Toby Gilmore

Early life

Around 1758, Shibodee Turrey Wurry was captured by slave traders while collecting coconuts, and placed in chains below deck aboard the slave ship Dove. This ship bound for Virginia had to change course because it was damaged during a storm, sailing to Rhode Island instead. There he was auctioned off and purchased by Captain (nautical, not military) John Gilmore of Raynham Massachusetts. According to local legend John and his wife had no children of their own and renamed Shibodee to Toby Gilmore, teaching him to read and write. However this has proven to be untrue; the couple had several children, and it is unclear if Toby could read and write.

Revolutionary War

During the war, Toby was attached to military companies that served at Battle of Monmouth, Battle of Forts Clinton and Montgomery, Battle of White Plains, West Point, Siege of Fort Ticonderoga (1777) and the Winter at Valley Forge.

Toby began his service on December 8, 1776, as a Private in Capt. Jonathan Shaw’s company, Col. George Williams’s Regt. (3rd Bristol Co.) He served for eleven days. The company marched to Warren, RI, on an alarm. November 4, 1777, he joined Capt. James Cooper’s company, Col. Gamaliel Bradfords’s 12th Regt. After that his Continental Army pay records show he served from September 19, 1777, to September 3, 1780; he was enlisted for three years. In 1781 he served for two months and 24 days at North River (Hudson River). He was discharged from the army in December 1781 and returned home to Raynham. Afterwards he served during Shays' Rebellion his mitre was embroider with the a Federalist logo. Some of the records for him are missing local history/legend has linked him with Gen. George Washington

Lore of George Washington

It is unknown whether or not Gilmore served under Gen. Washington. Local history of the Greater Taunton area states that Toby during the war rose in the ranks to the position of “body guard “ or “body servant” of George Washington. For his service he was awarded a cannon, that today resides at Old Colony Historical Society (OCHS) in Taunton, Massachusetts nicknamed “Old Toby“. Every July 4 in celebration Toby would fire the cannon 14 times; 13 of these shots fired for the original Thirteen Colonies and the last shot would be fired to honor Gen. Washington. Some have made claims that Toby is the African American pictured in the 1851 oil painting Washington Crossing the Delaware. Popular belief today is that the figure was Prince Whipple; however, it is documented that Whipple and his master were in Baltimore at the time of the crossing. It is more likely that Emanuel Gottlieb Leutze the painter wanted to express that black patriots fought alongside their white counterparts during the Revolutionary War. The image of the black soldier in the painting is not of anyone in particular but embodies all Black Patriots.

Freedom after the war

By the end of his service Toby was married to Rosanna Hack. They would go on to have eight children: Toby Jr., Nancy, Delia, Timothy, Esquire, Selina, Rosina, and Seabury. Toby returned and worked for his former master. Later he and his wife started their own housekeeping business. Toby was considered to be a frugal businessman and purchased forty-five acres and sixty rods of confiscated land in Raynham, Mass. The land was confiscated from a loyalist and auctioned off. Toby was so well liked in the area that very few prospectors bid against him.

The first house he built about 1784 still stands in Raynham. In 1798 he built his second homestead that was larger than his former master's home.

Toby died April 19, 1812, at the age of 70, according to his grave marker that still stands at Hall & Dean Cemetery in West Raynham.

Old Colony Historical Society

Most of the history of Toby Gilmore can be found at OCHS where local historians are the keepers of some of his artifacts. These artifacts include his military mitre, “Old Toby” the canon, and his rundlet all on display. In the archives they have a military coat that was also donated by the Gilmore family. It is unclear exactly what period the coat comes from but it is unlikely that it was Toby’s. It is speculated that it comes from one of his descendants and is a Civil War era coat.

The Taunton Daily Gazette on October 24, 1921, did a short article stating that Caroline J. Gilmore, the last member of the Gilmore line, had died that morning. It was believed that all of Toby’s Gilmore descendants had died out. In the summer of 2010 OCHS staff along with one of the Gilmore descendants rediscovered the missing genealogical link. The article was printed on October 20, 2010 in the Taunton Daily Gazette.