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Submitted By: Otto Coldiron
Sheriffs of Harlan County Kentucky
Written and researched By:
Otto G. Coldiron
1125 Arlanie Road, 
Brooksville, FL  34604-6907 
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Sheriffs Of Harlan County, Kentucky

In researching the Coldiron family for many years, I have been collecting notes on the Sheriffs of Harlan County.  This is partly because some of my relatives have been Sheriff of Harlan County, and also because the office has been an interesting one to study ­ receiving national attention in the 1930's.  I have tried without success to locate a chronological list of these colorful characters but there doesn't seem to be one available.  What follows is an attempt to list them in order in which they served, including historical and genealogical information on each from the notes in my files.  I caution readers that some of the genealogy information has not been verified against original sources.

In Harlan Footprints, Vol 1, No. 2, Dec 1982, page 25, editor Holly Fee included an overview of the office of Sheriff in an article titled Background.  It is included below to give the reader an orientation to the office.

Prior to 1851, the County Court not only filled their own vacancies but appointed other county officials.  The County Clerk, Constables, the Coroner and the Surveyors of the Roads were all life appointments.  The County Attorney served for one year; the Jailer served "at the pleasure of the Court."  Tax Assessors and Collectors were appointed yearly.  The two year term of Sheriff was the most powerful and financially rewarding office in the county.  The County Court was generally bound to recommend to the Governor the most senior of their magistrates for the office of Sheriff until 1851 when the office became an elected position and some of its power was diluted by the office of County Judge.  In financial terms, the office of Sheriff was rewarding as it received commissions for the collecting of taxes, both county and state, and fees for the execution of Judgments, serving of summonses, etc.  There was also good opportunity for illegal profit particularly by the demanding of an additional percentage for the execution of judgments.  On a statewide basis, the office was often sold or leased, wholly or partially.  The Sheriff was also powerful politically as he was the chief election officer in the county and was often involved in local election disputes and sometimes outright fraud.  Indirectly, a Sheriff held great influence over many voters by the simple tactic of using the threat of serving a summons or executing a judgment if the vote was not as he indicated.

Harlan County was established in 1819.  It previously was part of Knox County.

The period each Sheriff served (in parentheses after each name) was obtained primarily from reading the Harlan Co. Court Orders from 1829 to 1950, and from reviewing election results from 1950 to present.  It has been impossible to determine the complete period every Sheriff served ­ those who were in office up to about 1880 are not mentioned frequently in the Court Orders.  When only one year is given, as in (1838), it indicates that a reference was made in the Court Orders identifying the Sheriff at that time.  He could also have been Sheriff slightly before and after that period.  The numbers after the period served refer to the references listed at the end of the article.  Here they are ­ as much as I know about them ­ the Sheriffs of Harlan County.

*Benjamin Horn (1819) 25

He was appointed Sheriff in 1819 by Gov. Gabriel Slaughter when Harlan County was first incorporated.  He was therefore the very first Harlan County Sheriff.

*Benjamin Harris  (ca. 1820's) 1, 2

*John Lewis  (ca. 1820's) 1, 2

*Elisha Green (1829 ­ 1832) 1, 3, 24

He was born 1788 in Russell Co., VA, s/o Lewis Green and Esther Kilgore.  He had 11 children by first wife Nancy Bingham, d/o John A. Bingham and Deborah Phipps.  He and Nancy divorced, after which he married Mary Prudence Brittain.  Elisha died 1860 in Mason Co. KY.

*John Turner (Nov 1832 ­ 1834) 1, 4 

*Luke Noe (1835) 1, 5

*Samuel Howard (1838) 1

*Jack (John) McGeorge, 32 years old (1839) 26

*John Noe (1839 ­ Mar 1840) 1

*James Sparks (1842 ­ 1844) 1, 6

*Moses Cawood (1845 ­ 1848) 1

*Jonathan Kelly (1851) 1, 8

*Zachiariah B. Saylor (1853) 1

*David Bailey (1856) 1

*Jonathan Lewis (1857) 1

*John McGeorge (1859­1860) 1, 24 

John was born 1807/1810, the s/o James McGeorge and Ann LaForce.  John married Letitia Green, d/o James Green and Nancy Arnett, on 31 Aug 1826 in Harlan Co.  James Green was brother to Elisha Green (above).  John is in the 1830, 1840, 1850, & 1860 Harlan Co. census, and in the 1870 & 1880 Bell Co. census.

