Jim Boy, or High Head Jim, (1851) also called Tustennuggee Emathla and Kasita Hadjo, was a 19th-century Native American leader of the Creek Confederacy (Muscogee, ) in southeastern North America. He was associated with the Red Sticks political party within the tribe, and has been classed as one of the "prophets" of that era. He was "almost certainly" of mixed Creek–Black ancestry. He fought semi-organized American militia during the First Creek War, mostly notably at the Battle of Burnt Corn in 1813, and saved the lives of his adoptive mother and sisters at Fort Mims. Some 20 years later, during the Andrew Jackson administration, he was recruited by the United States Army to fight the Seminoles in Florida during the Second Seminole War, in exchange for promised money, debt forgiveness, and protection for his family back in Alabama. His wife, children, and slaves were deported while he was still in service; four of his children and three of his slaves were among the estimated 250–325 people killed in the steamboat Monmouth disaster on the Mississippi River in 1837. Following the expulsion and deportation of the Five Civilized Tribes from their ancestral lands east of the Mississippi, Jim Boy and his family settled on the Creek Nation land in what is now eastern Oklahoma. Tustennuggee Emathla, or , is not exactly a name, but a title; it translates very roughly to warrior of experience and rank. His portrait is plate 6 in volume 11 (P27759) of McKenney and Hall's History of the Indian Tribes of North America. His many names have complicated his biography; most sources assert that that Jim Boy and High-Head Jim are the same historical character, but in 2006 archaeologist Christopher Waselov wrote, "The Creek who rescued McGirth was Jim Boy, possibly the same man known as High-Head Jim, though probably not."

Early life and Fort Mims Jim Boy's birthplace and the identities of his biological parents are not reported in extant histories of the Muscogee. There are semi-reliable statements of his age that place his birth year in either 1791 or 1793. According to a 1939 account by Alabama state archivist Peter A. Brannon, Jim Boy was "an orphan entitled to the chieftancy of the Atassees...reared in the family of Mrs. Zack McGirth, widow of Gen. Alexander McGillivray, [he] grew up with her daughters. He saved the life of Mrs. McGirth and her girls and protected them from harm at the Fort Mims massacre." The Fort Mims Restoration Association website retells this story from McGirth's point of view and calls Jim Boy Sanota. Zack McGirth ran a whiskey still on Persimmon Creek (GNIS 152875), "near a lettered beech tree on the Federal Road," possibly slightly to the east of Fort Hull. McGirth was married to Vicey Cornells, said to be "the second daughter of Joe Cornells."

A man who investigated the execution of William McIntosh noted in his journal that Jim Boy "had negro blood." Ethan Allen Hitchcock described Jim Boy in his war journals as "a colored mixed." Thomas L. McKenney asserted that Jim Boy was "a full-blooded Creek." He is named as Jim Boy in some accounts and High Head Jim or High-Headed Jim in others. The name by which he is identified in the primary portrait of him is a title held by Muscogee and Seminole leaders, but researchers disagree as to how many ranks actually existed and the correct terminology for the different ranks. Most of the literature points to four ranks of warriors: unranked warriors (little emarthla or tasikyalgi), warriors (big emarthla or tastanagi), war chiefs (tustennuggee or tastanagi tako), and the Great Warrior (tustennuggee thlocco or isti puccanchau thlucco). Warriors of higher ranking were provided seating at council meetings around the squareground, the center of Creek life and their talwa settlements."

First Creek War and interwar period During the Creek War of 1813–1814 he was "Chief of the Autosees". According to an affidavit by bilingual Muscogee-native planter and interpreter named Sam Moniac (also called Sam Manac or Totkes Hajou), he encountered High Head Jim during the second week of July 1813, who apprised of the optimistic Indigenous war plan to arm the tribes with British weapons and ammunition and unite against the American settlers who encircled them:

In the telling of American general and Muscogee chronicler Thomas Simpson Woodward, the Battle of Burnt Corn was an unplanned skirmish fought when Jim Boy and Peter McQueen were returning from a mission to Pensacola to buy ammunition for the obviously forthcoming war; "I have heard Jim tell it often, that if the whites had not stopped to gather up pack horses and plunder their camp, and had pursued the Indians a little further, they [the Indians] would have quit and gone off. But the Indians discovered the very great disorder the whites were in, searching for plunder, and they fired a few guns from the creek swamp and a general stampede was the result. McGirth always corroborated Jim Boy's statement as to the number of Indians in the Burnt Corn fight. I have seen many of those that were in the fight, and they were like the militia that were at Bladensburg—they died off soon; you never could hear much talk about the battle, unless you met with such a man as Judge Lipscomb, who used to make a laughing matter of it." Jim was at the Fort Mims massacre on August 30, 1813, "Jim Boy succeeded in saving Mrs. McGirth and her daughter, but her only son, James, was killed...After the Fort fell, and Jim Boy saved Mrs. McGirth and tried to save others, the Indians ran him off, and it was some time before they would be reconciled to him."

