OK, I’ll take a shot at this. It’s more fun than work.
My Ground Rules—my decisions will be made based only on what was known at the time of each election. In some cases, which I’ll note, I would have voted one way and had buyer’s remorse afterward. Also my choices will be restricted to candidates who carried at least one state, so splinter abolitionist and libertarian parties are out.
My Ideology—I believe the function of government is to protect the life, liberty, and property of its inhabitants. In almost all cases this will mean I support the candidate advocating lower taxes and a smaller and less intrusive federal government. If you disagree with this ideology, then you’ll disagree with most of my choices.
However, because of the complication of slavery and Jim Crow, we had a federal government for much of American history which abdicated its core responsibility of protection, and in certain cases needed to be more expensive and intrusive. These cases will be noted as appropriate. Note that before 1844 slavery played little role in presidential politics, nor did civil rights between roughly 1880 and 1960, so these issues play little or no role in my choices for those years.
I favor a foreign policy of non-intervention except where America is attacked or under clear and present danger of an unprovoked attack. This sometimes makes choices difficult because often candidates who hold the line on domestic spending never met a war they didn’t like. And vice versa.
1796-Jefferson over Adams
1800-Jefferson over Adams, once more with feeling, after Adams disgraced himself with the Alien & Sedition Acts
1804-Jefferson over King; subsequent buyer’s remorse after the insane Embargo of 1807
1808-Madison over Pinckney
1812-Clinton over Madison; the only thing worse than starting an unnecessary war is starting an unnecessary war after a criminal lack of preparation
1816-Monroe over King
1820-no contest
1824-Adams over Jackson; Adams favored a modestly more intrusive government, but Jackson loses on authoritarian personality and disgraceful advocacy of Indian removal. Also, Jackson was an economic illiterate.
1828-Adams over Jackson
1832-Clay over Jackson
1836-Harrison over Van Buren
1840-Harrison over Van Buren; tough call in a content-free campaign
1844-Clay over Polk and avoid the Mexican War
1848-Cass over Taylor; non-buyer’s surprise after Taylor turned out to be anti-slavery, but then died and was succeeded by doughface Fillmore
1852-Scott over Pierce; no more doughfaces!
1856-Fremont over Buchanan and Fillmore
1860-Lincoln over Douglas, Breckinridge, and Bell
1864-Lincoln over McClellan
1868-Grant over Seymour
1872-Grant over Greeley; definite buyer’s remorse as Grant abandoned Reconstruction during his second term and imploded in scandal
1876-Hayes over Tilden; more buyer’s remorse as Hayes abandoned what was left of Reconstruction
1880-Garfield over Hancock; Garfield actually might have been a good president
1884-Cleveland over Blaine; with Reconstruction over, Cleveland gets the nod as a tiger on spending
1888-Cleveland over Harrison
1892-Cleveland over Harrison
1896-McKinley over Bryan
1900-McKinley over Bryan
1904-Parker over Roosevelt
1908-Taft over Bryan
1912-Taft over Roosevelt and Wilson; boy would I have been pissed on Election Night as Taft got crushed by two of my least favorite presidents
1916-Hughes over Wilson
1920-Harding over Cox
1924-Coolidge over Davis and LaFollette
1928-Smith over Hoover; Smith was arguably more of an economic conservative than Hoover, and at least he was a wet
1932-Roosevelt over Hoover; Hoover ruled himself out by signing tax increases and the Smoot-Hawley tariff in the middle of a Depression and trampled civil liberty by stomping the bonus marchers. Roosevelt, believe it or not, campaigned as a conservative.
1936-Landon over Roosevelt
1940-Willkie over Roosevelt
1944-Dewey over Roosevelt
1948-Dewey over Truman
1952-Eisenhower over Stevenson
1956-Eisenhower over Stevenson
1960-Kennedy over Nixon; Kennedy’s deification by liberals occurred after his death; in life he was very much a centrist and campaigned on tax cuts, and well Nixon was Nixon.
1964-Goldwater over Johnson
1968-Nixon over Humphrey in a nose-holder
1972-McGovern over Nixon; McGovern was an ultra-liberal and anathema to everything I believe, but Nixon had grown domestic spending faster than any Democrat, signed wage and price controls (gag), and treated civil liberties like a dishrag. At least McGovern was honest, and Congress might have restrained his worst spending impulses.
1976-Ford over Carter
1980-Reagan over Carter
1984-Reagan over Mondale
1988-Bush over Dukakis
1992-Bush over Clinton
1996-Dole over Clinton
2000-Bush over Gore
2004-Bush over Kerry but a much tougher call after Bush grew spending, expanded entitlements, and started a hugely expensive and unnecessary war
2008-McCain over Obama