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Trivia

To date, using the Governors' Executive Journals housed within the Secretary of State's office, 77 individuals have been identified who have served as Secretary of State for the Commonwealth of Kentucky. (This number does not include Assistant Secretaries of State who have assumed the role of Acting Secretary of State.) Of that number, seven Secretaries are living. They are:

Ken Harper
Bob Babbage
John Y. Brown, III
Trey Grayson
Elaine N. Walker
Alison Lundergan Grimes
Michael G. Adams

The first Secretary of State to be born outside the United States was Harry Toumlin (born in England).
Eight women have held the office of Kentucky Secretary of State:

Emma Guy Cromwell (1924-1928)
Ella Lewis (1928-1932)
Sara W. Mahan (1932-1936)
Thelma Stovall (1956-1960; 1964-1968; 1972-1976)
Lelia Feltner Begley (appointed by Gov. Nunn after the death of her husband, Secretary Elmer Begley) (Sept. 21, 1970-Feb. 2, 1971)
Frances Jones Mills (1980-1984)
Elaine N. Walker (Jan. 29, 2011-Jan. 1, 2012)
Alison Lundergan Grimes (Jan. 2, 2012-present)

The first Secretary of State for the Commonwealth of Kentucky was James Brown. He was appointed by Governor Isaac Shelby on June 5, 1792, "with the advice and consent of the Kentucky Senate."
The office of Secretary of State was appointive until 1896, when Section 91 of the 1891 Kentucky Constitution mandated the Secretary's election "by the qualified voters of the State at the same time the Governor is elected." Section 95 required the first election under the 1891 Constitution to be held on the first Tuesday after the first Monday in November 1895. Earlier versions of the Kentucky Constitution allowed the Governor to appoint the Secretary of State "with the advice and consent of the Kentucky Senate.")
Pursuant to Section 91 of the Kentucky Constitution of 1891, the Secretary of State "shall be at least 30 years of age at the time of his election and shall have been a resident citizen of the State at least two years next before his election."
The first Secretary of State elected "by the qualified voters of this state" was Charles Finley. He served from January 1896 to January 1900.
Pursuant to Section 93 of the Kentucky Constitution, Elected Constitutional State Officers, including the Secretary of State are "ineligible to reelection for the succeeding four years after the expiration of any second consecutive term for which they shall have been elected."
The first Secretary of State to hold two consecutive elected terms, under the terms of the 1992 amendment to the 1891 Kentucky Constitution, was John Y. Brown, III (1996-2000; 2000-2004).
From 1792 to 1896, 49 individuals were appointed to the office of Kentucky Secretary of State. Since 1896, 23 individuals have been elected and 3 individuals have been appointed to the office.
From 1792 to 1892, when the Secretary of State was appointed:

During the 1832-1836 gubernatorial term, four different appointees held hte office of Secretary of State;
During eight gubernatorial terms (1804-1808; 1816-1820; 1828-1832; 1844-1848; 1848-1850; 1851-1855; 1859-1863 and 1871-1875), the office was held by three different appointees;
During eight gubernatorial terms (1796-1800; 1808-1812; 1812-1816; 1820-1824; 1824-1828; 1863-1867; 1879-1883 and 1887-1891), two individuals were appointed to serve as Secretary of State;
During the remaining ten guberatorial terms, one appointee held the office.

Since 1896, during which time Secretaries of State have been elected:

One Secretary, Thelma Loyace Hawkins Stovall, has served three separate terms in office (1956-1960; 1964-1968 and 1971-1975);
Three Secretaries have been appointed by the Governor:

Leila Feltner Begley (1970-1971)
Kenneth F. Harper (1971-1972)
Elaine N. Walker (2011)

One Secretary of State, Elmer Begley, died while in office;
One Secretary of State, Trey Grayson, resigned from the office
Three Secretaries have held two non-consecutive terms:

George Glenn Hatcher (1940-1944; 1948-1952)
Charles K. O'Connell (1944-1948; 1952-1956)
Drexell R. Davis (1976-1980; 1984-1988)

Three Secretaries have held two consecutive terms:

John Y. Brown, III (1996-2000; 2000-2004)
Trey Grayson (2004-2008; 2008-2011)
Alison Lundergan Grimes (2012-2016; 2016-2020)

Since 1792, ten Secretaries of State have served multiple terms in office:

Harry Toulmin (appointed for two terms)
Samuel B. Churchill (appointed for two terms)
J. Stoddard Johnston, Sr. (appointed for one term, plus one month of a second term)
John W. Headley (appointed for one term, plus part of a second term due to the Jan. 1896 inaugural date as mandated by the 1891 Kentucky Constitution)
George Glenn Hatcher (elected for two terms)
Charles K. O'Connell (elected for two terms)
Thelma Loyace Hawkins Stovall (elected for three terms)
Drexell R. David (elected for two terms)
John Y. Brown, III (elected for two consecutive terms)
Trey Grayson (elected for two consecutive terms)

The first Secretary of State to be appointed for two consecutive terms was Harry Toulmin (1792-1796; 1796-1800)
The first Secretary of State to be elected for two non-consecutive terms was George Glenn Hatcher (1940-1944; 1948-1952)
Secretary of State Caleb Powers was indicted, incarcerated and later pardoned for his alleged involvement in the assassination of Gov. William Goebel in 1900. (The complete text of Governor William S. Taylor's pardon of Secretary Powers is included on the Timeline page.)
Two Secretaries of State have later been elected Kentucky Governor:

William Owsley (Governor 1844-1848)
John J. Crittenden (Governor 1848-1850; resigned to become U.S. Attorney General)

Two Secretaries of State have served as Kentucky Attorney General:

James Harlan (Attorney General 1850-1859)
Andrew Jackson James (elected Attorney General in 1859)

One former Governor, Christopher Greenup, was appointed to the office of Secretary of State upon the resignation of Secretary Martin D. Hardin. Greenup served from Feb. 3, 1813, to March 11, 1813, during Governor Isaac Shelby's second administration.