LOUISVILLE, Ky. (WDRB) -- Think it's difficult placing a bet? Try taking thousands.

And do it for half a century. 

While hundreds of new tellers are trained every year for the Kentucky Oaks and Kentucky Derby, the man who oversees all of their windows is celebrating a big milestone. 

Today is Jim Kessinger's 50th derby.

"I told my family I was going to quit ten years ago. So, they did a 40th party for me. I didn't do it. I just kept on working," Kessinger said.

Behind each of the 14 races on derby day is a whole lot of dollar signs. "It's not unusual for me to have 30, 40, 50 thousand dollars by the third race," says Denise Richards, Mutuel Teller for Churchill Downs.

Around $200 million will be wagered in total. "It's a part of the track that nobody really thinks about," says Debra Humphrey, Mutuel Clerk.

Each of the 1,035 betting windows at Churchill Downs has someone who is pretty good in math and stays calm under pressure.

At least they better be. 

"If they [tellers] don't know what they're doing and they end up shorting their money box, it comes out of their paycheck," Richards said. We've had people that end up owing Churchill Downs when they've worked two days."

Richards and a team head up training for about 300 people every year who have never worked the terminals.

The tellers will be trained in how to punch a bet and handle money.

Richards reminds the derby first timers that it's dollar amount, bet type and horse number.

"That's one of the hardest parts is being a mind reader and figuring out what the customer actually wants.," Richards said. 

It's a four hour class to handle any bet, no matter how big or small. "I used to work Millionaires Row. Most of those people, the celebrities are here more to be seen than they are to bet big money. You probably have bigger betters down here in the common areas," Richards said.

Richards would know. "This will be my 41st derby, and I haven't missed a year," she said.

Not quite as impressive as Kessinger, whose office backs up to the Twin Spires. It's where he keeps the supplies for every betting window. 

The former vice principal and football coach started taking bets for a little extra money for his now wife of 50 years and kids.

He now personally makes sure every window is set. "I've been in all of those 77 spots. It's right here. I know every nook and cranny in this race track," Kessinger said.

Kessinger isn't slowing down after 50 years. "It's gotten to be a really fun job. It's not the money anymore. It's just going some place where somebody knows your name. It's kind of fun, being that old, 'hey Jim!' I know everybody on the track," Kessinger said.

The betting window is home for him and maybe one day, to the new class of tellers.

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