'Undercover Boss' Todd Ricketts Plays Ball with the Chicago Cubs

undercover boss todd ricketts chicago cubsWhen Todd Ricketts goes undercover at Wrigley Field, he has the daunting task of messing with an American institution. He is the youngest of four siblings who acquired controlling ownership of the Chicago Cubs just one short year ago. While he believes fans are happy that at last their beloved team is family owned rather than corporate owned, he understands that tradition reigns supreme, and any changes will be scrutinized and discussed -- at length.

"We're not the kind of owners who, like a corporation, are going to come in and throw a lot of money around and buy five top players to win the World Series next year," he said. He explained that the family plan is to strengthen the farm system and have more sustained, steady growth that will keep the team strong for many years to come, and not be entirely dependent on a couple of flashy superstars.

They're not the type of owners who seek media attention and make grand, showy gestures either. They learned this lesson well from their mother. On the day their father took Ameritrade, the business he started from scratch, public, Ricketts called his mother and said, "Hey Mom -- what are you doing right now that you've become a millionaire?" She replied: "Oh Todd, I'm cleaning the bathroom!"

The bathroom blues

undercover boss todd rickettsRicketts got to see what it was like to use industrial strength cleaning methods on the bathrooms at Wrigley Field as part of his 'Undercover Boss' experience. "It's pretty dramatic," he said. "They use fire hoses and power wash, and they move very quickly. It's a lot of physical work." And, according to Darrel, who supervised his efforts, Ricketts wasn't up to it. He may be the first Undercover Boss who was actually fired from his position, he did it so poorly.

He tried to make it up to Darrel later -- it seems Darrell also runs one of the only two remaining manual scoreboards in the major leagues. Ricketts did a much better job putting the right numbers in the right slots, so, when the two men met later and Ricketts' identity was revealed, it wasn't as awkward as it could have been. The two men have eight-year-old daughters who swim competitively, and Ricketts arranged for Darrell's daughter to be coached by the championship swim coach at nearby Northwestern. He also arranged for Darrel and his family to take an Arizona vacation while the Cubs are in Spring training.

Ricketts was more excited about his prospects working with the grounds crew. "I actually prefer to be outside, to break a sweat," he said. "I'd rather work outside than in an office." Physical work is nothing new to Ricketts, who worked pouring cement in high school and did various other backbreaking jobs.

Now he can add preparing a field for a game to that list. It had rained that day, so the crew had to remove a very heavy tarp from the field, then quickly sprinkle special sand on the baselines like chicken feed. He also raked, fertilized and watered. Joe, the grounds crew staffer Ricketts worked with had just graduated from college with a business degree, and was looking to shift his career after five years at Wrigley Field. He dreamed of working in the Cubs' front office.

So it came to no surprise to viewers when Ricketts, sans disguise, offered Joe a paid internship, off season, in the marketing department.

Not so great parking karma

Rickets also got to work outside in the parking lot. The lot attendants used to have a somewhat comfortable, temperature-controlled trailer, but Ricketts saw that all they have now for shelter is a 4x4 shed. He also found out that parking the cars correctly is tougher than it looks, and his lack of skill caused some cars to be boxed in. Jose, the attendant he worked with, thought he could be a little more exacting and assertive.

Jose revealed that he was working to earn enough money to finish his education as an ESL teacher, but it was tough. Naturally, when Ricketts met with Jose as the owner of the Cubs, he offered to pay to complete his education -- and replace the comfy parking trailer.

Shy by nature, Ricketts says he was chosen among his siblings not only because he was less recognizable than his older brother, but because his sister was pregnant and his other brother lives in Nebraska. "You could say I was taking one for the team," he said. "But I guess there was a willingness factor."

No wiener wonders

Being willing can't make up for being shy when selling hot dogs, however. When Ricketts tried to help Rocco, the vendor who was training him, he found he was hurting sales more than helping them, so he clandestinely slipped a little cash in the tin and tossed the remaining four hot dogs into the trash. When Rocco caught him, he actually lied about it. Rocco wasn't fooled, and Ricketts felt terrible. Rocco was unaware that Ricketts had paid for the hot dogs.

AOL Jobs Asks
Undercover Boss Todd Ricketts
5 Quick Questions

1. What was your first job? A paper route.

2. What inspires you? I'm driven by the idea of leaving our country better than it was when we got here. I want to improve it for our kids.

3. What is the most important trait needed to succeed? You need to continue on after you fail.

4. What is your biggest challenge? Leaving a legacy --something valuable for the next generation.

5. What is the best career advice you ever received? Do whatever it takes. Once when I had a new job and I wasn't quite sure what to do there, and my dad told me, "If they let you empty the wastebaskets, consider yourself lucky."

