[6] The town gets its name from James Jackson McAlester, an early settler and businessman who later became lieutenant governor of Oklahoma.

[6] McAlester is the home of the Oklahoma State Penitentiary, the former site of an "inside the walls" prison rodeo that ESPN's SportsCenter once broadcast.

At the time of its founding, the site was located in Tobucksy County, a part of the Moshulatubbee District of the Choctaw Nation.

[8] Alyssia Young, who emigrated from Mississippi to the Indian Territory, first established a settlement at the intersection of the two roads in 1838.

The town was named Perryville after James Perry, member of a Choctaw family, who established a trading post.

On August 26, 1863, a force of 4,500 Union soldiers crossed the Canadian River and destroyed the Confederate munitions depot at Perryville.

After the end of the Civil War in 1865, Captain J. J. McAlester obtained a job with the trading company of Reynolds and Hannaford.

He had learned of coal deposits in Indian Territory during the war while serving as a captain with the 22nd Arkansas Infantry Regiment (Confederate).

Hearing of the railroad plans to extend through Indian Territory and knowing that rich deposits of coal were in an area north of the town of Perryville, McAlester convinced Reynolds and Hannaford that Bucklucksy would be a more suitable and profitable site for the trading post.

Several New York businessmen, including Levi P. Morton, Levi Parsons, August Belmont, J. Pierpont Morgan, George Denison and John D. Rockefeller, were interested in extending rail through Indian Territory, and the Missouri-Kansas-Texas Railroad, familiarly called the Katy Railroad, began its corporate existence in 1865 toward that end.

[11] That same year, J. J. McAlester, after buying out Reynolds's share of the trading post, journeyed with a sample of coal to the railroad town in hopes of persuading officials to locate the line near his store at Bucklucksy.

The line reached Bucklucksy in 1872, and Katy Railroad officials named the railway stop McAlester (Nesbitt 1933, pp. 760–61).

McAlester quickly obtained land near the intersection of the north–south and east–west rail lines, where he opened a second general store and continued selling coal to the railroads.

[6] In 1885, Fritz Sittle (Sittel), a Choctaw citizen by marriage and one of the first settlers in the area, urged visiting newspaperman Edwin D. Chadick to pursue the possibility of an east–west rail line to run through the coal mining district at Krebs that would connect with the north–south line at McAlester.

Chadick eventually found financing and established the Choctaw Coal and Railway in 1888, but was unable to come to terms with J. J. McAlester over the issue of right of way.

[12] McAlester was on the route of the Jefferson Highway established in 1915, with that road running more than 2,300 miles from Winnipeg, Manitoba to New Orleans, Louisiana.

It has a humid subtropical climate (Cfa) and average monthly temperatures range from 40.0 °F (4.4 °C) in January to 81.7 °F (27.6 °C) in July.

[21][22] During World War II, the U.S. Government built the Naval Ammunition Plant a few miles south of McAlester.

The Wanda Bass Higher Education Center, a branch of Eastern Oklahoma State College, is also in McAlester.