Sherman was born on February 16, 1953, in Robertsport, Grand Cape Mount County and graduated from St. John's Episcopal High School in 1971. He continued his education at Cuttington University where he earned a degree in 1975. In 1979, he was awarded a Bachelor of Laws at the Louis Arthur Grimes School of Law at the University of Liberia in Monrovia. Sherman completed his education in 1982 in the United States where he earned a Master of Law at Harvard Law School.
By 1997, in the aftermath of the First Liberian Civil War, Sherman had begun to speak prominently on political matters. A prominent Monrovia lawyer and a partner in the law firm of Sherman and Sherman, he garnered front-page newspaper coverage for a speech to the Liberian Business Association denouncing the government for what he saw as non-enforcement of a hiring policy meant to favor Liberian citizens and businesses. Running as the standard bearer of the four-party Coalition for the Transformation of Liberia (COTOL) in the 11 October 2005 presidential elections, Sherman placed fifth out of 22 candidates, receiving 7.8% of the vote. He then endorsed George Weah for the run-off election.
Following the merger of his Liberian Action Party into the Unity Party in 2009, Sherman was chosen to become the national chairman of the party.
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