Undercover Boss: President of Churchill Downs | Where are They Now?

Bill Carstanjen, Chief Operating Officer of Churchill Downs (the home of the Kentucky Derby), trades in his slick suit for t-shirt and jeans to appear on Undercover Boss

Churchills Downs, better known as the home of the Kentucky Derby, sent their then-COO (Chief Operating Officer) Bill Carstanjen, to go undercover to work along the company’s staff and horses to get a better look at how the $500,000,000 company is run. 

“I like to watch them from afar.” 

Carstanjen shares that while he is passionate about his business of running Churchill Downs, the home of the Kentucky Derby since 1875, he has not been on a horse in over 15 years. He also mentions that his job is handling a legacy that is steeped in tradition, but as a person who is in charge of making sure the business is profitable, he must sometimes step on those traditions. These changes are not always welcome, and he is going undercover as Billy Johns to get a feel for how these changes are being received by everyone down near the tracks. 

His backstory as Billy Johns is that he used to own a moving company that has gone out of business, and he is exploring entry-level positions at Churchill Downs while a camera crew documents his journey. 

Job #1 - Horse Training at Calder Race Course - Miami, FL

His first stop has him flying down to Calder Race Course in Miami, FL, to meet Gillie, a horse trainer. He is put face-to-face with the horses, and is instructed to make their food and dive into the horse pens to feed them. 

During a routine equipment cleaning, Carstanjen learns that Gillie pays for the horses’ feed out of her own pocket. She is left with a few hundred dollars at the end of the month to pay for her family’s food, car and more. She ultimately recommends that Carstanjen, or Billy John, NOT get into the business of horse training. 

Job #2 - Bugler - Arlington Park Racetrack - Arlington Park, IL

Next stop, Bill Carstanjen is flown out to Arlington Park, IL, to work at the Arlington Park Racetrack as a bugler. No race starts without the blare of the bugle at any of their racetracks. As practice, he is asked to practice on a kazoo, which turns out to be disastrous. No surprise here as Bill proclaims that he is not musical at all!

Job #3 - Cleaner - Arlington Park Racetrack - Arlington Park, IL

One of the core pillars of the business at Arlington Park Racetrack is the availability of luxury suites. After the parties leave, the cleaning crew stays late into the evening to scrub down the spaces and be ready for the next group of guests. He is paired up with Denise, and she shows him the ropes of how to properly clean the suites. After watching him scrub down tables and vacuum, she shares with the audience that Billy would probably not be hired as he is too slow. 

She shares that she is only paid $8/hour, and she often ends work at midnight. In addition, she divulges that she is afraid to walk across the dark parking lot by herself once her shift ends. There is not enough security to make her feel safe before her 90 minute drive home. 

Job #4 - Backfill - Arlington Park Racetrack - Arlington Park, IL

Carstanjen continues his mission at Arlington Park Racetrack and meets Roxanne, who is a backstretch employee. Her duties include washing the horses down at the end of the day. While on the job, she divulges to Bill Carstanjen that she hopes to become president of Churchill Downs one day! 

Job #5 - Jockey’s Valet (Assistant) - Arlington Park Racetrack - Arlington Park, IL

Carstanjen is then paired up with Kenny, who is a Jockey’s Valet. This is the person who preps EVERYTHING for the racers, making sure they are ready to hop on their horses and race down the tracks. This may be the most fast-paced job at the track, and Kenny has Carstanjen running around gathering supplies and clothing. In one of the most stressful moments of the show, Kenny and Carstanjen are separated as the race is about to start. 

As they sit down to debrief on the events of the day, he learns that Kenny’s daughter passed away recently from a heart issue, bringing Carstanjen to tears. 

The Big Reveal

Bill Carstanjen returns to the corporate office, and immediately calls for a meeting with his senior leadership to address all of the issues he uncovered while working the tracks. 

Bill brings in each of the people he has worked with during his undercover stint, and this is how each of those meetings went. 

Gillian
Bill Carstanjen is so moved by Gillian’s dedication to her job, he offers her more stalls to manage, and offers her a full-time job at the track. 

Denise
Carstanjen was very concerned by Denise’s dangerous walk across a parking lot, and has started a program to provide security escorts to all staff working late at night. In addition, to address her 90 minute commute to Arlington Park, he offers her a job at one of the betting parlors closer to her home. 

Roxanne
Carstanjen was so impressed with Roxanne’s drive that he offered her a job in the marketing department at Churchill Downs. 

Kenny
Carstanjen was most moved by Kenny’s story, and decides to name a race in honor of Kenny’s daughter. 

Where is Bill Carstanjen, Chief Operating Officer of Churchill Downs, now?

Bill Carstanjen is STILL with Churchill Downs, and has since moved up the ranks and is now the Chief Executive Officer of the company.  

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