Josh Pearl
Josh Pearl — an Evans Scholar — is now Director of Sportsbook Operations for Penn Interactive Ventures, the online division of Penn National Gaming.

Josh Pearl has always loved the challenge of competition, starting at an early age with sports and Pokemon card tournaments. But when a friend who suggested there might be something more fun to do with his time, Pearl found himself in an occupation that not only helped pay his way through college, but led him to a career that stokes his competitive fires every day.

Pearl is Director of Sportsbook Operations for Penn Interactive Ventures, the online division of Penn National Gaming. The corporation operates more than three dozen casinos and racetracks throughout the country, in addition to its online division.

The pursuit that changed Pearl’s life? Caddie class at Old Warson Country Club in St. Louis.

“I used to play Pokemon cards and there was a store in town that used to have tournaments all the time,” Pearl said in a recent phone interview. “So, there was a kid that I became friends with. He lived in what I would say was a more affluent part of town, and he said, ‘I can’t play Pokemon on Monday because I’m going to caddie class.’ And I said, ‘Caddie class? Is that something you have to be invited to?’ and he said no.

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“So, I asked to tag along, went to the caddie class and I guess the rest is history.”

Old Warson is a Robert Trent Jones Sr. original design, opened in the spring of 1954 and host to the 1971 Ryder Cup: the final time Arnold Palmer, Jack Nicklaus and Lee Trevino all played together on the United States squad, and Palmer’s final Ryder Cup appearance.

The course also hosted the 1957 Western Amateur, which featured Charles “Chick” Evans, the founder of the Evans Scholar Program that offered a full scholarship to Pearl. One of the most famous members of Old Warson is three-time U.S. Open Champion Hale Irwin, who began playing there during his junior golf days.

Pearl may be a bit biased, but in his opinion, Old Warson is better than Bellerive — the older, more-celebrated rival in the Gateway to the West.

“A lot of people will tell you it’s the best course in St. Louis,” he said. “It’s not as long as Bellerive and it doesn’t have the space to hold a large capacity. But a lot of people will tell you it’s got the best mix and is as challenging as Bellerive.”

Josh Pearl
Josh Pearl never could have known the opportunities he’d have in life by tagging along to a caddie class.

Not long after Pearl started caddying, he learned one lesson the hard way, one that’s stuck with him ever since. It also resulted in an interesting and successful partnership with one of Missouri’s top amateur golfers.

“I was about 13 and they held a big local tournament for amateurs there,” Pearl said. “The gentleman whom I caddied for, I accidentally touched the green with the flagstick. His opponent in match play did not call it, but he called it on himself. I was devastated for costing him the hole but there were two things I learned from that: the value of honesty and accepting the mistakes that you made.”

The opponent that day was Skip Berkmeyer, three-time Missouri Golf Association State Champion. The list of winners includes such notables as Tom Watson and Payne Stewart. Berkmeyer is also a five-time winner of the Old Marson Cup for match play and holds multiple other amateur titles. Pearl wound up caddying for Berkmeyer for the next five years after his gaffe.

It’s hard to imagine summers in St. Louis without the voice of the legendary Jack Buck ringing across the airwaves. The longtime St. Louis Cardinals announcer passed down those famous vocal cords to son Joe, the lead announcer for all of Fox Sports’ major televised events, including the U.S. Open.

“I was fortunate to caddie for Joe Buck quite a lot, and even several times with Troy Aikman, when Joe would bring him out,” he said. “I’ve had some awesome experiences.”

During his 10 years as a caddie at Old Warson, Pearl learned more than just how to carry a bag. He learned how to read people, a talent that comes in handy when he’s dealing with federal rules and regulations and the people in his industry.

“The people skills that you build are probably more valuable, I think, longer term than anything else,” Pearl said. “Just the way that you learn to read people, the way that you see people treat others, in good ways and bad ways.

“You’re often around affluent people but people also treat their status in life in different ways, so I think you see all different walks of life. Some people inherited money, while others made it themselves, people who have worked their way up the chain to executive roles, people who don’t treat people well, people who treat people like they’re part of their families.

“It’s a really interesting dynamic and it gives you a pretty good foundation for life.”

