herbert Hoover subtly maneuvered for a rematch but did not obtain the GOP's 1940 presidential nomination.
The first president to accomplish a non-consecutive term of office was our 22nd and 25th president, Grover Cleveland.
Finally, in the rubber match between two presidents, Cleveland again won both the popular vote and, this time, the electoral college, making him the first president to win non-consecutive terms and Harrison the first incumbent GOP president to lose a reelection bid.
Further evincing the difficulty of a former president winning his party's nomination is that there have been incumbent presidents who have failed to receive their party's nomination for a second consecutive term.
Initially elected president in his own right in 1852, four miserable years later Franklin Pierce lost the 1856 Democrat Party nomination.
Further increasing former President Trump and his supporter's uphill struggle, there is one key distinction to be made between the non-consecutive bids of the two New Yorkers, former Presidents Cleveland and Trump: due to a split within his opponents ranks, in all three of his presidential campaigns, Mr. Cleveland won the popular vote; due to a split within his own party's ranks, in two presidential elections, Mr. Trump has never won the popular vote.
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