Some people are under the impression that bureaucratic red tape, particularly in the form of the Internal Revenue Service, is a 20th century invention. Although it is true that nowadays we have to cope with tax forms ourselves, complicated taxes have been around quite a while. The surviving tax lists of the 19th century not only provide various details and information about the individuals listed, but they also show the slow but sure growth of the area early in the 19th century.

In 1819, when Harlan was formed, most white males over the age of 21 were taxed at a rate set by the county court. The few who were exempted from this tax, or tithe as it was called, were excused usually due to their age, apparently at about 65 years old.

In 1820, Berry Cawood, Henry Shackleford and Jonathan Kelly Sr., were all excused from paying the tithe for reasons unstated, but from other information regarding their ages, it is certain it was their advanced years that so excused them. That same year William Morgan was exempted "from paying county levy in future in consequence of inability."

Cawood, Shackleford and Kelly had all been named on the list provided by Knox County in 1819 detailing the 243 white males over the age of 21 who were residents of the section of Knox County that became the newly created Harlan County. As it took a while for Harlan County to get properly organized, the 1819 Harlan tax lists is in fact filed with the Knox County lists for that year.

For the first half of the 19th century, individuals were also taxed for the land they owned at varying rates; for their slaves on which they not only paid a value tax as on any property, but they also paid a head tax on each and every slave over the age of 16; for the value of their horses, mares and mules, with an additional tax for a stud horse; for retail or wholesale businesses and tavern licenses and for billiard tables and wheeled carriages.

With the organization of the county seat of Mount Pleasant, now the city of Harlan, a column was added to the tax lists in 1821 showing ownership of town lots. Only one or two taverns are listed in the early years as in 1838 when the totals for the lists give 448 voters, 598 children between the ages of 7 and 17 and one tavern.

From 1840 onwards, the tax lists expanded rapidly covering more and more types of property in more and more detail. By 1843, cattle, pianos, gold spectacles, gold watches and silver lever watches were listed. John McGeorge had a silver watch and the two stores listed for the county were Unthank & Ballenger and G.R. Jones & Company. In the 19 years since 1821, the number of white males over the age of 21, and thus voters, had increased to 540. There were 940 children between the ages of five and 16 and 77 slaves of all ages.

Two years later, in 1845, Unthank & Ballenger were still in business and Elijah Creech and Jonathan Kelly were each operating stores. In 1850, William Turner, Jr., owned two stores and a tavern license. Ewell V. Unthank is listed as sole owner of a store, and another store, probably up Poor Fork in the vicinity of present day Cumberland, was being operated by Creech and Richmond. Turner and Carlo B. Brittain had silver watches and the recently added columns to list individuals who were blind, deaf or dumb shows a blind person in George Howard's household, probably the Ephraim Osborne who is listed in this household in the 1850 census as being 105 years old.

By 1852, Harlan had on its tax rolls 480,923 acres of land; 25 town lots; 119 slaves, 47 of whom were over the age of 16; 1,222 horses and mares; 30 mules, 2 jennies; 6,518 head of cattle over the $50 value exemption; 4 stores; 3 taverns; 8,667 hogs over the age of six months; 728 males over the age of 21; 1,371 children between the ages of 5 and 16; and three silver watches.

By 1860, much more detailed information was being sought by the assessor's office. Gold and silver plate, clocks, pounds of tobacco or hay, bushels of corn, wheat or barley, tons of pig metal or bar iron and hogs over the age of six months were among the columns added to the inquiries and the carriage classification had been broken down into pleasure carriages, barouches, buggies, stage coaches, gigs, omnibuses and other vehicles for passengers.

In 1859 and 1860, several people were named in response to the column on blind deaf or dumb. These included James and Martha Osborne's daughter Catherine (blind); Rollin Eversole's son William (dumb); James Huff (blind) living with his grandson, Hiram Huff; and Jane Bailey (deaf & dumb), daughter of Jesse and Mary Parsons Bailey. A curious note about Jane Bailey was added to the 1852 tax list, "She is very sprightly for a person in her condition and if educated would be a satisfaction to herself and friends and a useful member of society."

Several changes in the lists occurred in the 1860's regarding the longstanding slave information columns. For many years these had read: number of slaves over age 16, total number of slaves and total value of slaves. In 1863, a column appeared for "Free Negroes" and, in 1866, with the end of the Civil War, the three older columns were scratched out and new headings written in by hand: number of dogs over 2, number of sheep killed by dogs, and value of sheep killed by dogs. In 1867, these columns appear as printed headings and a listing of non-residents and of Negroes appears at the end of the tax lists.

In the following years there are a number of minor changes and additions and then, in 1888, a large number of detailed columns were added, bringing the total number to 100 columns. These columns asked for detailed information on livestock including whether thoroughbred or common mixed breed; on personal possessions such as jewelry or diamonds, household furniture over $250, paintings other than family likenesses, professional libraries, safes, sewing and knitting machines; on business property such as wines, whiskies, steamboats, patent rights, steam engines, slaughtered animals; on financial matters such as credits or money at interest, money in possession, bonds, stocks, and judgements; additional agricultural information such as acres divided by meadow, woodland, corn and wheat. It was that year when coal was added to the minerals columns for the first time.