Chicago Cubs Exec Throws a Curve on 'Undercover Boss'


One of the unspoken themes of CBS's (CBS) Undercover Boss is that, under the surface, there really isn't that much difference between the executives who hang out in the head office and the drones who populate the shop floor. Every week, the people on the top and bottom of a company bond over children and food, parenting and ambition, inevitably discovering that -- once you strip away the seven-figure salaries -- they are pretty much the same. This Sunday, however, promises an interesting confrontation as an American aristocrat meets the workers who keep his family business -- the Chicago Cubs -- afloat.

Todd Ricketts, this week's guest on the show, is one of the four children of J. Joseph Ricketts, founder and former CEO of Ameritrade, which rose to become the top online discount brokerage in the world. In the process, it also made the senior Ricketts a billionaire: In 2009, he was number 371 on Forbes' list of the 400 richest Americans.

Rather than sit on his holdings, J. Joseph bought the Chicago Cubs in 2009, and installed his children in the front office. Today, the Ricketts kids occupy four of the six seats on the Cubs' board of directors, and son Tom Ricketts is the organization's chairman. It isn't really clear what Todd does for the Cubs: Co-owner of a pair of Chicago-area bicycle shops, he told reporters early this year that the Ricketts planned to spend a lot of time at Wrigley Field, but weren't going to seek media attention. Since then, he has largely kept his word, briefly surfacing in September 2010 when he co-sponsored a bicycle race to benefit Chicago Cubs charities, but otherwise staying out of the spotlight.

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All that is about to change, as millions of Americans will watch Todd clean toilets, sell hot dogs, maintain the field, man the scoreboard, and park cars. Asked about why he is doing this instead of his more prominent brother Tom, Todd claimed that his brother "can't grow a beard," and was thus unable to disguise himself.

Like many of the show's previous workers, Ricketts posed as a down-on-his-luck manual laborer, "Mark Dawson," an unemployed roofer whose name just happens to be a mashup of two former Cubs players. But, while undercover bosses disguise themselves with glasses or beards, it's harder to hide their attitudes. In every episode, the actual workers on the show appear desperate to hold on to their jobs and scurry to impress their higher-ups. Meanwhile, many of the bosses -- especially season one's William C. Carstanjen -- have shown disdain for the menial tasks that they were asked to perform. In Ricketts' case, this proved especially problematic, as he was fired from the bathroom crew and lied to Rocco, the hot dog guy who was tasked with mentoring him.

Undercover Boss being what it is, the show will inevitably have a happy ending: The workers will discover that "Mark" is actually their incredibly wealthy boss and Ricketts will use his new-found knowledge of the Cubs' employees as an opportunity to play Santa Claus. Hard workers will be advanced or receive gifts, while less-inspired employees will learn that the boss man has his eye on them. More to the point, however, the audience will have their eye on Todd Ricketts in hopes of seeing a hint of awareness at the incredible genetic lottery that he won and the lifestyles of those who are less lucky.

Undercover Boss will air on Sunday at 9 p.m. on CBS.

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Also See: Undercover Boss Todd Ricketts: 5 Quick Questions