Enter the world of Sokolow He enters it all -- but not just to win

Times Staff Writer

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 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.

Sokolow’s obsession began as a teenager, when he spotted a jar of half-dollars on display in a bank window. He correctly guessed the 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.

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 the useless prizes that have accumulated in their house over the years: 14 T-shirts from Coors beer, a case of Oreos produced before the cookies went kosher, Furby toys, an autographed toy race car, World Wrestling Entertainment posters, a jazz CD for lovers, a toy spy set, Bratz dolls.

When she can’t stand it anymore, she gathers everything up in bags.

“We’ve outfitted the local shelter with T-shirts and hats,” she says.

But Sokolow has also won gifts that his wife and children didn’t mind: two tickets to any Frontier Airlines destination, along with $700 in American Express cards, tickets to the AFC Football 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 he 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 a ring that Johnny Depp wore in “Pirates of the Caribbean.” It was the lesser prize in a 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.

Ina, 49, talks in the kitchen on a Nokia cellphone, which Sokolow won. His daughter shows off a long-sleeve Yankees shirt she just received in the mail. He won that too. He has also won three iPods, two of which went to his 18-year-old son; the third 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 it 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 a poor man. Nor is he a bored man.

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.

The home they share with their teenagers is two stories and gray, with a yellow sprinkler on the lawn and a Toyota Prius parked in front. Two 3-foot-high cement planters sit near the front door, prizes that Sokolow won along with gardening tools after he filled out an online form for a gardening company that has since gone out of business.

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 -- with his eyes closed -- showing off his ability to name the colors of M&Ms; by taste. She didn’t believe him, so she fed each color to him.

“Sure enough,” she says, “he could identify them.”

They married in 1985. Ina 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.

It wasn’t until he got hooked on the Internet that his hobby became an obsession.

Before the Internet, most people could enter contests only through the mail, says Ken Carlos, co-owner of Sweepstakes Advantage, one of Sokolow’s favorite contest websites. The Internet has linked thousands of contest lovers, Carlos says, and it allows them to exchange tips, talk about prizes, enter more easily and win more often.

Sokolow bookmarks contest websites and follows his own hierarchy of important links: big prizes, easy wins, and contests that allow him to enter once a day. Contests he has never had luck winning, like those offered by Redbook magazine, end up at the bottom of his list.

He triples his chances by entering himself, his wife and his 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. Clicking on an entry form often forces him to watch a 20-second online video ad.

Some contests require knowledge about pop culture, history, entertainment or politics, all of which Sokolow is well-versed in. No one in his family wants to compete against him in a game of Trivial Pursuit.

Aside from online contests, Sokolow regularly competes in radio and television giveaways, even when the prize isn’t announced in advance. He uses a calendar to track his eligibility to enter the contests sponsored by the radio station that named the once-a-month rule after him. He often uses the Internet to find answers to the station’s trivia questions.

On a recent “Chaz and AJ in the Morning” show on New Haven’s WPLR-FM, the James Bond theme song plays and the host announces: “Impossible Trivia.” The question: “According to a recent survey, in the workplace 1 out of 4 workers say this ticks them off about their co-workers. What is it?”

Sokolow is the first caller to get through. He quickly finds the answer online because he has figured out that the radio show’s daily trivia questions come from a particular website.

“Workers who hug them,” Sokolow answers.

“Aw, c’mon,” the announcer replies.

Sokolow lets out his signature monotone: “Yaaaaay.”

“Oh, it’s you!” the host says. “Has it been 30 days already?”

With 100,000 listeners across the state, Chaz says he doesn’t know how Sokolow beats out all the others. “He loves being the guy who can answer the question,” Chaz says. “He loves being the smartest kid in the class.”

It is relaxing, Sokolow says, to enter contests on his computer after a long day at work, while watching “The Simpsons” on television.

Sitting on his backyard deck furnished with green-cushioned patio furniture (which he won), Sokolow clicks his “favorites” tab on his white Mac laptop. He skims through the latest contests: a trip to Big Sur, a Prius, $10,000 in cash.

Sokolow notices a computer giveaway contest.

“I haven’t done this Dell one,” he says. “I’ll have to catch that later on.”

He won a Dell computer once before, but he’s a Mac guy, so he donated it to a school. “I still want to win a car,” he says. “That’s the big prize that I haven’t hit yet.”

Enjoying a root beer float in the kitchen, Ina 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 chocolate-colored 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.

Ina rolls her eyes. She doesn’t make guacamole.

Sokolow says he’s been trying for an iPod Nano, a prize offered in an ongoing contest from a guacamole company, but so far he has won just the bowl.

“Everybody likes to win stuff,” Ina says. “They don’t realize you have to pay taxes on it, and sometimes you pay taxes more than the item is worth.”

Sokolow pretends not to hear.

“Entering a contest is a very optimistic thing,” he says. “You don’t enter thinking of ‘I’m never going to win.’ So I always enter, and I think ‘Gee, maybe it will be nice to get a guacamole bowl or whatever.’ ”

Ina rolls her eyes again.

He looks at her. “Eventually we’ll use this.”

“Have you seen the closet in the basement?” she says.

Twenty-two years of marriage, she says, living like this.

“Most felony sentences are much shorter than that,” Sokolow says.

They both laugh.

“We’ve both changed a lot since we’ve been married,” he goes on. “I mean, I don’t think I’ll do contests for the rest of my life.”

“Yeah,” Ina says, “you probably will.”

“It gets to the point where it’s fun winning stuff but it’s not so much of a challenge when you know that you can,” Sokolow says.

“Just innocent fun,” Ina says, stretching her legs, resting her feet in his lap. Sokolow puts one hand on his wife’s foot.

The couple’s black poodle crawls onto Ina’s lap, and she pets the dog. Its name is Mazel. In Yiddish that means “luck.”