The last time the New York Times endorsed a Republican for President was never.I think they were sad that Stalin never emigrated to the US so they could endorse him during the height of the forties when a certain number of their readers were commie sympathizers along with some of their staff like Walter Duranty. Their failure can come no too soon
Having grown up in New York I was confident it hadn’t happened in my 50-year lifetime, but I checked and the last Republican endorsed by the New York Times was Dwight Eisenhower, twice, and before that, Thomas Dewey (the latter was a New Yorker so it figured.)