The first people to live in the area of Winkler County were the Anasazi Indians, who migrated there about 900 AD and left their discarded pottery as evidence of their presence.

The first military expeditions entered the area of present-day Winkler County in the last half of the 19th century.

Captain Randolph B. Marcy brought his soldiers into the area on September 25, 1849, as he searched for the best wagon route to California.

John Pope surveyed the 32nd parallel, which separates Winkler County from New Mexico, for possible railroad construction in 1854.

On June 29, 1875, Col. William R. Shafter, accompanied by 81 men and officers, tracked the Comanche Indians into county lands, when Col. Ranald S. Mackenzie conducted a campaign to drive them from the area.

By 1876, all threat of Comanche attack was eliminated and the area of Winkler County was opened for White settlement.

In 1881, the Texas and Pacific Railway was built across nearby Ward County, giving easy access to the area.

In the census of 1900, 12 ranches, totaling 67,537 acres (273.31 km2) and 11,982 cattle, were operated by four owners and eight nonowners, and the county population was 60.

Since one could purchase four sections of land on generous credit terms, Winkler and other West Texas counties experienced a school-land rush as new settlers arrived.

Lots in the townsite of Duval were widely promoted, and the town competed with Kermit for the county seat.

In the presidential election of 1908, Winkler County supported William Jennings Bryan, the Democratic candidate.

Although the number of farms had increased by 1910, only small hay and corn crops were harvested on 230 acres (0.93 km2) of farmland.

A drought swept across Winkler County in 1916, and many families who came during the school-land rush gave up their farms and moved.

[4][5] The boom established the town of Wink in the southwestern part of the county, 7 mi (11 km) southwest of Kermit.

The increased population caused a housing shortage and forced newcomers to live in tents and makeshift structures, mainly in Wink.

A post office opened at Tulsa in southern Winkler County on August 20, 1927, but it closed in 1929 when the town failed to boom as its namesake had.

By 1970, the oil industry had experienced a decline in West Texas, and the population in Winkler County dropped to 9,640.

By 1980, West Texas had experienced a dramatic oil boom with greatly increased drilling activity and an influx of new people in blue-collar jobs.

Roberts, armed with search warrants, set to work finding out who had contacted the medical board.

After obtaining confidential medical records based on protected private health-care information provided by Arafiles, Roberts brought the case to the prosecutor.

County attorney Scott Tidwell sought to prosecute the two nurses for misuse of official information, a felony that carries a possible $10,000 fine and a 10-year jail sentence.

The pair had been members of the administration responsible for credentialing physicians, quality assurance, and risk management.

Hospital administrator Stan Wiley was indicted on felony retaliation charges and accepted a plea deal in March 2011, where he pleaded guilty to a misdemeanor in exchange for cooperating with the state.

[11] Arafiles also cut a deal with prosecutors and pled guilty in exchange for 60 days in jail, the surrender of his medical license, a $5,000 fine, and 5 years probation.

[12] Mitchell and Galle sued Winkler Memorial Hospital, the county, the sheriff, Wiley, Arafiles, Tidwell, and District Attorney Michael Fostel in United States District Court on August 29, 2009, for deprivation of rights, vindictive prosecution, conspiracy to interfere with employment relationship, violation of the Texas Whistleblower Act, and assorted other claims.

[15] The climate is generally dry, and in spring and summer, it is hot; the hottest daily maximum temperatures in the continental US are often recorded in lower elevation areas near the Pecos River in the county, particularly during April, May, and June.