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Truman could have run again in 1952 (the 22nd amendment did not apply to him) but he was very unpopular because of the stalemate in the Korean War and didn’t run. Wilson would have run for a third term in 1920 but the party wouldn’t hear of it (this was after his stroke). To be sure that’s more than 100 years ago.

True, but Truman had served almost eight years. And if Truman had run, it would have been much tougher on Eisenhower. One huge difference is that was that had been five Democrats terms in a row. It's hard to keep building on that.

Their is no way Wilson could have run in 1920, given his health. He was bedridden, and not completely there mentally, and it came out in early 1920. It would basically been Edith running.

The one you left out is Calvin Coolidge. He could have easily won in 1928, but he spent ten years in D.C. and was sick of it. I don't think any president of the media era would give up power that easily, except maybe Reagan.