'Undercover Boss' Plays Ball With the Chicago Cubs

When I heard that Undercover Boss was going to feature Todd Ricketts, one of the owners of the Chicago Cubs, I assumed the show would follow its familiar pattern of featuring unbelievably cheerful workers overcoming horrendous challenges while protecting the company from their bosses' attempts to do their jobs. Happily, there was more to the show this time around.

The most recent episode of the hit CBS (CBS) reality show was refreshingly light on the sap that has made the program almost unbearable to watch. Ricketts was also an an appealing star. He is the youngest member of the Ricketts family, who acquired the Cubs last year for $845 million, and his role on the team has yet to be defined. Ricketts needs to prove to his family that he can be trusted with a real job.

Ricketts presented a unique set of challenges. In every episode, colleagues of theundercover boss are told that they are helping the company determine whether to hire an unemployed person who is participating in a reality show. Ricketts was given the secret identity of out-of-work roofer named Mark Dawson. Ricketts, who was a huge Cubs fan before his family owned the team, was up for the challenge, saying he needed to know how things work and how to make them better. Unfortunately, he didn't look the part and didn't act like had done much manual labor in his life.

Another Line of Work

The undercover boss quickly struck out with his supervisor Darrell because he was too slow in cleaning the stadiums bathrooms. Ricketts insisted that he was moving as fast as he can. But Darryl, a 24-year veteran at Wrigley Field with a daughter who is an avid swimmer, commented (without knowing the irony of his statement): "The Ricketts family can't count on Mark to take the bathrooms to the next level." Then Darryl promptly fired Ricketts, saying, "I don't think this is right for you."

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Crestfallen, Ricketts tried to redeem himself as a hot dog vendor with the help of Rocco, a veteran whose family was in the business. Ricketts was probably the most awkward hot dog vendor in history. He managed to unload most of his dogs, except for the last four. Rickets paid for those with $20 from his pocket and then threw them in the garbage. Rocco figured this out and confronted Ricketts, understandably thinking that he was throwing away profits. Ricketts lied to Rocco, a ruse the vendor saw through immediately.

The shenanigans continued at his next assignment at the team's parking lot where an old college roommate exclaimed, "Are you really parking cars?" Ricketts had to reveal his true identity and plead with his friend not to blow his cover. His boss Jose, who had criticized Ricketts for parking the cars in a crooked line, was not happy that someone who supposedly needed a job "disappeared" for a while. Jose told Ricketts that the lot used to have an air-conditioned trailer but it was removed. He also mentioned that he was pursuing a career teaching English as a second language.

Ricketts also frustrated the grounds crew. He struggled to pull the tarp over the field and was reminded by co-worker Joe that "in the Major Leagues, every detail counts." While the two went to lunch, Joe told him that he had graduated from college and that his dream job was to work in the Cubs front office.

Undercover Redemption

At long last, Ricketts redeemed himself with Darryl, who also operates the manual scoreboard at the stadium. He turned over numbers just fine. Amazing how someone could have the worst job at Wrigley and the best.

In the end, Ricketts proved to be more humble than expected. He apologized to Rocco about the hot dogs and awarded him the first annual Wrigley Field Award for his contributions to the stadium, along with a $1,000. In addition, Rocco got to throw out the first pitch of the last game of the season. Ricketts offered to pay for the rest of Jose's schooling and agreed to provide him with a trailer. Darrell's daughter was given swimming lessons from the head swimming coach at Northwestern University. His family will also be Ricketts's guest at spring training in Arizona. Joe got an internship at the Cubs' marketing department.

Overall, this episode was a single in baseball terms. Better than a strikeout, but not enough action to score some points.