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Undercover Boss: Churchill Downs

March 14, 2010 07:46 PM by Nancy Floyd

UNDERCOVER BOSSOn an all-new episode of Undercover Boss on CBS, viewers are taken undercover into Churchill Downs, host of the Kentucky Derby. Churchill Downs COO, Bill Carstanjen is going undercover in his own company to see what life is really like for his employees. Keep reading for more details on his experience cleaning race suites, bathing horses, and running errands for jockeys…

Tonight on on CBS, Undercover Boss is going behind-the-scenes at Churchill Downs as COO, Bill Carstanjen, trades in his white collar for a blue one to work among his workforce. The first thing we learn about Bill Carstanjen, the guy running the largest horse racing business in the world? He’s afraid of horses! After the prerequisite shots of Bill interacting with his family and an executive meeting where the board members pretend to be shocked to learn about Undercover Boss, Bill leaves behind his fancy Louisville office and McMansion for Calder Race Course in Miami, Florida.

Bill’s first day as the Undercover Boss starts at 6am and he’s a little nervous about being recognized. Fear not…his stellar disguise (which includes contact lenses and not shaving for a day) should keep him safe even though he was just at this facility a few months ago. Uhh, unlikely, but we’ll go with it. Today, Bill’s working with a horse trainer named Gillian. Bill’s first task? Feeding the horses. I’m pretty sure he comes dangerously close to wetting himself. Bill helps Gillian hose down the horses and clean the bridles as they “casually discuss” the working conditions for horse trainers. It turns out it’s not so good.

As a trainer, Gillian makes 10% of any money her horses win in races. Financially strained, she needs one of her horses to win in today’s race. Bill is there to cheer on Gillian’s horse, aptly named “Holding the Check”, but there’s no cash prize to take home today.


Bill’s second day as the Undercover Boss is at Arlington Park Racetrack in Illinois and he’s about to become a bugle boy! Bill will be learning how to play the “Call to Post” from Jean, the Arlington Park Bugler. This genius can’t even figure out how to play the kazoo. After his brief lesson, Bill is terrified to play in front of the crowds. Is there anything this guy isn’t afraid of?! His bugle-playing skills are atrocious, but Bill is quite proud of himself for reasons unbeknownst to me.

Bill’s third job on Undercover Boss is cleaning the suites at the Arlington Park racetrack. Bill clearly has a maid, as evidenced by his lack of knowledge on how to turn on a vacuum. Bill and his makeshift boss, Denise, are responsible for cleaning two floors of the massive building. As they work, Denise has no issue airing her grievances with a total stranger. She quickly lets Bill know that her pay sucks, she feels unsafe walking through the dark parking lot at night, and she has a 90-minute commute to/from work.

UNDERCOVER BOSSBill’s fourth job undercover is on the backstretch of Arlington Park racetrack working with a spunky young woman named Roxanne. As they work together to bathe a horse, Bill quizzes Roxanne about her future plans since she’s a new employee of Churchill Downs. Her goals include running the whole company! Sounds like a good idea to me since Bill is clearly a total chump and should be replaced. Bill meets up with a cleaned-up Roxanne in the press box where she works as the press box operator. Working two totally different jobs is all just part of her master plan to take over Churchill Downs.


Bill’s fifth and final job as the Undercover Boss is as a Jockey’s valet alongside Kenny. This is a fantastic job for anyone dealing with height insecurities. Bill looks like a giant! He should be deemed King of the Jockeys. Bill will be working with Inez, a sassy little jockey who isn’t afraid to tell it like it is. Bill scurries around after Kenny looking for Inez’s uniforms, helmets, and goggles all of which is organized on Kenny’s handy dandy clipboard. After a busy day (which includes three wins for Inez), Kenny and Bill sit down for the required Undercover Boss heart-to-heart. Kenny pulls his daughter’s photo from the front of his clipboard and tells Bill that she passed away a few months prior. Bill is moved to tears as he realized that he’d been staring at her ‘in memoriam’ picture all day long and never bothered to notice.

After finishing the week, Bill meets with his executive team to talk about all the ways his experience on Undercover Boss has made him a better man. Now it’s time for Bill to reveal his true identity to the employees he worked with earlier in the week. Naturally, everyone is shocked to learn he’s the COO of Churchill Downs (or at least pretend to be). Bill admired Gillian’s determination and wants to reward her with three new stalls and a full-time job at the track if she wants it. Denise is given a job transfer to a track closer to her home, as well as a new Churchill Downs’ policy that allows employees to be escorted to their cars by security at night. Score. Bill offers Roxanne a marketing job at Churchill Downs and she’s “super stoked” about it. Lastly, Bill meets with Kenny and invites him to present the winning trophy at a special race named after his daughter.  Last, but not least, Bill addresses the employees of Churchill Downs at a company-wide event, shows a lame highlight reel, and talks about what a changed man he’s become. Applause, applause!

Tune in next week to Undercover Boss when the young CEO of GSI Commerce goes undercover in his e-commerce company.

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Photos Courtesy of CBS

Topics: CBS Reality TV Shows, Undercover Boss |

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