As the years passed, both Chester and Bruce became ensnared with a certain girl, along with half the town's young population. Dot was considered the prettiest gal in the area, and Chester was more than a little surprised when she chose him out of everyone to both flirt with and later date. He was wrapped around her finger from the very first moment, and gave her everything she could ever want, no matter the cost to himself. They had begun to talk of marriage, when Chester suffered a bad accident from a rodeo ride gone wrong. He shattered the bone in his hind left leg and was in a serious coma with head trauma for almost seven months. The doctors had little hope of him ever being able to walk again, let alone wake up, but the stubborn bison somehow managed to pull through, and surprised everyone by being relatively okay. The bone didn't heal quite right, but after months of therapy, he could walk again, albeit with a heavy limp. The worst thing, though, was waking up to find that Dot had moved on with Bruce of all people, and his ex-friend almost bragged that she'd been seeing him since before the accident. She was heavily pregnant when Chester came back to, and after the birth it was revealed that the child was a little bison girl, and clearly not Bruce's child. The man was more than pissed about it and forbade Chester from having contact with her, quickly moving both himself and Dot to the other side of the town.

Chester spent the next six years re-learning how to do tasks he'd used to find simple, including ranching. He tried in vain to reestablish contact with Dot and Bruce, but the possessive man had shut him out of their lives, and losing both his best friend and his girlfriend (and most importantly, his daughter) was a blow he didn't know could hurt as bad as it did. When the news that his biological father had passed away and left the large company he ran in the city to his children, Chester was the only one that had any interest in taking it over, both the best with numbers in his family and now the most useless with ranch work. Packing a bag, he bid his family goodbye and set off for a new life in the city.

Arriving in the city, the bison was more than a little under-prepared for just how different life in the city was to that of his tiny, country hometown. He quickly took over his father's company, much to the chagrin of the boardmembers who didn't want to deal with an inexperienced country boy as their boss. Chester never faltered, though, and proved himself to be both a fast learner and willing to show he had what it took to adapt to his new changes. With the help of the chairmen and a few particular boardmembers that were willing to give him a chance, Chester learned to navigate the ropes of business life. Though he's proven himself to be strong CEO-material several times over, some of the senior boardmembers are still reluctant to see him take the reins of the company in full. The fact that he still harnesses his inner child and has pulled off several pranks, mostly on said senior members, likely doesn't help matters, but he finds a deskjob to be stuffy and boring as hell. In addition to that, he can oftentimes be found helping out around the premise, whether it's lawnwork or helping change lightbulbs and fix a leaky faucet. This gets on some of the board's nerves, saying that the boss shouldn't be doing grunt work, while others find it admirable and a better reflection of the company. Either way, Chester doesn't care what they think, mostly doing the odd jobs to get himself out of his office chair and his hands dirty.

Though Chester still has yet to officially claim the title of CEO, he is the boss of the company in all but name, and relies heavily on his board for support and suggestions. With his work, the bison managed to both set up a trade arrangement and finalize it with a sister company, making his business essentially the largest importer and distribution warehouse for frozen and fresh meats and other farm products in the region, and his family is proud of him for being able to make something of his life despite his setbacks. Though Chester doesn't admit it, he shares that pride, having been close to giving up completely during his therapy. Despite now living and working in the city, Chester never changed from his cowboy getup, and though his employees eventually got used to it, he's more than used to the funny looks he gets on the streets. Chester goes back home for every major holiday and family get-together, and loves to explore the city in his free time, even going to cheesy tourist destinations. Overall, he's happy to be where he is in his life, and more than ready to see what comes next.

Mabel, 60 (Mother): Chester loves her dearly. He brings her back knick knacks from the big city, and although she pretends to be cranky about "unnecessary clutter" he knows she secretly loves them and keeps them all on display in the living room. He jokes that her gossip about the ladies in town is the bread and butter of their relationship.

Austin, 62 (Father): Deceased. Has very few memories of the man, and is pretty neutral about him.

Blake, 58 (Step-Father): On pretty decent terms with. Definitely views the man as a father figure, and looks to him for both support and approval.

Weston, 45 (Older Brother): On good terms. Still horses around with him when home for the holidays, and helps out with caring for the ranch when he gets the chance.

Shiloh, 39 (Older Sister): On good terms. She was the one who taught him how to be a rodeo bull, and helped him learn to rope as well.

Colton, 32 (Older Step-Brother): On pretty bad terms. He was always a bit rude to Chester, even when they first met, and Chester could never figure out why. After the rodeo accident, though, Colton claimed that Chester was useless and should be kicked off the ranch altogether, which hurt a good bit.

Sawyer, 27 (Younger Brother): On great terms. Pretty much his best friend now, along with Presley. They got into all sorts of trouble when they were younger, and love to reminisce about their shenanigans at family get-togethers.

Presley, 23 (Younger Step-Sister): On great terms. He dotes on his little sister, and practically raised her. She's the one he writes to and calls most often.

Dakota, 8 (Daughter): Chester doesn't get to see her much since he doesn't have custody of her, but he loves her more than anything and strives to be the best father he can to her.