|Appearances:||Sharpe's Company, Sharpe's Enemy|
Sergeant Obidiah Hakeswill was a soldier in the British army. He was portrayed in the TV series by Pete Postlethwaite.
At the age of 11, Hakeswill's mother died and at the age of 12, he sexually assaulted a young girl in his hometown. However, to protect the girl's reputation, Hakeswill was convicted of another crime; stealing a sheep. He was sentenced to death by public hanging. However, the hanging failed to kill him, and he escaped his hometown and fled south, to enlist as a drummer boy in the 33rd Regiment of the British Army. The hanging left him with a large scar on his neck and an uncontrollable facial tic. Hakeswill rose to the rank of sergeant later in his military career and recruited Richard Sharpe in the 1790s, but in later campaigns in India and Flanders, Hakeswill treated Sharpe and the other soldiers extremely poorly, and eventually tried and succeeded to have Sharpe sentenced to 2000 lashes (essentially a death sentence). Sharpe got away with only 200 of the 2000 lashes after intervention from Sir Arthur Wellesley.
Obidiah had a penchant for stealing and laying the blame upon other soldiers. When Obidiah re-encountered Sharpe, he was a captain (and briefly demoted to lieutenant) and treated Hakeswill poorly, just as Hakeswill had done to him. Hakeswill attempted to rape Sharpe's wife, Teresa Moreno, but was caught by Patrick Harper and beaten up. He then pursued Sally Clayton, the wife of a fellow soldier. Harper threatened Hakeswill upon being told of Hakeswill's horrible acts, so Hakeswill framed Harper for theft. Harper received 100 lashes. He also confiscated Harper's Volley Gun, and used it himself in an attempt to kill Sharpe during a battle. He missed and killed a young officer instead. During an assault on a French-occupied town, Hakeswill avoided combat by hiding under the corpse of a British officer that he stabbed. After the French were defeated, Hakeswill proceeded with many of the other soldiers to begin pillaging the town. He followed Harry Price to the building in which Teresa was hiding. He shot Price and kidnapped Teresa, but Sharpe arrived in time to rescue her. Harper then shot Hakeswill with his Volley Gun, but Hakeswill once again cheated death and survived with only a slight wound. He then fled and deserted the army after raping and murdering Sally Clayton (Sally's husband had died in the assault).
Hakeswill then joined a large group of British, French and Portuguese deserters, who captured Sarah Dubreton (the English wife of a French colonel, Michel Dubreton) and Lady Isabella Farthingdale (the half-Portuguese wife of a British colonel, Sir Augustus Farthingdale). Hakeswill demanded, from both the British and the French armies, ransom gold in exchange for the release of the two women. Sir Arthur Wellesley sent Sharpe and Harper to give the deserters the ransom, a decision which Augustus Farthingdale disapproved of. Sharpe arrived at the deserter's town with the gold, but Hakeswill doubled the ransom. Mistrusting of Hakeswill, Sharpe and the 95th Rifles launched an assault on the town, freeing the two women and defeating the deserters. Hakeswill, however, escaped and kidnapped Isabella Farthingdale after her release, but Teresa pursued and confronted him. Hakeswill shot Teresa, wounding her mortally, but he was captured by Michel Dubreton and handed over to the British Army.
After being handed over to the British Army, Hakeswill faced execution. He was shot by a 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, perhaps after suffering a mental breakdown caused by the death of his mother at such an early age. One of his delusions being that his mother watched over and protected him from heaven, which caused him to believe he couldn't be killed. Hakeswill would also often talk aloud to his mother and at one point kept a portrait of an unrelated woman in his hat, which he also talked to.