Steve Helling, Jill Smolowe, and Kristen Mascia
March 12, 2012 12:00 PM


A Time to Give


Orange County, Calif.

The news spread quickly across Los Angeles in May 2010. Someone had won the California lottery’s $266 million jackpot. When the report reached KNBC at 2:30 a.m., Jacki Cisneros, working the overnight shift as a TV assignment editor, fastened on a single detail: The winning ticket had been purchased at the local Hawaiian barbecue where her husband, Gilbert, had bought dinner just a few hours earlier. Phoning home, she woke Gilbert, who dug out the ticket and had her read the winning numbers. “He said, ‘I think we won,'” Jacki recalls. “I started crying. I was so relieved. No worries about bills or house payments ever again!”

While Jacki finished her shift, Gilbert, who had recently left his job as an operations resource manager at Frito-Lay, set up appointments with a lawyer and an estate planner. “I knew there were steps that we needed to do before we got the money,” he recalls. “We had things in order a week later.” Soon after, the indulging began. Gilbert special-ordered his dream car, a black 2011 Corvette. Jacki’s splurge? “I went to fat camp,” she says with a laugh. “I exercised all day and ate 1,200 calories. In three weeks I lost 20 lbs.”

Soon the couple hit the road to sightsee in Ibiza, lounge poolside in Maui and watch the Kentucky Derby from Millionaire’s Row. But after they settled into a 6,000-sq.-ft. Mediterranean-style house in Orange County with ocean views and a pool, Jacki began to miss working. “At 41, I’m retired,” she says. “Who does that?” