"I have always said you would be the greatest President, bar only Washington and Lincoln, and I feel mighty inclined to strike out the exceptions! My affection and respect for you are increased by your attitude about [campaign] contributions. But really I think you are oversensitive."

-- President Theodore Roosevelt, to his friend and handpicked successor, William Howard Taft, in a letter written on August 7, 1908, just a couple of weeks after Taft accepted the Republican Presidential nomination.

President Roosevelt thought Taft -- who was determined to publicly identify all major financial contributors to his campaign and reticent about accepting large amounts of money from certain donors -- was being overly sensitive when it came to what Roosevelt considered the necessary evil of campaign fundraising.

Despite personally selecting Taft to succeed him when he decided not to run for another term in 1908, Theodore Roosevelt quickly grew disappointed with the Taft Administration (and hungry to once again be President). In 1912, Roosevelt challenged Taft for the Republican nomination and, when he didn't receive it, bolted the party to become the nominee of the Progressive or "Bull Moose" Party. The once close friends engaged in a nasty campaign with President Taft suggesting that Roosevelt was no longer fit for office while Roosevelt responded by saying that "Mr. Taft never discovered that I was dangerous to the people until I discovered he was useless to the people." On the campaign trail, Roosevelt not only denigrated Taft's Presidency but resorted to calling his former friend names like "a fathead...with the brains of a guinea pig," which devastated the President -- with a journalist at one point reportedly finding Taft in tears.

With Roosevelt and Taft attacking each other and splitting the votes of Republicans, the Democratic Presidential nominee, Governor Woodrow Wilson of New Jersey, coasted to victory. In 1918, Roosevelt and Taft ran into each other at the restaurant inside Chicago's Blackstone Hotel, and quickly reconciled. When Roosevelt died just a few months later Taft was asked by Roosevelt's son, Archie, to sit with the Roosevelt family near the front of the church during the funeral service. And as Roosevelt's casket was being laid to rest in the snowy Long Island cemetery, Taft was again seen quietly crying.

In July 1921, just a few days after becoming the only former President to also serve as Chief Justice of the United States (which he called "the greatest day of my life"), William Howard Taft wrote to Roosevelt's sister, Bamie: