On Sunday, CBS's (CBS) Undercover Boss took a turn around the track with Bill Carstanjen, COO of Churchill Downs (CHDN). As the University of California–Berkeley and Columbia–educated Carstanjen cared for horses, helped dress a jockey, and tried his hand at the bugle, the show gave viewers an in-depth look at the inside workings of the horse-racing world.

Churchill Downs is generally associated with the Louisville track that bears its name, but the company's holdings extend far beyond Kentucky -- including other tracks, off-track betting parlors, and horse-racing TV networks. For his glimpse at how the other half lives, Carstanjen worked at two Churchill Downs properties, Arlington Park outside Chicago and Calder Horse Park in Miami.

At Churchill Downs, there's a deep internal division between the "front office" folk, who make most of the decisions but have minimal racing experience, and the "back-side" workers, who have a deep passion for the sport. Carstanjen fits firmly into the first group. He came to Churchill Downs from General Electric (GE), where he was general counsel and managing director for the company's commercial finance–energy financial services division. While his background prepared him for a job in the Churchill Downs head office, it didn't give him an understanding of the gritty realities of its workers, a void he hoped to fill with his week-long stint on the show.

The Future's So Bright

While some previous "undercover bosses" threw themselves wholeheartedly into their entry-level jobs, Carstanjen is far less engaged -- in fact, three of his five supervisors question his effectiveness and work ethic. Gillian, a horse trainer and his first coworker, notes his skittishness with the horses and his seeming inability to complete the tasks she gives him. After he soaks Gillian while bathing a horse, she tells the camera crew, "Right now, Bill's future is not looking the greatest. He just has a lot to learn."

At Arlington Park, Carstanjen works the night shift with Denise, an $8-per-hour employee who commutes 90 minutes to clean luxury suites. After showing Carstanjen the ropes, Denise grows visibly agitated at his slow, awkward progress: "Billy wouldn't be good at this. He's just not cleaning material. He's slowing me down tremendously."

Carstanjen's inefficiency becomes an even bigger problem when he works with Kenny, a jockey's valet. The undercover boss is quickly overwhelmed by the quick pace of the job, and ultimately, his supervisor has to give up on educating him, choosing instead to simply tell the hapless exec every single thing he needs to do. Later, when Carstanjen wanders off in search of Kenny, both become useless as they spend minutes wandering around in search of each other.

Of course, there are also up moments. In his second job, blowing the bugle, Carstanjen's painful fumbling offers comic relief. His total lack of musical experience, paired with disturbingly insufficient training, yields a bugle call that could best be described as tragic.

Later, he shadows Roxanne, a perky, ambitious employee who works in both the front and back ends of the company -- a position that reveals to viewers that Churchill Downs's front and back end needn't fight each other. Unfortunately, this handy moral is only surprising to Carstanjen, who seems incapable of personal reflection.

Grunts: They're Just Like Us!

After five episodes, Undercover Boss seems to have found its groove (or rut, depending on your perspective). Every episode presents a front-office suit who fumbles around at a few entry-level jobs, discovers that -- surprise! -- his employees are humans, explains his obvious revelations to a boardroom full of other suits, and makes the dreams of a few select employees come true. In the hands of a thoughtful boss like White Castle's Dave Rife, this can make for dramatic, emotionally charged TV. In the hands of a less-engaged exec, like Carstanjen, it starts to feel a little rote.

When Carstanjen presents his big reveal to his gimlet-eyed, well-dressed execs, the upshot of his argument is that Churchill Downs needs to "get a little bit personal" with its employees. But he doesn't seem to sway his fellow suits -- and it's unclear if Carstanjen himself is swayed.

Staying true to the show's formula, he gives nice, mildly lucrative surprises to all of his former supervisors, but there's little question that Churchill Downs will continue to squeeze every penny possible out of its workers, many of whom will have to struggle to put food on the table. If the purpose of Undercover Boss is to show the transformative power of working with the great unwashed, the Bill Carstanjen episode was a sad failure.