Early Progressive Leader
In 1900 he threw his support and substantial financial backing behind Robert M. La Follette, Sr., in his campaign for the Wisconsin governorship, and for a number of years was a prominent adviser to the Progressive faction of the Republican party, and a liberal contributor to its campaign funds. In the 1904 progressive-stalwart split, Stephenson was chosen by the "gymnasium convention" as one of the progressive delegates to the Republican national convention along with La Follette and William D. Connor. Although the national convention refused to accept the credentials of the Progressive delegation, the La Follette forces were recognized as the legal Republican ticket by the Wisconsin Supreme Court (1904).
In 1901 Stephenson established the Milwaukee Free Press, providing Progressive-Republicans with a metropolitan newspaper, and competition for the Stalwart-controlled Milwaukee Sentinel. In 1907 Stephenson sought the U.S. Senate seat made vacant by the resignation of John C. Spooner and, after a brief deadlock, was elected by the Progressive-controlled state legislature. In 1908 he ran for renomination in the Republican primary, was opposed by La Follette, but despite this opposition won the nomination through the aid of the state chairman of the Republican party William D. Connor and lavish use of his personal wealth, and was re-elected by the legislature in 1909. Although his election was twice blocked by fraud investigations in both the state legislature and the U.S. Senate, Stephenson was eventually vindicated and resumed his seat in the Senate, serving from May 1907, to March 1915.
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