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What I Watched Last Night: Undercover Boss (Churchill Downs Inc./Arlington Park)

By Thomas Chambers

Like Sugar Bombs being “part of a nutritious breakfast” or government EPA-rated mileage at 23 city/31 highway, things are usually not as they appear.
I simply don’t believe Churchill Downs Inc. (CDI) is the benevolent caretaker of horse racing and America’s biggest racing event. And I don’t believe reality television has much to do with reality. Instead, it’s a crass capitalization on the fact that Americans have an innate desire to believe what they see on television and in newspapers.
I didn’t make much inner progress on these things after watching the latest installment of CBS’s Undercover Boss, where the geek head of CDI went “undercover” to experience the “lowest” jobs in the company. You know, the other side of the tracks. The only bit of reality they shoot for and hit is that the employees they meet have eminently more grease in their elbows, work ethic in their brains and pride in their souls than any cookie-cutter, interchangeable MBA above them.


Noticeably absent from the show was any mention of the fans or horseplayers, or even a glimpse of the backside workers, whom some have compared to migrant workers. There wasn’t a Mexican groom or hot walker in the whole show. Maybe they figured Murrow had that covered back in 1960.
Meet William C. Carstanjen. Self-described as climbing up the ladder of corporate law and mergers and acquisitions, the corporate web site bills him as Executive Vice President and Chief Development Officer. Throughout the show, he is referred to as chief operating officer. We see him strolling into Churchill Downs, past the statue of Barbaro (figures) and into the boardroom to tell his “team” (godalmighty I hate that term and running into it here at the regular job) that he’s going undercover and they’d better keep it quiet.
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Questioning Reality 1: Are you telling me he didn’t have a Human Resources staffer scope out the employees at Calder Casino and Race Course in Florida and our very own Arlington Park beforehand to find the employees most likely to make this thing work?
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So he grows a few days’ worth of beard and says he’s Billy Johns. His movie company failed and he’s making a documentary about entry-level jobs. Hence, the cameras. And he’ll be staying at No-Tell Motels both in Florida and Illinois so as to not raise suspicion.
Leaving his truly sprawling estate in Kentucky “for a week,” his wife is quoted over the goodbye: “It will be interesting because Bill likes to be in control of things.” Ah, the true nature of any CEO. The ivory tower mentality is further driven home when Billy says, rather truthfully, “There’s a lot of responsibility in working in an environment where people have such a passion for what they’re doing.” Imagine that, caring about a job. That you have to have.
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Questioning Reality 2: Are Calder and Arlington really hiring? Wouldn’t you have to know someone to get in?
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Billy lands at Calder. He boasts of the $100 million investment CDI is putting into Calder. (It’s a casino and you’ll see their priorities by going to the Calder home page.
Billy goes to work for trainer Gillian Andreasen. I wonder if she ever wins a race because I could find no trace of her in the trainer standings. It appears she bops up and down the East Coast following the racing seasons, but she desperately needs to win a race or she may lose the few stalls she has at Calder.
All we really see here is Billy trying to feed the horses, which Gillian halts when his fear and apprehension of the horses starts to spook them. Gillian probably saved his life. “CDI COO Trampled by $5,000 Claimer” would not have looked good in the Daily Racing Form.
Striding across the apron to watch her horse race, Gillian tells Billy to not even think about working in this game, it’s dying and there are few if any opportunities. Billy’s real surprised at this. Man, doesn’t he read the trades? Holding the Check finishes badly and Gillian is angry, disappointed and fearful of the future. “When you’re down to your last couple of hundred bucks . . . ”
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Questioning Reality 3: Why on earth would Jean, the bugler at Arlington Park, allow this Gomer Pyle to even come close to her bugle, let alone have him attempt to actually blow the Call to the Post, without being ordered to do so by some Arlington big cheese? He actually did it and made Yoko Ono sound like Duke Ellington.
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Then he goes to work for Denise, whose job is to clean the Arlington luxury suites after the races. You’ve seen how many suites there are. It looks like Denise is the only employee doing it. Billy is bad and is slowing the process. Which is bad because it seems she’s part-time, at $8 per hour, and has to get it the hell done.
One of her biggest issues is that she commutes from Chicago to Arlington Heights, and the cherry-on-the-sundae insult is that nobody in security will escort her across a dark parking lot to her car. Denise is truly afraid for her safety.
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Questioning Reality 4: Yo, geek. Why do you ask so many questions?
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Still at Arlington, we meet Roxanne, a two-job employee who provides the evening’s comedy. In the mornings, she’s a backside worker, mucking stalls and washing horses. And damn, just as she tells Billy that he has to wash “any area there might be” on the horse, the camera cuts away. But I don’t think Billy got kicked in the head.
