Ep 7. Chicago Cubs

Undercover Boss is an American reality television series that follows high-level corporate executives as they slip anonymously into the rank-and-file of their own firms. Season 2, Episode 7 takes us into the world of Chicago Cubs, one of the most iconic baseball teams in MLB history. The Cubs are a storied franchise, replete with legends such as Ernie Banks, Ryne Sandberg, and Sammy Sosa, among others. But what’s it like working behind the scenes for this beloved institution? That’s the question that drives this episode, which features the team’s Chairman, Tom Ricketts, on a journey of discovery as he assumes several different roles throughout the organization.

As with all episodes of Undercover Boss, the premise is simple: the boss goes “undercover” and works alongside his employees, getting an up-close-and-personal look at what it takes to keep the company running. But while the formula is familiar, there are always surprises. In this episode, we see Ricketts donning various disguises, including a bearded janitor, a security guard, and a cook. Ricketts is a great sport, gamely participating in whatever tasks are assigned to him, whether it’s scrubbing toilets or serving food at the Wrigley Field hotdog stand.

The appeal of Undercover Boss lies in the way it humanizes the executives at the top of these companies. In this episode, we see Ricketts grappling with the same issues as his employees—low pay, long hours, and the daily grind of trying to satisfy customers. But we also see the ways in which Ricketts’ position gives him a unique perspective on the company. He observes first-hand the ways in which different departments interact (or don’t), and he gets a sense of the overall culture of the organization. It’s a rare opportunity to see a boss learn from his employees, and there are some real moments of insight and humility throughout the episode.

One of the most interesting elements of this episode is the way it explores the unique challenges faced by the Cubs as an organization. Baseball is a notoriously difficult business, with long seasons, demanding fans, and unpredictable players. The Cubs, in particular, have had a history of struggle and heartbreak, having gone over a century without winning a World Series. We see how this legacy affects everyone from the ticket takers to the mascots, who are all acutely aware of the pressure to deliver on the field. It’s a stark reminder that even something as seemingly trivial as a baseball game can have immense significance to those who are invested in it.

Another theme that emerges in this episode is the importance of teamwork. Ricketts observes that the different departments within the Cubs organization often operate in silos, with little cross-collaboration or communication. He sees how this can lead to misunderstandings and inefficiencies, and he makes it a priority to foster more collaboration and cooperation. It’s a valuable lesson for any business, and one that Ricketts clearly takes to heart.

Ultimately, the biggest takeaway from this episode is the sense of pride and dedication that characterizes the Cubs organization. Ricketts is deeply moved by the passion and enthusiasm of his employees, who work tirelessly to make the team successful. He comes away from his experience with a renewed appreciation for their hard work, and a deeper understanding of what it means to be a part of the Cubs family. Whether you’re a die-hard Cubs fan or just a casual observer, this episode is sure to leave you feeling inspired and entertained.