Sherman was born in Hyannis, Massachusetts, the son of artist Donald Sherman and Diane Sullivan Sherman, the sister of Mary Sullivan who was believed to be the final victim of the Boston Strangler. Sherman attended Barnstable High School and graduated from Fryeburg Academy in 1988. He received a Bachelor of Science degree from Boston University in 1993. As a television news producer for WBZ-TV Sherman led a high profile re-investigation of his aunt Mary Sullivan's murder which he later chronicled in his 2003 book, A Rose for Mary: The Hunt for the Real Boston Strangler. Sherman followed with four more books, Black Irish, Black Dragon, The Finest Hours (co-authored by Michael Tougias) and Bad Blood: Freedom and Death in the White Mountains.

Sherman has been nominated for an Emmy Award, gave the keynote address at the United States Coast Guard's 2009 Prayer Breakfast in Washington, DC and was awarded the 2010 Truth & Justice Award from the prestigious Cold Case Investigative Research Institute.His book, The Finest Hours was a finalist for Massachusetts Book of the Year honors in 2010. Sherman's Bad Blood was optioned for a major motion picture by Moody Street Pictures in 2010. Sherman is also a contributing writer for Boston Magazine, Boston Common, The Huffington Post, and the Open Case.com.

A Rose for Mary: The Hunt for the Real Boston StranglerPublished in 2003, the book chronicled Sherman's 15-year reinvestigation of the murder of his aunt Mary Sullivan, believed to be the youngest and final victim of the Boston Strangler. the 19-year old Sullivan was found strangled with three ligatures in her apartment at 44-A Charles Street, Boston on January 4, 1964. Sherman worked with a team that included forensic scientist James Starrs, famed pathologist Michael Baden and high profile attorneys Dan & Elaine Whitfield-Sharp to prove alleged killer Albert DeSalvo was not in fact the notorious Boston Strangler. By uncovering DeSalvo's long lost confession tape which disputed the actual facts of the case and through DNA testing on Mary Sullivan and the brother of Albert DeSalvo, the team announced their startling findings to the world during a press conference at George Washington University in 2001. Despite the team's findings, the murder of Mary Sullivan still remains an open case with the Massachusetts Attorney General's Office. Sherman claims to have found the lead suspect in Mary Sullivan's murder and confronted the man with the evidence. The episode is described in Sherman's Book. A Rose for Mary received critical acclaim upon its release. Mystic River author Dennis Lehane called it a model of investigative reporting. Booklist called it a must read for true crime aficiondos. A Rose for Mary was later replublished in mass market paperback under the title Search for the Strangler.

The Finest Hours: The True Story Behind the US Coast Guard's Most Daring RescuePublished by Scribner in 2009, and co-authored by Michael J. Tougias, the best-selling book centers on the improbable rescue of 70 seamen left stranded after two oil tankers split in half during a deadly winter nor'easter on February 18, 1952 in the waters off Cape Cod. The main characters, Coasties Bernard C. Webber, Ervin Maske, Richard Livesey and Andy Fitzgerald were given a virtual suicide mission as they were ordered to take a 36-foot wooden lifeboat CG36500 into 70-foot seas in an effort to 33 men on the sinking stern of the S.S. Pendleton. The crew managed to save 32 men on a boat that was designed to carry only 12. Coast Guard crews from across the northeast helped save 38 more sailors from the other sinking oil tanker, the S.S. Fort Mercer . The operation was called the greatest small boat rescue in Coast Guard history. Webber and his crew were awarded the prestigious Gold Life Saving medal for their bravery on that fateful night. The Finest Hours was a finalist for Massachusetts Book of the Year honors in 2009. The Providence Journal called The Finest Hours a blockbuster. The Minneapolis Star Tribune said the book captured the wit, grit and sacrifice of Coasties and their boats.

Bad Blood: Freedom and Death in the White MountainsPublished by UPNE in 2009, Bad Blood tells the true story of a deadly police shooting in Franconia, New Hampshire involving the cousin of Olympic Gold Medalist Bode Miller. On May 11, 2007, 24-year old Liko Kenney shot and killed Franconia police officer Bruce McKay during what was first described as a routine traffic stop. Kenney was then shot and killed by a passerby, ex-Marine Greg Floyd with McKay's gun. Bad Blood examines the heated feud between Kenney and McKay during the years leading up to the shooting and the controversial role Greg Floyd played in the drama. Bad Blood received a starred review from Publisher's Weekly upon its release. The book rights were purchased by Moody Street Pictures and will be developed into a major motion picture by director John Stimpson and producer Dorothy Aufiero.