Connecticut man the king of contests

NEW HAVEN, Conn. — Jay Sokolow can fill out 100 online contest-entry forms in an hour with the click of his auto-saved name and e-mail address.

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 drawings, sweepstakes, trivia games, raffles, he enters them every day, except the Jewish 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.

Sokolow's obsession began as a teenager, when he saw a jar of half-dollars on display in a bank window. He guessed the correct amount of money in the jar and won a 10-speed bike. He estimates that since then, he has entered more than 50,000 contests.

Wife: "It annoys me"

Sokolow's wife, Ina, halfheartedly accepts his contest-entering quirks.

"It annoys me in the evenings," she says. "I try to have a conversation and instead he's sitting on the computer."

She has put up with many of the prizes that have accumulated in their house over the years: 14 T-shirts from Coors beer, a case of Oreo cookies, Furby toys, an autographed toy race car, World Wrestling Entertainment posters, a jazz CD for lovers, a toy spy set, Bratz dolls.

But Sokolow also has won gifts his wife and children didn't mind: two tickets to any Frontier Airlines destination, along with $700 in American Express cards, tickets to the American Football Conference Championships, a trip to a resort in Mexico, a family cruise to Jamaica and two tickets to the Super Bowl.

He won a white-water rafting trip but negotiated $5,000 for it instead.

"Can you see him on a white-water raft?" asks his wife, glancing at her 5-foot-9, 220-pound husband, barefoot in an extra-large purple button-down shirt, with grayish hair peeking from beneath his yarmulke.

Sokolow, 49, won a trip to a golf tournament in Scotland but forfeited because he couldn't get away from work. He won a trip to the World Series of Poker in Las Vegas and a lesson from professional poker player Annie Duke, but the Sokolows don't play poker, so they didn't go on that one, either.

Recently, he received a replica of the ring Johnny Depp wore in the "Pirates of the Caribbean" movie series. It was the lesser prize in the contest for a Disney vacation or a pinball machine, but good enough. He gave the ring to his 16-year-old daughter.

The list goes on and on.

Prizes galore

Ina, 49, talks in the kitchen on a Nokia cellphone, which Sokolow won. His daughter shows off a long-sleeve New York Yankees shirt she just received in the mail. He won that, too. He also has won three iPods, two of which went to his 18-year-old son; the other he gave away as a bar mitzvah gift.

The red rotary phone near the couch, "The Incredibles" DVD in a stack near the wall, the CD player on the windowsill, the apple-shaped candy bowl in the living room: He won them all.

"Most people come home and look at the mail, and they figure it's just bills," he says. "It's depressing. When I come home, I'm always eager to look at the mail because there might be something fun in there."

Sokolow is not poor. Nor is he bored.

He is a radiologist in private practice and is president of his synagogue. He lives on a cul-de-sac in a leafy neighborhood in a town of 124,000, served by 30 City Council members, one of whom is his wife.

Sokolow grew up in the Bronx about a mile from Yankee Stadium and became a fan. But in high school, he spurned team sports. He joined the math team and his synagogue's youth group.

He majored in chemistry at Yale University, where he met Ina, an anthropology major. She remembers the day clearly. Both were eating in the Kosher Kitchen on campus. Sokolow sat at a table, showing off his ability to identify the color of M&Ms by taste, with his eyes closed. She didn't believe him, so she fed each color to him.

"Sure enough, he could identify them," she says.

They married in 1985. His wife hardly noticed when Sokolow signed up for a few contest newsletters. He entered a raffle while she was shopping for shoes at a department store and won $500. But it wasn't until he got hooked on the Internet that his hobby became an obsession.

High-tech approach

Sokolow bookmarks contest Web sites on his computer and follows his own hierarchy of important links.

He triples his chances by entering himself, his wife and son. His daughter is too young to qualify for most contests. For a shot at a prize, Sokolow usually must provide personal information, such as his e-mail address, birthday, phone number or home address. Each contest usually brings pounds of junk mail and torrents of spam.

Some contests require knowledge about pop culture, history, entertainment or politics, all of which Sokolow is well-versed in.

It is relaxing, Sokolow says, to enter contests on his computer after a long day at work.

"I still want to win a car," he says. "That's the big prize that I haven't hit yet."

His wife says the best prize he won was the cruise. "It's the only time we go on vacation, when he wins a trip."

"No, it's not," says Sokolow, entering the room holding a bowl that reads "Guac Squad" on one side and "DIP ME" on the other.

"I won this too," he says. "It's a guacamole bowl." He puts it on the table and sits down next to her.

His wife rolls her eyes. She doesn't make guacamole.