Bookmaker Spotlight: Rivers’ Kyle Wainscott Discusses Career Path to the Sportsbook

Kyle Wainscott, sportsbook manager at Rivers Casino in Des Plaines, Illinois, and winner of the Bookies Battle 2022 second-quarter mini-contest, was gracious enough to take time to answer questions about his career progression and personal betting approach, as well as offer advice to prospective sports betting industry professionals.

‘Trust Your Gut’

Would you believe that Wainscott took first-place honors in our second-quarter contest (covering NFL Weeks 6-9) with a ‘less is more’ approach? He’s the sports betting version of your friend who aced every exam despite appearing to be under-prepared.

“I don’t do a lot of studying,” admitted Wainscott. “Personally, I feel like if I fixate on player stats or team stats, I end up overthinking it and making a bad choice because of what the numbers say should happen. I watch enough football to have an opinion on how a team is performing, and if I’ve learned anything this year, it’s best to trust your gut and go with it.”

Watching a lot of sports is a great start to betting success. And a childhood shaped by playing baseball, football, lacrosse, and basketball, plus frequent weekends at the Arlington Racetrack, influenced Wainscott’s interests and served as the foundation upon which he set his career path.

‘Jumped at Chance’ to Join Sportsbook

Wainscott began as a Security Supervisor at Des Plaines’ Rivers Casino before advancing to Customer Service Manager and, most recently, to Sportsbook Manager. Getting his foot in the door was only the beginning of his journey.

“As soon as discussion started about the state of Illinois legalizing sports wagering, I knew I wanted to be a part of it and I jumped at the chance,” he said. “I was excited to join this property shortly after it opened. The prospect of getting in early and working my way up throughout the company was something I was eager to pursue.”

It’s natural to see someone in Wainscott’s position and consider his situation to be an ideal scenario. However, Wainscott wasn’t spared the difficulties associated with the COVID-19 pandemic.

“The COVID-19 pandemic was the most challenging thing I’ve faced,” Wainscott recalls. “We closed six days after the sportsbook launched. To go from opening the first sportsbook in Illinois right before March Madness to seeing the doors get shut was a roller coaster of emotions.”

It’s not difficult to empathize with the sharp emotional swings Wainscott endured. What doesn’t kill you makes you stronger though, right?

“Since then, I don’t view many things as a challenge anymore. They are just hurdles that we have to find a reasonable solution to,” explains Wainscott.

Sports Betting Brings People Together

It’s easy to sense Wainscott’s appreciation for the relationships he’s nurtured and developed — both throughout his tenure at Rivers Casino and his personal sports betting experience.

“There are friends that I don’t get to see often or talk to on a regular basis, that I get to communicate with more now because of sports wagering,” he said. “Everyone wants to talk about who they like this weekend or a same-game parlay they hit last week. It’s definitely a positive in my opinion.”

Wainscott’s experience in this context is not different from what millions of people across the globe experience with fantasy sports. Sports betting certainly has the potential to promote social interaction as it continues to evolve as a mainstream activity.

Relationship-building stands as one of Wainscott’s professional passions as well.

“The people I work with are my favorite thing about my job,” he said. “I’m blessed to be surrounded by an excellent leadership team here at Rivers Casino in addition to the sportsbook team that we have put together. When people are enthusiastic about what they do and genuinely care about each other, it makes the experience so much more enjoyable than just a job.”

Wainscott continued, offering advice that prospective sports betting industry professionals can utilize. (It’s actually great advice for all professionals.)

“Respect is everything in this industry. Treat your team members and customers with the utmost respect, and you will be successful. Consistently treating each and every person you come in contact with, with respect will only lead to positive outcomes.”

Success, whether personal or professional, starts with an intrinsic drive to improve oneself and strive for new heights. It’s evident interacting with Wainscott that he possesses many of the key attributes necessary for reaching personal heights.

Positive Outlook for the Bears

… Now, if only Wainscott’s Chicago Bears could climb what looks like an NFC North division in transition.

“The Bears will go as far as Justin Fields takes them,” he remarked. “He is the most dynamic runner (for a QB) I’ve seen since Michael Vick, so I like our chances moving forward. It doesn’t hurt to have $100+ million available for free agency either.”

Second-Quarter Winner

With a 36-18 ATS record in Weeks 6-9, Wainscott won the 2Q mini-contest of Bookies Battle by two games, ahead of second-place finishers Michael Hastey (DraftKings at Casino Queen) and Craig Steppach (Gold Strike). He collects $500 for the win and earns a spot in the playoff portion of the contest, where there’s another $2,000 at stake.

Wainscott also holds the lead in the season standings.

Bookies Battle is an NFL picks contest among bookmakers throughout the sports betting industry. Follow along with contest and see who the experts are picking this week right here.

Bookmaker Spotlight Q&AsBaldini’s Robert Kowalski | South Point’s Chris Andrews | BetMGM’s Jason Scott | Bally Bet’s Jay Rood Westgate Young Gun Casey Degnon | Golden Nugget’s Tony Miller

About the Author
Craig Williams

Craig Williams

Craig Williams is a Charlotte-based writer for Gaming Today, who has worked professionally in the gaming, fantasy sports, and sports business industries. He’s an avid fantasy football player, managing over 100 leagues across multiple formats. When he’s not pouring over Vegas odds and statistics, he’s indulging in soccer and enjoys anything from LigaMX to Champions League.

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