*Acles Wynn (1861)1

Early spelling of his name was Achilles; spelled Acles in 1860 Harlan County census.  He was the first Wynn to settle in Harlan County, arriving about 1830-1840.  He and his family lived on Yokum Creek all of his life.  Acles was born 20 Dec 1798 in Lee County, VA, the son of Elkanah and Mary Muncy Wynn.  He married in 1819 to Lucy Turner, daughter of William and Susannah Bailey Turner, who was born 10 Dec 1801 in Knox County (now Harlan County) and died about 1861 in Harlan County.  Acles and Lucy had eight children: Wright, Sarah, William, Hughner, Josiah, Elizabeth, Susanah, and Elkanah.

*Ballenger Calloway (1866) 1, 18 

Ballenger was born 17 Aug 1837, the son of Colonel Charles J. Calloway and Elizabeth H. Greene.  Col. Calloway came to Kentucky from the Yadkin River area of N. Carolina.  Ballenger married Mary E. Ball, daughter of Spencer Ball and Ellen Crabtree, on 3 May 1859 at Mary's parents home in Knox Co., KY.  Ballenger died 29 Dec 1914 at age 77.  Mary died 3 Mar 1916 in Bell Co., KY at age 73.

*William (Billie) Coldiron (period unknown) 21, 22

William was born ca. 1802 in Ashe Co., N. Carolina, son of Conrad Coldiron and Rachel Hendricks.  Conrad and Rachel moved their family to Knox Co., KY (now Harlan Co. area) in ca. 1808.  William married Leah Lewis in 1830 in Harlan Co.  We have found no official record of him being Sheriff, other than family legends and stories.  Oliver G. Coldiron, great-grandson of William, wrote a letter to his brother Dr. Daniel F. Coldiron dated 28 Mar 1917 wherein he stated:  ".... Billy Coldiron married a Lewis and lived down on Cumberland River.  He was above the average of his time and community.  He was Sheriff of his county at one time."  William died 1877 in Louisville, KY (although this location is questioned).  It is not known where he is buried.  There are 3,807 descendants of William and Leah documented.

William's position on this list is a guess; he could have been Sheriff anytime from the early 1860's to about 1880.  Much less is known about the officers in Harlan County during the 1860 ­ 1880 period which makes his exact placement uncertain.  Court sessions were rarely held during the Civil War, limiting court records during this period.

*Abner Lewis Coldiron (1882) 1, 22 

Abner was my great-grandfather.  He was born 2 Mar 1830, Harlan Co., KY, son of William (Billie) Coldiron (listed above) and Leah Lewis.  He married first to Lucy Ann Ball in about 1850, Harlan Co., KY, and they raised 11 children in Harlan Co.  Lucy Ann died in 1890 and Abner married second to Mary Farley on 3 Sep 1896 in Harlan Co.  This marriage ended in divorce.  Abner died 1 Jul 1911 in Baxter, Harlan Co., KY, living his entire 81 year lifetime in Harlan Co.  He is believed to be buried in the Old Coldiron Cemetery back of the Harlan Municipal Water Works in Coldiron Heights.  We have documented 1,009 direct descendants of Abner Lewis Coldiron and Lucy Ann Ball located across the United States.

*W. S. Hensley (1883 ­ 1884) 1 
This is probably the same Wilson Sergent Hensley listed for 1898.

*Ewell Van King (Jan 1885 ­ 1889) 1, 9 

He was born 20 Nov 1858, Harlan Co., KY, son of Alva Bird King and Rhoda Hensley.  In 1884 he married Mary (Polly) Skidmore.  Their first child was Addie King, who married Curtis Burnham Ledford.  Addie and Curtis are the subjects of the book Generations, by John Egerton.  Addie says her father was Sheriff of Harlan Co. for two terms, and then President Benjamin Harrison made him a U. S. Marshall.  Addie said her father died when she was about age 10 (ca. 1895).

*James L. Howard (1889 ­ 1890) 1 

*Abner Lewis Coldiron (1 Jan 1891 ­ 26 Jan 1893) 1, 22 

(See listing for 1882 for his first term as Sheriff.)  Abner served his second term as Sheriff from 1 Jan 1891 to Dec 1892.  He was elected to a third term in the fall election 1892 to be served in 1893 ­ 1894.  Shortly after beginning this third term in Jan 1893, he resigned from office, with his letter of resignation dated 21 Jan 1893 and his resignation accepted in Court session on 26 Jan 1893.  His letter of resignation written to W. C. H. Huff, Judge of the Harlan County Court, states in part:  "As there seems to be some trouble or delay concerning the bonds executed by me in your office and the condition of my family such that I hereby tender you my resignation as Sheriff elect for the year 1893 & 1894 asking your honor to make an order setting aside these bonds and appointing a Sheriff for the County...." 

* John C. Coldiron (26 Jan 1893 ­ 31 Dec 1893) 1, 10, 22 

John was my grandfather.  He was appointed Sheriff of Harlan Co. in a special January term of the Court on 26 Jan 1893 after the resignation of his father, Abner Lewis Coldiron (see above).  He was born in 1866, Harlan Co., KY, son of Abner Lewis Coldiron and Lucy Ann Ball.  He married Dora Skidmore 1 Nov 1888 in Harlan Co., KY.  We have documented 104 descendants of John and Dora.  John died 18 Sep 1897 in Harlan Co., KY at age 31 ­ cause of death is unknown.  The only record of his death is in Harlan County Court Orders, appointing a new guardian for one of John's wards. 10   John and Dora had three children, Harvey, Otto (my father), and Mary Ethel (who died at age 8).  Dora was the daughter of Abraham Skidmore and Margaret Farmer.  After John died, she remarried to Loyd Nolan on 22 Dec 1898 in Harlan Co. and they moved to Rose Hill, VA in 1917.

*Andrew H. Howard (1 Jan 1894 ­    ) 1 

*Grant Smith (1895) 1 , 26

Mabel Green Condon reports in her book on page 193: "In 1896 a man named Overton was hanged here because he was implicated in the murder of an old couple who peddled through the mountains.  It was the stern duty of Sheriff Grant Smith to cut the rope that sprung the trap, October 15, 1896, the day this boy was hanged."  Ms. Condon continues on page 194: "Grant Smith was the son of Jonathan P. Smith and Flora Ann Metcalf Smith who married June 15, 1848."

*Wilson Sergent Hensley (1898) 1, 20 

He was born 18 Mar 1858, Harlan Co., KY, the son of John H. Hensley and Elizabeth Sergent.  On 19 Dec 1883 he married Rachel Cawood in Harlan Co.  He died 25 Dec 1945 in Dayhoit, Harlan Co., KY and is buried in the Sergent/Hensley Cemetery in Rosspoint, Harlan Co., KY.

*John A. Ward (Jan 1902) 1 

*J. S. Kelly (Jan 1911 ­ Dec 1913) 1 

*Steve (Stephen) M. Cawood (1914 ­ 1917) 1, 19 

He was born in Cawood, Harlan Co., KY in Apr 1874, the son of Stephen and Virginia Cawood.  He married Laura Smith.  They had five daughters and three sons.  The family moved to Asheville, NC because of Steve's asthma problems.  He died 30 Jan 1924 in Asheville from asthma and is buried in the family cemetery in Cawood.  The article in The Harlan Enterprise stated that "He has always been remembered as one of the best sheriffs Harlan County has ever had."

*Hamp H. Howard (1918 ­ 1921) 1, 11 , 26

In addition to serving as Sheriff, he was once County Court Clerk and was also elected County Judge in 1929.  Author William D. Forester described him as ".... a friendly, intelligent man with a wonderful personality.  He had a knack for making friends and never saw a stranger.  His ability as a story teller was unsurpassed, and people delighted in hearing anecdotes he remembered about their ancestors, even as far back as great-grandfathers.  He was a natural-born politician."  In Mabel Green Condon's book, where she is discussing where people lived in Harlan, she says on page 25: "Sheriff Hamp H. Howard married Milly Carter and lived near the old Baptist Church on Third Street.  She was the sister of John Bradley Carter and Molly Carter Nolan.

*John Henry Blair (Jan 1922 ­ Dec 1925) 1, 12, 15   (Also see entry for 1930 to 1933.)

*James S. Green (1 Jan 1926 ­ 21 Dec 1926) 1, 15 

James defeated W. Floyd Ball in the Fall 1925 election.  Ball contested the results of the election, saying he had been counted out of the election by questionable vote counting at Lynch.  It took the remainder of the year to settle this in the courts, but in late December the court of Appeals affirmed that there was no legal Sheriff.  James resigned the office of Sheriff on 21 Dec 1926, and Judge W. J. R. (Willie Bob) Howard appointed his brother-in-law, George S. Ward, as Sheriff ­ to be Sheriff until the 1927 election.

*George S. Ward (21 Dec 1926 ­ 12 Nov 1927)  1, 13, 14, 15 

He was Secretary of the Harlan Co. Coal Miners Association while he served this term as Sheriff.  George also served as chairman of the Republican Committee in Harlan Co. in 1937.

