In 1848, Simon emigrated to the United States, where several of his uncles had already settled. He entered his uncle's business at Uhrichsville, Ohio, but a commercial career did not attract him and he took up the study of law, graduating with honors from Ohio Law College in Cleveland in 1861.
Upon Simon's graduation from Ohio Law College in 1861, he was admitted to the bar in Mount Vernon, Ohio. After practicing law for a year in New Philadelphia, Ohio, he moved to Washington, D.C., where he lived until his death.
In 1869, Wolf was appointed recorder of deeds for the District of Columbia, holding that office until May 1878. From 1878 to 1881, he served as a civil judge. In July 1881, President Garfield appointed him the United States consul general in Egypt, but he resigned in May 1882 because of illness in his family.
In addition to his official duties, Simon gave his time freely to many local philanthropic and cultural institutions, regardless of their sectarian character. An able lecturer, an eloquent speaker and a lover of his fellowmen, he was always at the front of any fight, which involved issues, where human or civic rights were at stake.
In the midst of an active life, Wolf also found time for literary work. In addition to numerous papers and articles for the periodical press, he was the author of "The Influence of the Jews on the Progress of the World" (1888), "The American Jew as Patriot, Soldier and Citizen" (1895), "Mordecai Manuel Noah" (1897), "Presidents I Have Known from 1860 to 1918" (1918), and, in conjunction with Max J. Kohler, "Jewish Disabilities in the Balkan States" (1916).
After his death, the Council of the Union of American Hebrew Congregations published "Selected Addresses and Papers of Simon Wolf" (1926) as a memorial volume.
As an orator, Wolf was in demand for national political campaigns for many years. His reputation, however, rested largely upon his vigorous championship of the civic and religious rights of his persecuted coreligionists, the Jews of eastern Europe, and the influence, which he wielded with the administration in Washington on their behalf.
For more than half a century, Wolf was in close contact with the most influential men in political life and enjoyed the personal acquaintance of every president, beginning with Abraham Lincoln. When the persecution of the Jews of Romania became acute during Grant's administration, he was the leading advocate of the appointment of Benjamin F. Peixotto as consul to Bucharest, with a view to devising plans for ameliorating their condition. He was one of the leading factors in inducing President Roosevelt to forward a petition to Russia after the Kishinev massacre in 1903. His advice was sought during President Taft's administration in connection with the abrogation of the Russian treaty and he interested President Wilson in plans for the protection of the Jewish religious minorities in the peace treaties at the close of the World War.
Wolf was active within the Independent Order B'nai B'rith, which he joined in 1865. For many years he served this organization as a member of the executive committee and was president in 1904-1905. Through his inspiration, the B'nai B'rith raised funds for the presentation of the statue "Religious Liberty", by Moses J. Ezekiel, to Fairmount Park, Philadelphia.
It's important to note, that Simon was the founder of the Hebrew Orphan's Home in Atlanta, Georgia, and its lifelong president. Upon his motion, the Board of Delegates of American Israelites was merged in 1878 with the Union of American Hebrew Congregations, and he was for many years the chairman of the Board of Delegates on Civil Rights of that body. His services were also given to the Order Kesher shel Barzel, to the Red Cross Association and the Masons of the United States - he was a freemason, member of Lafayette lodge, No. 19, of Washington, D.C.
Simon married Caroline (Hahn) Wolf on August 2, 1857. Their marriage produced six children, one of whom, Florence Wolf Gotthold, became a painter. In 1891, Caroline passed away, and, on November 3, 1892, Simon married his second wife - Amy (Lichtenstein) Wolf.