12/22/2008 05:12 am ET | Updated May 25, 2011

A Peek at Chicago's 'Hidden Rich' (Warning: Mature Content Matter)

They used to lament "the hidden poor" in this country.

I think the bigger blind spot these days is "the hidden rich." I think we're easily shocked by their numbers and by the scope of their excesses--especially in Chicago, with its lunch-bucket self-image. Even if you're reasonably well off, Chicago neighborhood life yields more contact with the very poor than the very rich.

But sometimes you get unlucky, as I did the other day, when my wife wrote me, "Check out the email from Montessori today. Holy shit."

We pay about $15,000 to send my five-year-old daughter to a private Montessori school, because my wife, who teaches in a public charter school, knows all too intimately that public schools don't deliver a modicum of the tender love our little baby gets at home, let alone the thoughtful Montessori education we want for our only child.

So we bite the bullet. But the bullet isn't all.

Every year the school holds what it preciously calls a "Galaesque," to raise funds in addition to the massive tuition. This year my wife coordinated a project that produced a kid-made quilt for the live auction. Last year, we gave money to pay for a teacher to be able to attend.

But we wouldn't think of going ourselves. (The less we see these people, the less likely we are to feel hatred or envy, either of which might upset our fragile socioeconomic equilibrium.) When confronted by the school's founder and forceful "directress," my wife says, "We're not black-tie people." So far, the line has proven unanswerable.

So I'd ignored the all-parent e-mail previewing the items for the live auction.

But: Holy shit, indeed.

Among the "packages" listed:

International Humanitarian Experience
Travel to South Africa to work as a family on a humanitarian project! Tickets to Johannesburg Zoo and Golf Reef City, and guided tour of Nelson Mandela Square and African Craft Museum. You will have an exquiste [sic] 1150 SF hotel suite at the Park Hyatt with Butler Service and in-room babysitting!

Instant Wine Cellar
102 bottles of wine from families at the Academy, each with its own special story of how the bottle made it to the lot. One year of wine storage at East Bank Storage, and an in-home party hosted by Sommelier Perry Fotopoulos (founder of the Randolph Wine Cellar).

Ultimate Bears Fanatic
Two Tickets to December 22, 2008 Bears vs. Packers night game at Soldier Field; sit in the broadcasting booth for one full quarter with Marv Albert. Seven hours limo service from VIP Valet Services, plus dinner at Mortons' Chicago.

Stay for 1 Week with [the directress]'s Mom
Relax Caribbean style on the beautiful island of St. Croix with [the directress]'s own mom. Enjoy the finest of warm Italian hospitality, as [the directress]'s mom hosts you and your family for one week in their award winning coastal home. Also included, breakfast each day, a special sail to Buck Island on [the directress]'s mom's boat, and SCUBA lessons for two from Dive Experience.

The Best Dinner Party Ever
Imagine hosting a dinner party at your home with 10 of your closest friends, and you don't have to lift a finger. Dinner will be cooked in your home by Mark Mendez--head chef of Carnivale and entertainment will be provided by Acoustic Guitarist Jennifer Trowbridge. Treat your guests in style, and enjoy memories of the whole evening with professional photography from the [the school]'s own Kia Hinz.

Year of Me
All of life's little accommodations [sic] taken care of for an ENTIRE YEAR, such as: Wine delivered to your home once a week, a personal chef to come to your home once per month to cook for you and your family, a special birthday party for up to 25 friends to be hosted at the Kavi Gupta Gallery, champagne and cocktails included, personal shopper to help you through important events and meetings, and 52 weeks of 15 hours per week of a personal assistant to schedule meetings, events and run errands for you!! If that's not enough, you'll also get one year of spa and salon services provided by Beauty Mark Salon and Urban Spa Chic, a year of massages, a one year membership to CRUNCH fitness, etc ... all of this, plus your very own parking space at [the school]!!

Chicago Celebration
Hate the idea of going away to have a vacation? This package allows you and a special friend to have it all while staying in your own home town! Enjoy the best that Chicago has to offer--hotel stay at the Drake, dinners at Powerhouse and N9NE, 3 hour chauffeured ride in 1964 Rolls Royce Silver Cloud, horse and carriage ride from Noble Horse, 4 tickets to the FINAL performance of WICKED, and lunch for 4 beforehand at SEPIA.

Prince/Princess Package
Turn your child(ren) into a superstar for a day. Have a special A&E styled documentary made about your child courtesy of Moxie Post. Once the film is complete, invite your closest friends to join you for the red carpet premier in the Theater Building Chicago! Dress your child in style thanks to Bullfrogs and Butterflies. This package also includes a special "Academy Styled" birthday party to be hosted by [three school staffers] as well as a special photography session with Audrey Woulard!

What would they offer if we weren't in a recession?

If you're like my wife and me, you're trying to catch your breath right now. But wait: There's one item I didn't share.

"One Year of Academy Teacher & Staff Babysitting. Once a week for the full year of December 2008-November 2009. Exact dates and times to be coordinated between parents and staff members."

That's right. It's not enough that the school's teachers and staffers give their work lives to your children's education for a salary that wouldn't pay for a luxury humanitarian experience. No, the Cinderellas also have to babysit the kids while you live out your ultimate Bears fantasy.

Holy shit!

I just hope--no, never mind, it's impossible. It would just be too absurd. But I can't help but worry--no, I shouldn't! But I do! Is it possible ... that any of these parents who attended the Galaesque and bid on the "Year of Me" are the same people who, in boring conversations at "The Best Dinner Party Ever," cite studies that prove it doesn't work to "throw money at the schools"?

No. No chance. Yes, the rich are different--and, thankfully, they are also largely hidden--but they're not quite the monsters I conjure when I imagine a family working on a luxury humanitarian project in Africa with butler service and in-room babysitting.

Are they?