1909 cartoon: TR hands his policies to the care of Taft while William Loeb Jr. carries the "Big Stick"
When Theodore Roosevelt became Governor of New York he was appointed as one of his official stenographers.[3] His ability to do things without specific instructions and his familiarity with public officials and affairs attracted Roosevelt's notice and Loeb became his private secretary in 1899.
In the White House he served as assistant secretary to the President from 1901 to 1903, and then succeeded George B. Cortelyou as Secretary to the President in 1903[5] where he stayed by the President's side for the rest of Roosevelt's time in office.
Loeb was a very intimate aide to Roosevelt and was one of the era's most powerful figures. As Roosevelt's principal advisor he participated in shaping policy and solving political problems. Acting as the President's public alter-ego, he unofficially became the nation's first presidential press secretary, as Loeb was empowered to speak for the President and reporters were able to contact him twenty-four hours a day.[6] Known to those in the press as "Stonewall Loeb",[3] he controlled access to the President in an unprecedented fashion, dealing with the queries of most of the President's visitors without their ever having to disturb him.
Roosevelt once described him as "The best secretary that any President ever had". In addition, in his own autobiography, Roosevelt stated that Loeb was responsible for starting the investigations into the frauds committed by the Sugar Trust in New York's Custom House.[9]
He also played a part in aligning the 1908 Republican National Convention behind the nomination of William H. Taft. In January 1908 he brought it to the President's attention that there was no front-runner for the Republican nomination to succeed him and that many Republican leaders in the United States Congress were under the suspicion that Roosevelt had every intention of running for a third term. Loeb urged the President that he would only be able to sustain the credibility of his pledge not to run again by endorsing a candidate. Loeb told Roosevelt that any nominee could win if only he would back him. In response, Roosevelt said that he would favor Elihu Root and authorized Loeb at that moment to go to see Root and make the offer of his endorsement. Root, then Secretary of State, was astonished by the endorsement but did not accept it because he judged himself to be unelectable. Loeb reported back to the President that same day to report on his meeting. Roosevelt accepted Root's decision and told Loeb that his choice then was William Howard Taft, saying that he had the experience to run the government.[10]
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