Under the second Constitution for the period from 1821 to 1846, Sheriffs were elected to a term of three years and ineligible to election the next succeeding term.
The first Sheriff of Chenango County was Uri Tracy of Oxford, NY
appointed March 22, 1798.
Following the first Sheriff were;
Nathaniel Locke appointed August 12, 1801
Anson Carey appointed March 1, 1805
William Monroe appointed March 23,1809
Isaac Foote Jr. appointed April 5, 1810
William Monroe appointed February 8, 1811
Isaac Foote Jr. appointed February 26, 1812
Samuel Campbell appointed March 6, 1815
William Monroe appointed March 6, 1819
Thomas Meade appointed February 12, 1821
Thomas Meade was elected in 1822 and succeeding him the following years were:
Samuel Smith - 1825
Augustus Welch- 1828
Amos Franklin - 1831
Jabez Robinson - 1834
William Hatch - 1837
Enos Halbert - 1840
Joseph P. Chamberlin - 1843
William Church - 1846
Levi Case - 1849
Romeo Warren - 1852
William H. Ormsby - 1855
Peter Rathbone - 1858
Edward Childs - 1861
Daniel A. Carpenter - 1864
John F. Mathewson - 1867
Uriah Rorapauch - 1870
William M. Brown - 1873
Silas R. Hill - 1876
Alvin C. Hazard - 1879
Ira W. June - 1882
John Robb - 1885
Alonzo S. Kinney - 1888
Edward A. Lally - 1891
George W. Payne - 1894
Zenas Tarbell - 1897
James J. Flanagan - 1900
George L. Page - 1903
William Beardsley - 1906
Harmon Walworth - 1909
Charles S. Holcomb - 1912
Neil Lewis - 1915
H. Fred Hovey - 1918
Leon Walworth - 1921
Neil Lewis - 1924
Rex Ormsby - 1927
Neil Lewis - 1930
Charles Dunckel - 1933
Neil Lewis - 1936-1939
Leland Brookins - 1942-1945
Frank Machio - 1948-1960
(Resigned in mid-term)
Joseph J. Benenati Jr. - 1960
(appointed to fill unexpired term in august)
Joseph J. Benenati Jr. - 1961-1981
Morris "Moe" Eccleston - 1982
Thomas J. Loughren - 1992-6/2009
Ernest R. Cutting Jr. - 6/2009 - Current