Because of this combination of cachet and auction fever, the lots fetch sums that bear no resemblance to their market values: Last year a group of Tuscan wines available at retail for about $5,000 sold for $160,000. While the wines on the block are all the best of their type, Ackerman admits, “There is no relationship between what you pay to get it and what you receive. It’s like making a donation to a charity, and getting a door prize in exchange.”

Trustees say they are leveraging human nature—notably, the competitive instinct of wealthy, type A personalities such as themselves. “We’ve all got egos; that’s why we have been good at what we do,” Ackerman says. This competitive spirit animates even the planning stages of the auction, when event organizers push fellow trustees to cough up more and more in the way of auction lots. “It’s a riot; people just get caught up in the spirit and say, ‘Here, take my private jet to fly the winners down to the Kentucky Derby, take my air miles, take whatever you need,’” Denise Cobb says. Couples also compete to excel at their assigned tasks, from organizing transportation to ordering confetti. “There is a lot of peer pressure between the couples; you don’t want to drop the ball and have your spouse annoyed at you,” Brian Cobb adds.
 
Charitable Interpretation
If egos ever threaten to run amok, one simple phrase seems to restore focus: “Remember, it is all about the kids.” 

“That sobers us up and gets us back on track, because we have all seen how much of a difference this money makes to the organizations,” Clinton says. To literally drive home the point to donors that the frenzied bidding on Sunday will be going to worthy causes, attendees are escorted on bus trips to the charities that benefit from the auction’s proceeds. These trips display the stark contrast between the opulence of the trustees’ world and the lives of the children whose parents work for minimum wage in local restaurants and stores. “Naples is two communities, and the kids we serve, well, you’re not going to see them playing on the beach,” Brian Cobb says.

Naples is located in Collier County, which does not set aside local government funding for social services, neither homeless shelters nor day care centers. As wealthy people have flocked to this Gulf Coast community, the population of low-wage workers also has ballooned, driving up the need for community services. One of the beneficiaries of the auction provides those crucial services. Fun Time Early Childhood Academy has operated out of a double-wide trailer for more than four decades. Its condition is so poor that the facility can accommodate only 50 of the 93 children it may accept under its license, says Kim Long, its chief executive. With a countywide waiting list of 2,500 children queuing up for subsidized care, Fun Time had been trying for years to find a way to build a better nursery facility. “But capital funding is very difficult to obtain from the usual foundations,” Long says. Over the past two years, the auction has donated $1.2 million to Fun Time, enabling it to break ground last December on a new building that will triple its capacity. The Naples foundation also helped the academy lease land from the city for 99 years at a rate of $1 per year.

“The impact of this event has been immense,” Long says. There are unexpected benefits, as well. Last year, one wine auction attendee who toured the facility was so impressed by what he saw that two weeks later, a trustee arrived with a personal check for $35,000 to endow a library in Long’s honor. “We have been a United Way beneficiary for 35 years,” Long says, “but it has been these gifts that are transforming the organization completely.”