*W. Floyd Ball (12 Nov 1927 ­ 6 Jul 1928) 1, 16, 28

He was son of Moses Ball and Sally Bailey.  Sheriff Ball and Dep. Sheriff John J. Hensley, nephew of former Sheriff Wilson Sergent Hensley, were murdered on the night of 6 Jul 1928.  Ball had received a call about 11:00 p.m. from the construction company building the road from Pineville to Harlan (Rt. 119 today).  They reported to Ball that some drunken men were running their cars over the newly laid concrete road and asked the Sheriff to come and arrest them.  Ball and Hensley hurried to the scene near the little village of Molus where they were shot.  Ball had spent his entire life in Harlan.  He had been a successful merchant in Harlan, Wilhoit, and Baxter, prior to entering the race for Sheriff.  He had been a member of the Harlan City Council and had been an active member of the Harlan Christian Church for 25 years.  He was married to Mary Morris.

*Leslie Fish Ball (7 Jul 1928 ­ 31 Dec 1929) 1

He was a brother to W. Floyd Ball above.  He was appointed to succeed Floyd by Judge W. J. R. (Willie Bob) Howard.  Leslie thus became the fourth man to serve as Sheriff during the four-year term 1926-1929.  Leslie was also Jailer of Harlan Co. (1930­1933) and also ran a men's clothing store.  He was born 8 Aug 1888 in Baxter, Harlan Co., KY, son of Moses Ball and Sally Bailey.  He married Mary Coldiron, daughter of Calvin Coldiron and Lucy Ann Newman and grand-daughter of Abner Lewis Coldiron, former Sheriff, on 22 Aug 1907 at Keith, Harlan Co., KY.  They had six children: Mildred, Gladys, Mable, Lucy, Leslie Jr., and Dorothy.

John Henry Blair (4 Jan 1930 ­ 30 Dec 1933) 1, 12, 13, 14, 15

Blair won the election in Nov 1929 by a slim 151 votes, and then served the first four years of the Turbulent Thirties.  His activities are well documented in the references.  He died 11 May 1934 after a three day bout against the poison of a ruptured appendix.

*Theodore R. Middleton (1 Jan 1934 ­ 31 Dec 1937) 1, 12, 13, 14, 17

Theodore was born Feb 1898, KY, the son of James H. Middleton and Josephine Lewis.  He was Chief of Police of Harlan prior to his election as Sheriff.  His tenure as Sheriff, during one of the most violent periods in Harlan Co. history, is well documented in the references.  Authors Titler 13 and Taylor14  both say he died in 1942 of a heart attack, but his tombstone in Resthaven Cemetery, Keith, Harlan Co., KY says 1897 ­ 1949.  William D. Forester of Harlan confirmed that he died in 1949.

*Herbert C. Cawood (Jan 1938 ­ 24 Jun 1938) 1, 12, 13

 Apparently, his election was contested (see entry below).

*Clinton C. Ball (25 Jun 1938 ­ 7 Nov 1938) 1, 12, 14

He was appointed Sheriff by Judge Cam E. Ball, Harlan Co. Court, the vacancy having been brought about by reason of a judgment in the Harlan Circuit Court declaring that there was no legal election held on 2 Nov 1937, for said office, and said judgment having been affirmed by the Court of Appeals of Kentucky and the mandate of said Court of Appeals having issued and been filed in the office of the clerk of the Harlan Circuit Court.

*Herbert C. Cawood (10 Nov 1938 ­ Dec 1941) 1, 12, 17

After having his previous election overturned by the courts, Herbert was elected once again in Nov 1938 to serve the remaining three years of the four year term.

*C. C. Ball (Jan 1942 ­ Dec 1945) 7

It is assumed this is the Clinton C. Ball who served the terms in 1938 and 1950.  The Harlan Co. Court Orders never mentions his first name during the four years of this term.

*James S. Cawood (Jan 1946 ­ Dec 1949) 7

*Clinton C. Ball (Jan 1950 ­ Dec 1953) 7

*William S. (Bill) Hensley (Jan 1954 ­ Dec 1957) 7

*William S. (Bill) Hensley was b. 24 Jan 1916 and d. 15 Jul 1969. 
He is buried in Resthaven Cemetery.

*Jay Barlow (Jan 1958 ­ Dec 1961) 7

*Robert M. (Bob) Hall (Jan 1962 ­ Dec 1965) 7, 25

 For details on Robert M. Hall, see Harlan Heritage XIII, March 1998, page 2B.

