The Sweepstakes Winner

Meet Jay Sokolow, a man whose hobby is entering – and winning – radio and online contests and sweepstakes!

He leaves the radio on at work, holding a phone to each ear during breaks, speed-dialing stations during giveaways. He won so many times on one show that its producers instituted a once-a-month win limit: They call it the "Jay Sokolow law."

Other husbands might spend their free time golfing or gambling. To his wife’s aggravation, Sokolow enters contests. Grocery store drawings, sweepstakes, trivia games, raffles, he enters them every day, except on the Sabbath — Friday night through Saturday.

It is not so much the value of the prizes that entices him, but the probability of winning. There is a strange satisfaction, he says, in beating the odds, outsmarting the other players, and sometimes outsmarting the contest promoters.

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