Many hot dog vendors take their jobs very seriously. They buy the dogs they sell, and many of them have been working with the same fans in the same box seats for decades, and they've established a rapport. Some even make a living selling concessions in the stands all year round, at various stadiums during various seasons in this sports-loving town.

Rocco had been on the job for 28 years, and was very pleased when Ricketts not only confessed, but made him the recipient of the first annual Wrigley Field Award, which included $1,000, box seats, and the opportunity to throw out the first pitch at the last game of the season.

In addition to the individual perks Ricketts handed out, he and his family also pledged to clean out and update the crew locker room, have a family appreciation day for the staff, get walkie talkies for the cleaning crew so they wouldn't have to communicate via their personal cell phones and put up a suggestion box so the staff can have more input.

In Chicago, baseball is so much more than just a game. All you need to do is ask the fans, stadium workers, team members and owners, as Ricketts did during his stint as an Undercover Boss. Previously, he'd learned to work with his family as professionals. Now he knows how to work with the professionals as family.

Want more 'Undercover Boss'?

-- Interviews with Season 2 Bosses [AOL Jobs]

-- Boss's True Identity Exposed? [TV Squad]

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Barbara Gilman

11-09-2010 @4:58PM
Barbara Gilman said...
vote upvote downReport Neutral

And he lied? He lied! A bold, bare-faced lie. He said he did not throw the hot dogs away. An incredible example of our loose society. Lying is all right "until you get caught", I've heard kids say but Todd never buckled even faced down.
Hope none of his employees are penalized for lying.

November 09 2010 at 7:34 PM Report abuse rate up rate down Reply
Barbara Gilman

And he lied? He lied. A bold, bare-faced lie. He did not through the hot dogs away. An incredible example of our loose society. Lying is all right "until you get caught" I've heard kids say but Todd never buckled even then.
Hope none of the employees are penalized for lying.

November 09 2010 at 4:40 PM Report abuse rate up rate down Reply

As a "cursed by birth Cub fan", I watched the program. I thought Rickett's came off like a jerk.

November 09 2010 at 10:05 AM Report abuse rate up rate down Reply

They Gave The Cleaning Crew walkie talkies so they would nt have to use Their OWN PHONES ! ! WOW ! Lets see, > Walkie Talkies For 15 People Maybe 20? THATS CRAZY GENOROUS ! Then He Bought 4 Hotdogs $$$ Oh & the $1000 Box Seats That havent been Filled ! WOW ! UNREAL !

Now to The "4x4 SHED", How nice that they now have a trailer... DID YOU GET one of those Nice US Government Trailers That they Made for Katrina? The 4ft x 4 ft Shed Was More Than enough for 5? ! guys.
And That Pledge To Clean out the Locker Room Was OVER THE TOP ! Wow WHAT A PLACE TO WORK !

November 09 2010 at 2:40 AM Report abuse rate up rate down Reply

Oh it is so wonderful how the compassionate bosses come down from Olympus and grace the lowley peons and wage slaves with their wonderful presence and perform wonderful acts of kindness for the people who labor for them and make them rich. This show makes me want to puke!

November 08 2010 at 11:52 PM Report abuse rate up rate down Reply


November 08 2010 at 11:37 PM Report abuse rate up rate down Reply

Every episode is the same. The boss works with "random" employees, all of whom have heartstring pulling kinds of stories. It's the same every episode, and obviously contrived.

November 08 2010 at 11:19 PM Report abuse rate up rate down Reply

Glad to see they did a show at Wrigley! The Cubs and their fans are the greatest. I take my Dad to a game at least once a year, and we have a great time, the ball park is awesome. I got the DVR set every week for this show and havent seen this episode yet, but will be watching it soon. GO CUBS!!

November 08 2010 at 10:50 PM Report abuse rate up rate down Reply

Cubs fans live and die for their team. Employees who have worked for the organization should receive incentives based on five year increments. Instead of receiving a severence package at the end of their carears they should receive bonuses for 5, 10, 15, 20, 25 and 30 years. Organizations know that some fans would work for free and so they take advantage of that. Free doesn't feed the Bull Dog. Pride of Ownership shown by the employees is priceless and brings big bucks to the organization. A million dollars spread out amongst the working class would not cripple the organization. Their are players that don't start and make more than a million dollars in one season. Think about it.

November 08 2010 at 10:32 PM Report abuse rate up rate down Reply

Boy, I sure wish I lived in 1950's America the way half of you posters do. Are you serious? This fantasy world you live in where every corporation is out there to help the little guy? Please, I'll be taking my large economy sized break now. Then you have the audacity to come and post negative comments about people being cynical. How about you wake up and open a newspaper or watch the evening news. Better yet, how about watching something unbiased like the Daily Show with John Stewart. Then come back and tell me how kind hearted and generous corporate America is. GROW UP!

November 08 2010 at 10:27 PM Report abuse rate up rate down Reply

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