*Jason F. Howard (Jan 1966 ­ Dec 1969) 7

Walden Holbrook (Jan 1970 ­ Dec 1973) 7

*Billy G. Williams (Jan 1974 ­ Dec 1977) 7

*Harold Edward Howard (Jan 1978 ­ Dec 1981) 7, 22

Harold is the son of Jonathan Daunt Howard and Una Cleo Coldiron, and the great-grandson of Abner Lewis Coldiron, former Sheriff.  Harold was born on 25 Jan 1923 in Baxter, Harlan Co., KY.  He married Elizabeth Duncan on 28 Sep 1943 in Baxter.  For several years he operated the Mayo Trail service station in Baxter previously operated by his father.  At one time he was the Magistrate for Harlan.  Harold's and Elizabeth's son Daniel was mayor of Harlan in 1995 and their daughter Frieda is a school teacher in Barbourville, KY.  In 2002, Harold is living in the Coldiron Heights area of Baxter.

Paul Louis Browning  Jr. (Jan 1982 ­ 1982) 7, 27

Paul Browning was born in Verda, Harlan Co., KY on 20 Feb 1945.  He was elected Sheriff in 1981 on a campaign of routing out corruption and bootlegging.  He was arrested the next year amid accusations that he conspired to kill a local magistrate and the county school board chairman.  He was sentenced to 10 years in prison in 1982 after being convicted of two counts of conspiracy to commit murder.  He was paroled after about three years in prison.  After his release, the conviction was overturned in 1986.  He was convicted again in a 1987 retrial, but did not serve  additional prison time.  He left for Ohio in 1988, vowing to return to Harlan County someday and run for sheriff.

He was running for re-election to Sheriff in 2002, and on Friday, 22 March 2002, told family members he was headed toward the Pathfork section of Harlan County to campaign.  On Saturday, 23 March, his charred body was discovered in his burned pickup truck on Tanyard Hill in Bell County, KY, about five miles from the Harlan County line on KY 2012 off US 119.  The incident is being investigated as a murder.  Paul was a Vietnam War veteran and was married to Jayne Hall.

*W. B. Redwine (Jan 1986 ­ Dec 1993) 7

*Steve Duff (Jan 1994 ­ present) 7

1 Harlan County Court Orders and Records (1829 ­ 1950)
2 Harlan Footprints, Vol 1, No. 1, pg. 11
3 Harlan Footprints, Vol 1, No. 1, pg. 10
4 Harlan Footprints, Vol 2, No. 1, pg. 25
5 Harlan Mountain Roots, Vol 7, No. 1, pg. 9
6 Harlan Mountain Roots, Vol 7, No. 1, pgs. 15 & 26
7 Harlan County Election Results (1950 ­ present)
8 Harlan Footprints, Vol 1, No. 2, pg. 26
9 Generations, by John Egerton, pg. 33
10 Harlan County Court Records, 4 Oct 1897, pg. 599
11 Heritage III, pg. 26 (published 28 Feb 1986 by Harlan Daily Enterprise)
12  Harlan County ­ The Turbulent Thirties, by William D. Forester
13 Hell In Harlan, by George J. Titler
14 Bloody Harlan, The UMW of America in Harlan Co., KY ­ by Paul F. Taylor
15 Before We Forget ­ by William D. Forester
16 The Harlan Daily Enterprise ­ 7 Jul 1928
17 Harlan Goes To War ­ by William D. Forester
18 Harlan Mountain Roots, Vol 1, No. 1, Fall 1986, pg. 33
19 The Harlan Daily Enterprise ­ 1 Feb 1924
20 1900 Census
21 Letter, Oliver G. Coldiron to Dr. Daniel F. Coldiron, 28 Mar 1917 plus family stories.
22 A Genealogy of the Coldiron Family, compiled by Otto G. Coldiron, 1997
23 Harlan Mountain Roots, Vol 1, No. 3, Spring 1987, pages 112-114.
24 E-mail from Mary J. Harris, 17 July 2000
25 Harlan County Heritage XIII, 1998, page 13B
26 A History of Harlan County, by Mabel Green Condon
27 The Harlan Daily Enterprise ­ 28 March 2002
28 The Harlan Daily Enterprise ­ 13 July 1928

Readers are once again cautioned that the information presented above is from a variety of sources, and some is not verified against original sources.  The information is from notes gathered over many years of research, and accuracy is therefore not guaranteed.  I welcome any inquiries or comments from readers on this list and the information it contains.  I would like to correct any errors the list contains.  Please send any new information or corrections to the address at the beginning of the article, or call me at (352) 754-5075, or e-mail at:  <>. 

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