List of Sheriffs Of Worcester County, Massachusetts (28 items)report

• [#]: 1st
  [Sheriff]: Daniel Gookin
  [Picture]:
  [Term]: June 30, 1731 - June 1743
  [Party]:
  [Note]:
  

• [#]: 2nd
  [Sheriff]: Benjamin Flagg
  [Picture]:
  [Term]: 1743–1751
  [Party]:
  [Note]:
  

• [#]: 3rd
  [Sheriff]: John Chandler
  [Picture]:
  [Term]: 1751-August 7, 1762
  [Party]:
  [Note]:
  

• [#]: 4th
  [Sheriff]: Gardner Chandler
  [Picture]:
  [Term]: 1762–1775
  [Party]:
  [Note]: Last Worcester County sheriff of the royal Province of Massachusetts Bay.
  

• [#]: 5th
  [Sheriff]: Simon Dwight
  [Picture]:
  [Term]: 1775–1778
  [Party]:
  [Note]:
  

• [#]: 6th
  [Sheriff]: William Greenleaf
  [Picture]:
  [Term]: 1778–1788
  [Party]:
  [Note]: Impeached and removed for misconduct.
  

• [#]: 7th
  [Sheriff]: John Sprague
  [Picture]:
  [Term]: 1788–1792
  [Party]:
  [Note]:
  

• [#]: 8th
  [Sheriff]: Dwight Foster
  [Picture]:
  [Term]: 1792–1793
  [Party]: Federalist
  [Note]:
  

• [#]: 9th
  [Sheriff]: William Caldwell
  [Picture]:
  [Term]: 1793–1805
  [Party]:
  [Note]:
  

• [#]: 10th
  [Sheriff]: Thomas Walker Ward
  [Picture]:
  [Term]: 1805–1824
  [Party]:
  [Note]:
  

• [#]: 11th
  [Sheriff]: Calvin Willard
  [Picture]:
  [Term]: 1824–1844
  [Party]:
  [Note]: Resigned rather than hang a condemned prisoner.
  

• [#]: 12th
  [Sheriff]: John W. Lincoln
  [Picture]:
  [Term]: 1844–1851
  [Party]:
  [Note]:
  

• [#]: 13th
  [Sheriff]: James Estabrook
  [Picture]:
  [Term]: 1851–1853
  [Party]: Democratic
  [Note]:
  

• [#]: 14th
  [Sheriff]: George W. Richardson
  [Picture]:
  [Term]: 1854–1856
  [Party]: Know Nothing
  [Note]:
  

• [#]: 15th
  [Sheriff]: John S.C. Knowlton
  [Picture]:
  [Term]: 1857–June 11, 1871
  [Party]: Democratic
  [Note]: First sheriff elected by popular vote. Died in office on June 11, 1871.
  

• [#]: 16th
  [Sheriff]: Augustus B. R. Sprague
  [Picture]:
  [Term]: July 5, 1871-January 1890
  [Party]:
  [Note]: Appointed to fill the vacancycaused by the death of sheriff John S.C. Knowlton who died in office.Subsequently elected for six three year terms.
  
  

• [#]: 17th
  [Sheriff]: Samuel D. Nye
  [Picture]:
  [Term]: 1890–1892
  [Party]: Democratic
  [Note]:
  

• [#]: 18th
  [Sheriff]: Robert H. Chamberlain
  [Picture]:
  [Term]: 1892–January 14, 1910
  [Party]: Republican
  [Note]: Resigned on January 14, 1910.
  

• [#]: 19th
  [Sheriff]: Benjamin D. Dwinnell
  [Picture]:
  [Term]: 1910 – December 15, 1916
  [Party]: Republican
  [Note]: Died on December 15, 1916.
  

• [#]: 20th
  [Sheriff]: Albert F. Richardson
  [Picture]:
  [Term]: December 1916 - March 13, 1932
  [Party]: Republican
  [Note]: Died on March 13, 1932.
  

• [#]: 21st
  [Sheriff]: Henri Oscar Rocheleau
  [Picture]:
  [Term]: March 23, 1932 - January 1945
  [Party]: Democratic
  [Note]: Appointed to the office by Joseph B. Ely to fill the vacancycaused by the death of sheriff Albert F. Richardson.
  

• [#]: 22nd
  [Sheriff]: William A. Bennett
  [Picture]:
  [Term]: January 1945-January 1963
  [Party]: Republican
  [Note]:
  

• [#]: 23rd
  [Sheriff]: Joseph A. Smith
  [Picture]:
  [Term]: January 1963 – 1977
  [Party]: Democratic
  [Note]:
  

• [#]: 24th
  [Sheriff]: Francis J."Bud" Deignan, Jr.
  [Picture]:
  [Term]: January 1977 - 1983
  [Party]: Democratic
  [Note]:
  

• [#]: 25th
  [Sheriff]: Theodore M. Herman
  [Picture]:
  [Term]: January 4, 1983 - 1987
  [Party]: Democratic
  [Note]: Appointed Worcester County Sheriff, to fill vacancy; on January 4, 1983, by Governor Edward J. King. Herman won the 1984 Democratic primary and the subsequent November 1984 election to fill the unexpired term.
  

• [#]: 26th
  [Sheriff]: John M. Flynn
  [Picture]:
  [Term]: 1987–2005
  [Party]: Democratic
  [Note]:
  

• [#]: 27th
  [Sheriff]: Guy Glodis
  [Picture]:
  [Term]: 2005–January 5, 2011
  [Party]: Democratic
  [Note]:
  

• [#]: 28th
  [Sheriff]: Lewis Evangelidis
  [Picture]:
  [Term]: January 5, 2011 –
  [Party]: Republican
  [Note]:
  

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