Will Jackson was once a loyal soldier at Stormholt living with his son and his wife Jeanne. He met her under an old oak tree in her father's field as she fought off a wild dog. He used to jump over a creek behind their barn with his son, who can never jump across due to his height. As Jackson told him this, his son kept doing so for a month until he finally succeeded. That day was Jackson's proudest moment.
He served the Crown hoping that his family would be taken cared of in exchange. However, when Luther Nevrakis usurped control over Stormholt, Jackson's family died of starvation and he left to fend for himself by joining a group of mercenaries led by Severin, discarding his honor but still retaining some discipline. He vowed to fight for nobody but himself.
At one point in time, Severin secretly made a personal deal with Nevrakis soldiers, and upon their approach, he witnessed Leon Stirling handle them himself drunk and with only a broken chair leg. At this point, he already met Val.
Will has brown eyes, brown neatly-combed hair and a brown full beard. He wears the standard Stormholt foot soldier armor consisting of a silver breastplate and shoulder guards held by brown belts and fasteners, and silver mesh armor covering the upper arms. In addition, he wears blue sleeves underneath, brown elbow gloves, and a blue cape.
Jackson is a very loyal soldier and a strong fighter. He once disdained the idea of fighting for royalty as he believed kings and queens do not keep their promises at all. He confessed to Gabriel that had lost his honor, and now served himself; he was willing to gamble his life for money only, like a typical mercenary. He however kept his discipline, unwilling to live like wild animals as the mercenaries did.
Jackson is shown to be remorseful of his actions, openly displaying humility to Kenna after he unknowingly mistreated her upon their first encounter, unlike Val. He is a dutiful soldier, marching, upon Kenna's orders, on his own from the Five Kingdoms all the way to the Blackspine Mountains and back to Lykos, all just to inform Dominic Hunter that Kenna wants him to come back for battle.
Jackson is also discriminatory against former enemies, refusing to hide his hatred of the Nevrakis to Diavolos despite the latter trying to act cordial. He is also equally hostile to what he deems as former allies, as he did not hesitate to execute Raydan upon meeting him following his alleged defection to Azura.
Will becomes impressed by Kenna after he betted on her and she wins the knife toss game between himself, Kenna, and Val. His respect for her grows once he realizes she is the Queen of Stormholt, which Val attributes to his desire to serve others.
Should Kenna partake in the mercenaries' merriment, Jackson will give his full and undying loyalty to her. In Book 1 Chapter 15, he is seen constantly worrying about Kenna throughout their reclamation of Stormholt. He becomes overprotective, even more so than Gabriel, ferociously murdering all Nevrakis soldiers trying to attack her, not letting any even lay a finger on her.
Their friendship continues to strengthen, and after Leon's death in Book 3 and his appointment as Crown Guardian, Jackson was fiercely devoted to his duty, furiously defending Kenna when Luther bickered with her in the dungeon, and motioned to unsheathe his sword during Kenna's wedding after he asked if there were anyone opposing the marriage. He again became almost as overprotective as Gabriel especially after Kenna's marriage.
Will respects Leon as one of his superiors, both in the Mercenary Camp and in Kenna's army.
Val has a playful relationship with Will. She constantly teases him due to his background as a trained soldier, and for his instant respect and submission to Kenna.
Jackson has a crush on Dom, revealed in Book 3. The player can choose to pursue the relationship for 19 diamonds.
- Will's character model was later retooled for Seth and Cid.
- In Book 3 Chapter 14, after drinking with Dom, Jackson mournfully reveals that Kenna's battle with Azura would fall on his son's twelfth birthday.
- Will is the only character in The Crown & The Flame series never to be referred by his first name; he is referred to only by his last name.
- A character who has the same look makes an appearance in a flashback in Bloodbound, Book 1, Chapter 5.