1984- Reagan
1988- Bush
1992- Clinton
1996- Clinton
2000- Bush (Missed this one, and we all know how close it was.)
2004- Bush
2008- Obama
2012- Obama
2016- Trump
2020- Biden
On the closer races, 2004, 2016, and 2020, he picked the candidate who had the better chance of winning and/or had momentum near the end. The rest were forgone conclusions well before election day.
"If you will not fight for right when you can easily win without blood shed; if you will not fight when your victory is sure and not too costly; you may come to the moment when you will have to fight with all the odds against you and only a precarious chance of survival. There may even be a worse case. You may have to fight when there is no hope of victory, because it is better to perish than to live as slaves." - Sir Winston Churchill