The settlement of Atasi was destroyed by the Georgia militia at the Battle of Autossee of November 29, 1813. According to the account of George Stiggins, "In said Autussee battle the hostiles supposed that they lost in killed Eighty men and upwards of a hundred wounded their complete defeat with the burning of their town broke up the hostile settlement in the Autussees[.] it gave them a complete scare and set them to rambling[.] many of them took up their quarters in the Othlewalle camps[.] some made their way with their families to inaccessible places in the swamps of the forest and others went for Pensacola for safety among the Spaniards, the hostile camps by this time began to feel the want of ammunition there being a general scarcity of that article among them, so there was a general meeting called by the hostile chiefs and prophets, to take into view their situation and state of affairs..." The account of the mixed-race Indian trader and Indian agent Stiggins, written in the 1830s, also states that Jim was called Cussetaw Haujo and asserts (inaccurately, it seems) that he was killed at the Battle of Calebee Creek.

After the war Jim Boy lived at Thlopthlocco near Polecat Spring and Cubahatchee Creek (GNIS 151750), a left-hand tributary of the Tallapoosa River. Thlopthlocco means "big cane" or "tall reed" (perhaps originally referring to nearby canebrakes), and is pronounced "thlop-thloc'-oh." Polecat Spring was on the main road from Chattahoochee and was the site of an Indian subagency. It was located in what is now Macon County, Alabama, near Shorter.

In 1818, during the First Seminole War, Jim Boy reportedly fought with William McIntosh "against the Seminoles". Another account names him as Gun Boy and reports that he was taken prisoner by the Americans "before Fort Gaines." Thus, writes historian Kathryn Braund, there is no agreement on Jim Boy's involvement in the first Seminole War.

Treaties, pre-expulsion era Following the Treaty of Indian Springs in 1825, as Creek headmen were trying to discourage voluntary immigration to the west, "Tuskeneah...along with the former Red Stick prophet Jim Boy, drew a sword and threatened to kill John Reed of Thlewallee and William J. Wills of Thlakatchka while at Reed's mother's house near Line Creek." In 1832, Jim Boy was listed on the "Parsons and Abbot Census as the headman of Cle walla Town (Hoithlewaule). That town was a Red Stick town during the Creek War."

Jim Boy lived about west of Montgomery, on the way to Auburn, and a little southwest of Tuskegee. This land was ceded to the U.S. government in 1832 at the Treaty of Cusseta. He was "one of the 90 'mile chiefs' selected by the Creeks in Council to receive a full section of land under the 1832 Treaty of Washington."

Western land reserves that were to distributed to the Creeks in exchange for the eastern lands were handed out in a disorderly manner. In addition to poor recordkeeping and mismatches of who was supposed to be entitled to get what, Seminoles Coathlocco, Talladig Harjo, Cochus Harjo, and Charley Emathla of Davy's (or Cockrane's) town "were persuaded by the Creek Indian Jim Boy to emigrate from Florida to Alabama and acquire land under the 1832 treaty".

Second Creek War During the Second Creek War in 1836, "he attached himself to the friendly party." He led a troop of counterinsurgents "who aided the United States during the war" who "happened upon Neah Micco's camp in June 1836 and found captured slaves, as well as expensive furniture, writing paper, china, and cut glass. They also found provisions such as 'purloined beef, bacon, and pork in large quantities, both cooked and uncooked.'" Jim Boy led the detachment that captured Neah Emathla.

Second Seminole War Solicited by Thomas Jesup of the United States Army, he and Paddy Carr led 767 Creeks against Seminoles in the Second Seminole War. According to historian Christopher Haveman, U.S. Army officers "enticed the Creeks to volunteer with various promises. For instance, the Creek headmen who served in Florida received $10,000―to be disposed of as they may see fit, if the Creeks under their command performed in good faith. The government also promised to use their 1837 annuity to pay off accumulated debts and to get clear of the ruinous suits against them. An agent was also appointed to settle their land claims. The Creeks who served were organized into companies and paid for their services as soldiers. Those with horses were paid as mounted volunteers. In addition to the government's offerings, the Creeks made demands of their own. The first was that their family members be allowed to remain in Alabama under the protection of the federal government until their tour-of-duty was completed. The government subsequently placed the Creek family members in three large encampments at Polecat Springs, Echo Harjo's home thirty miles east of Polecat Springs, and at Fort Mitchell. Here the relatives of the warriors were issued provisions and protected from local white settlers."

These Creeks were organized into a regiment and put under command of Major David Moniac. Jim Boy fought with this regiment in the Battle of Wahoo Swamp in November 1836 and the Battle of Lake Monroe in February 1837. In fall 1837 over 2,000 Creeks "still remained at Mobile Point waiting for their warriors to be discharged from service in Florida. While the delay in the return of the Creek warriors from Florida had allowed the Creek family members in Alabama to be victimized by white settlers, the delay also allowed the Creeks now at Mobile Point to be exposed to sickness," and people began dying from "diarrhea, dysentery, and intermittent fever." After being relocated for a time to the more healthful Pass Christian, on October 16, 1837, headman Jim Boy and approximately 200–300 other Muscogee boarded the steamboat Mazeppa for New Orleans where they transferred to the steamboat Cavalier to travel up the Mississippi River and thence to the Arkansas River en route to Fort Gibson, in what is now Muskogee County, Oklahoma.

Removal, disaster, and Indian territory