He’s giving her the third degree. “What do you want to be?” In a bit of great timing, “President of Churchill Downs would be fine.”
In the afternoon, Roxanne is the receptionist and Girl Friday in the press box. “People on the front side don’t get the people on the back side. I get to see both; it’s important,” Roxanne reveals. And, man, is that one, soo-weet press box? Although I didn’t see any wagering machines.
“That was an honest day’s work,” Billy moans as he flops on the bed that night.
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Questioning Reality 5: Is this guy really going to subsist on a 4.5-ounce microwaved cup of chicken noodle soup? Or did you do that just for the reality?
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His last job will be as a jockey’s valet (it’s really pronounced VAL-ett, like they do on the show, it really is). Being a team manager back in the day, I can relate. I can also see he’s going to fail miserably.
He’s hooked up with Kenny Rice, a former jockey who now sees to everything so all the jockey has to do is ride. He’s assigned to the vivacious Swede, Inez Karlsson, the only woman in the jockey colony. Inez reads the situation like she’s trying to split horses on the rail: “I’m a tough cookie. If I get pissed, I will tell you.”
While Kenny shows Billy his clipboard list of race and silks assignments, the one with the picture of a young girl affixed to the top, the boss keeps using the racing program. “Don’t use the program, it takes too much time to turn the pages.” Kenny points to the clipboard list with the picture of a young girl affixed to the top. “This is your bible.”
He’s supposed to tag along, but Billy loses track of Kenny and tries to find him. I wouldn’t be surprised if he went all the way up to the Million Room. The other valets are howling.
Inez won three races on the day, 10-1 on Two-Ninety Five in the one race we saw. Valets are not allowed to bet.
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Questioning Reality 6: If the music is so dramatic throughout these shows, how will we know when a scene really is dramatic? And do The Dramatics get a cut?
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Then we get hit with The Emotional Moment.
That picture on top of Kenny’s clipboard is an In Memoriam card for his teenage daughter, Meghan, who died of a heart condition just months previously. Billy starts bashing himself and then cries for not noticing it. I guess you can’t blame this deer in the headlights for not noticing.
Kenny’s always on the edge, but he seems to be handling it reasonably well. He really needs to be around the track and I would think being a valet has a lot of prestige in the world of the track. Probably a good idea to have him valet for Ms. Karlsson.
So it’s the moment of truth as William Carstanjen has to atone for his sins. He tells the CDI board that aside from the spreadsheets and stock quotations, they have to do their jobs on some sort of personal level, as dangerous as that might be. They look at him like he just landed from Mars with Baretta’s cockatoo on his wrist.
“Bill, how will you change the way you do things?”
“Understand that there is a personal level to these people and their jobs.”
I would have added: “And you’ll be manning the Miller Brewing ice cart in General Admission during Arlington Million Week.”
Gillian gets more stalls at Calder, and Denise takes a full-time job at Arlington, demurring his offer to take a job at a CDI facility (probably the Mud Bug OTB, Denise; good call) closer to home. He relocates Roxanne to Louisville to “work in the marketing department up to the Derby.” Seems like kind of a short promise, but we hope Roxie “takes the reins.”
And in what is probably one of the nicest gestures in racing, WC promises that Arlington will name a race for Meghan on Opening Day, April 29, 2010.
After showing a few clips from the show and telling the Arlington employees he’ll always remember them, Kenny gives him an arm knock: “You’re still gonna name that race for Meghan, right?”
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Questioning Reality 7: Does anybody really believe things will get substantially better for the people upon whose backs these companies profit? Why yes. Didn’t we just witness that on Undercover Boss?

Visit the What I Watched Last Night archives and see what else we’ve been watching.

Submissions and comments welcome.

1. From Sandy Thompson:
On Saturday, April 23, 2016, I watched Undercover Boss with Bill Carstanjen, COO of Churchill Downs. I always enjoy watching Undercover Boss.
This show in particular however, was a little disheartening when Mr. Carstanjen at the end of the show met with the people he worked with and did not offer any money to them.
It was very nice to see some were offered full-time work, and an upgrade in positions. It would have been really great if Mr. Carstanjen would have offered them cash as well.
Now you know Churchill Downs makes millions of dollars and it was unbelievable to me that they are so cheap not to have given cash to these people.
I have watched enough Undercover Boss shows to see that most all were extremely generous in helping the people they worked with get a college education, buy homes, cars, college funds for their children and lots of cash. Mr. Carstanjen, really? Is your
organization that hard-up not to have been more generous? Your organization is extremely cheap and that doesn’t speak well for you or your board.

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Posted on March 18, 2010