The New York Times has put up a cool web-page that show's who they've endorsed in every presidential election since they endorsed Abraham Lincoln in 1860.
It's lots of fun to play with. In the past 38 presidential elections the NYT has supported Democrats 26 times (well, make that 25, because in 1896 they supported John Palmer of the National Democratic Party). Back in the 19th century they endorsed illustrious Republicans such as Abraham Lincoln and Ulysses S. Grant; in the 20th century they also went for a famous (lite) Republican General-War-Hero-turned-politician, Dwight Eisenhower. Since Eisenhower, however, they've never found a Republican they could like. Moreover, the last two times they did endorse Republicans, their choices were a bit odd: Wendell Willkie, in 1940? Huh? Thomas Dewey in 1948: heh heh. And they were against Theodore Roosevelt, back in 1904.
So looking back, how good has the NYT been at choosing fine presidents? Mediocre, I'd say. In spite of them being The Grey Lady.