I love Reagan but regarding titles I think that gesture goes to Abraham Lincoln.
Abraham Lincoln - Biography of a Failure “Fail forward” toward success
Difficult childhood
Less than one year of formal schooling
1831 - Failed in business
1832 - Defeated for legislature
1833 - Again failed on business
1834 - Elected to legislature
1835 - Fiancee died
1838 - Defeated for Speaker
1840 - Defeated for elector
1842 - Married, wife of burden
Only one of his four sons lived past age 18
1843 - Defeated for Congress
1846 - Elected to Congress
1848 - Defeated for Congress
1855 - Defeated for Senate
1856 - Defeated for Vice-President
1858 - Defeated for Senate
1860 - Elected President
That dastardly site snopes.com took issue with 1840. I wrote to them and told them it was true. He was indeed on the 1840 slate of Whig electors, and the Democrats carried Illinois that year.
What I don’t know (and as far as I could tell, neither did they), was whether Lincoln’s name actually appeared on the ballot.