An October 2004 article in the online magazine Slate told of a strange subculture of people known as "sweepers," who dedicate their lives to entering sweepstakes. These people spend sometimes more than 40 hours a week and thousands of dollars a year to send postcards, self-addressed, stamped envelopes and entry blanks to companies running promotional sweepstakes, in the hopes of winning cars, trips, money or just small prizes. Curious to discover the no-doubt disturbingly obsessed practitioners of this bizarre art, I check out the listings on the website of sweeper fan magazine Sweepsheet and head to a local meeting of sweepstakes enthusiasts.
Alas, the closest I find to a true obsessive is retiree Joanna, who, along with her boyfriend, Jim ("We don't live together," she assures me), spends three or four hours a day entering sweepstakes, mostly online, which the entire group informs me is the way to go these days. Joanna and Jim also, like many local retirees, spend much of their time gambling, and are adept enough at earning comps that they tell me they haven't had to make themselves meals in two years.
The rest of the small band—six people, including one daughter who's just along for the ride—are hobbyists at most, no different from any other group of enthusiasts getting together to discuss their particular proclivity. The group, led by 42-year-old Linda, who works in travel marketing, has been meeting for two years. None has won a car or a mountain of cash, but they've gotten plenty of second and third prizes—T-shirts, show tickets, the occasional short trip. Linda's sister-in-law, who inspired her to start entering sweepstakes, has won two cars, a number of trips and $10,000—and a prize in a Review-Journal sweepstakes when she was visiting Las Vegas.
It seems odd to ascribe to luck what appeared at first to be so businesslike, but the members of the group deride those who treat it as such, who enlist their children to fill out forms. "The best things are the relationships," says Linda, whose close friend, 32-year-old homemaker Karin, sits across from her. Karin's area of expertise is radio call-in contests, and Linda always listens for her friend to win concert tickets. The two often share prizes.
At the meeting, there are a few drawings for vital sweepstaking paraphernalia, like eye-catching envelopes and sheets of stamps. I get the honor of drawing two of the winners. Karin breaks out a giant cookie for the group to share; it is, of course, a prize from a sweepstakes she's won. On the cookie is written "Good Luck," an appropriate sentiment for this group of disappointingly normal people who are all winners, but not obsessed with being so.