Pearl was an Evans Scholar at the University of Missouri in Columbia, majoring in business with emphasis in finance in 2010. In addition to caddying as a young teen, he also loved going to the local horse track (Fairmount Park) with his father. That led him to pursue a career that combined his business acumen with his competitive nature.

And yes, the movie “Caddyshack” was true to life in at least one respect.

“I just kind of fell in love with horse racing,” Pearl said. “As someone who knows caddies pretty well, there’s a lot of friendly gambling that goes around in the caddie house, whether that be in the form of playing gin or poker, or just out on the course.”

Pearl found himself in investment banking after school, then landed a job at a startup online gambling company just outside of St. Louis. While he was back in the banking business, he reached out to Penn Interactive and found the perfect job for his competitive nature.

“I searched around and found an opportunity to run the online horse racing product,” Pearl said. “It’s the largest form of legal online gambling in the U.S., which dates back to about 2000. So getting the job with Penn Interactive, that was my foot in the door. I’ve been fortunate to be able to assist with a good amount of government and regulatory affairs as far as online gaming and sports betting goes, and have been working on getting some other very cool forms of online gambling up and running.

“To be working for a great company like Penn National Gaming who has a presence in so many states, there isn’t a better opportunity, or a better time to be in the business.”

As an Evans Scholar alumnus, one of Pearl’s favorite moments was helping with the pro-am event at the BMW Tournament at Bellevrive, a PGA Tour event that donates a portion of the proceeds to the Evans Scholar program.

Pearl not only got to participate as a caddie, he got to meet two of his favorite golfers and their loopers, too.

“That was probably one of the cooler experiences of my entire life,” he said. “As part of [the Evans Scholars], we were asked to go caddie that day. I had caddied for a member of Old Warson whose company had paid for his pro-am spot. We had Steve Marino in our group.

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“I got to walk wherever I wanted to. I could walk in the clubhouse and even the locker room . I was having a great time with him and his caddie. Just real fun guys, didn’t take anything serious at all. I think it was I owe him five bucks if he made birdie, if he made par no one won the hole, if he made bogey I won five bucks. I think I ended up with five bucks.

“On top of that, I got to meet Phil Mickelson as he was walking back to his car. Bones [Mackay] was with him and I probably got to talk with him for five minutes. Brandt Snedeker is my other favorite golfer and I got to talk with him for probably 10 minutes. Nobody else around. It was surreal.”

Pearl played to a 5- or 6-handicap himself in his younger days, although business has taken away from his ability to spend time on the course. He still feeds that competitive fire with softball, racquetball and indoor soccer. But golf is never far from his mind.

“As business has taken over more of my life and focus, I don’t play as much any more,” he said. “Hopefully, once I’ve achieved what I want in life and hopefully join Old Warson Country Club and have a caddie of my own, I hope to pick it back up.”

When Pearl thinks back on his days as a caddie, he realizes that one of the most fun things about the job was the variety and the uniqueness of the experience. It’s no surprise that Pearl’s brother, Luke, and sister, Hailey, have carried on the family tradition by caddying at Old Warson. In fact, Hailey is also an Evans Scholar, in her sophomore year at Mizzou.

“No loop is ever the same,” Pearl said. “You may caddie for the same person every Saturday and they may request you but it’s always different.

“There are people out there who want all the help in the world, other people want no help. You have people who are really good players, you have people who really are not good players. You have people out there playing with their families, you have people out there maybe trying to close a multi-billion dollar deal.”

That ability to understand the environment and ability to adapt to different situations is something Pearl uses all the time in his career.

“In business, there are a lot of different scenarios, different types of personalities you have to deal with,” he said. “So for me, I’ve facilitated assisting on the governmental relations, and that’s just Level 2 of caddying. It’s different, but you’re able to understand your audience and be able to articulate things in the appropriate manner.”

Whatever the future of online gambling may be, Josh Pearl is thrilled to be in the thick of it. It’s part of his competitive nature that goes all the way back to his Pokemon card playing, and that one time he decided to follow his friend out to the golf course.

The Evans Scholars Program provides academic, professional and social resources that help students maintain a cumulative 3.3 GPA and 95 percent graduation rate. There are a record 985 Evans Scholars enrolled in 18 leading universities for the 2018-19 academic year, and more than 10,830 young men and women have graduated as Evans Scholars since 1930. For more information, visit https://wgaesf.org.