|Appearances:||Sharpe's Company, Sharpe's Enemy|
When Hakeswill was 11, his mother, Biddy, died, and at the age of 12, he attempted to rape a young girl in his home village, threatening her with a snake. To protect the girl's reputation, however, Hakeswill was convicted of another crime: stealing a sheep; and he was sentenced to death by hanging. The hanging failed to kill him, however, and his uncle cut him down. He escaped and fled to enlist as a drummer boy in the 33rd Regiment of Foot.
The hanging left him with an obvious scar on his neck, and an uncontrollable facial tic. Hakeswill rose to the rank of sergeant, due to his punctilious observation of military protocol in front of officers. Out of their sight, however, he terrorized his men who both hated and feared him. Hakeswill treated the men beneath him viciously, using intimidation and strong-arm tactics, as well as nitpicky charges against lost and stolen equipment to make the troops fear him and to enrich himself through extortion. About 1793, he recruited then 16-year-old Richard Sharpe to the 33rd.
In India, with the collusion of his commanding officer, Captain Morris, he succeeded in having Sharpe sentenced to 2,000 lashes (essentially a death sentence). Sharpe got away with only 202 of the sentence after intervention from Sir Arthur Wellesley.
Sharpe tried to kill Hakeswill in Sharpe's Tiger, by locking him in a compound with six tigers belonging to the Mysore Tippoo, as revenge for his actions against him; however, as the tigers had already eaten, Hakeswill survived.
After Sharpe was promoted to Sergeant, Hakeswill again tried to destroy the younger man, and manufactured an assault which led to an arrest warrant for Sharpe. He was again thwarted when Sharpe's patron, Colonel Hector McCandless, said the warrant was no good as Sharpe's name was spelled incorrectly on it. Furious at being thwarted, Hakeswell later murdered McCandless in the confusion of battle - something he had done before to officers he did not like, and would try again.
He reappeared in Sharpe's life in Sharpe's Company, still a sergeant but attached to the replacement troops sent to the South Essex. He attempted to rape Teresa, who intrigued him when she showed no fear. She escaped his hold, and cut him. Sharpe and Harper arrived in time to offer a few blows of their own. He conspired to remove Harper, a fellow sergeant and a threat, so planted stolen items in his pack. Harper was demoted and flogged, earning Hakeswill Harper's hatred along with Sharpe's.
He then convinced his untried Captain, Rymer to take away the green jackets and rifles of Sharpe's men, and turn them in to musket-carrying redcoats, confiscating Harper's volley gun for himself. He attempted to murder Sharpe during a night action, but succeeded in killing a teenage ensign and only wounding Sharpe.
Hakeswill overhead the location of his Sharpe's family inside Badejoz, and was obsessed with Teresa. He arrived at the Moreno house at the same time as Robert Knowles who was determined to protect Sharpe's family. He murdered Knowles and threatened Sharpe's daughter, Antonia, with a sharpened bayonet. Harper, Sharpe, and Teresa all tried to kill him, but he escaped, leaving Antonia with a single scratch at her throat. He then deserted, knowing he, at last, left too many crimes to cover.
He reappeared in Sharpe's Enemy as a self-styled colonel in the deserter army under Pot-au-Feu. They captured several women whom they held hostage, Sharpe was one of those who arrived with ransom money. The money and the women were kept, however, and Sharpe led a rescue, routing the deserters.
Captured, Hakeswill was stripped naked and left in the dungeon with the other prisoners. He cursed Sharpe, and then stole a great coat so as to escape in the confusion of the last minutes of the battle between the French and British in the pass outside. Teresa arrived with Nairn and the British reinforcements at the same time, and spotted Hakeswill fleeing across the snow. She rode after him, hating him as much as her husband had for his previous threat to her daughter. She lifted her blade to kill him, when he spun, firing his musket blindly, the bullet caught her in the throat, killing her instantly.
He fled to French lines, but Colonel Dubreton returned the deserter to a devastated Sharpe. The prisoner was taken to Frenada and condemned as a murderer and deserter. The South Essex provided a firing squad of fourteen men. Hakeswill fought the ropes that held him, Sharpe didn't bother to watch as they fired, it no longer meant anything. Still alive after the volley, Sharpe approached him with his rifle for the coup de grace. Hakeswill cried out several times, "You can't kill me," when Sharpe proved him wrong, even as he fulfilled his vow to see Hakeswill killed in front of his victims, rather than secretly murdered.
He was buried in an unmarked grave, marched over by his regiment to eradicate any sign of the site.
In Sharpe's Company, Hakeswill attempted to rape Sharpe's wife, Teresa Moreno, but was caught by Patrick Harper and beaten. He then pursued Sally Clayton, the wife of a fellow soldier. Harper threatened Hakeswill upon being told of Hakeswill's acts, so Hakeswill framed Harper for theft. Harper received 100 lashes and a demotion leaving Hakeswill ranking sergeant. He then confiscated Harper's Volley Gun, and used it himself in an attempt to kill Sharpe during a battle. He missed and killed a young ensign instead.
During an assault on a French-occupied town, Hakeswill avoided combat by hiding under the corpse of a British officer. After the French were defeated, Hakeswill proceeded with many of the other soldiers over the wall of the town. He followed Harry Price to the Teresa's house. He shot Harry and threatened Antonia, but Sharpe and Harper arrived in time to rescue them, using the portrait inside Hakeswill's shako. He had recently begun talking to the portrait calling it Mother, Sharpe spat on it and Hakeswill went mad abandoning Antonia. Hakeswill once again cheated death and survived, though wounded by Harper. He then fled and deserted the army.In Sharpe's Enemy, Hakeswill joins a large group of British, French and Portuguese deserters, who captured Sarah Dubreton the English wife of a French colonel, Michel Dubreton, and Lady Farthingdale, the wife of a British colonel, Sir Augustus Farthingdale.
Hakeswill demanded, from both the British and the French, ransom in gold in exchange for the release of the two women. Sir Arthur Wellesley sent Sharpe and Harper to give the deserters the ransom provided by Farthingdale. Sharpe arrived at the deserter's fortification with the gold, but Hakeswill doubled the ransom, saying they had simply purchased their virtue, not their freedom. Mistrusting Hakeswill, Sharpe and the Rifles launched an assault, freeing the women and defeating the deserters.
Hakeswill, however, escaped and kidnapped Lady Farthingdale after her release, but Teresa pursued and confronted him, and he shot her dead.
Handed over to the British, Hakeswill faced execution by firing squad, which failed to kill him, so the officer in charge of the firing squad proceeded to shoot him in the heart at point-blank range, finally killing him.
Hakeswill was a deeply sadistic man with no objections to abusing, manipulating and murdering people. He was also likely insane. One of his delusions was that he believed he couldn't be killed. Hakeswill would also often talk aloud to his mother and at one point kept a portrait Col Windham's wife in his hat, which he also talked to, calling it mother.
- Cornwell regretted killing off Hakeswill, saying that good bad guys were hard to find.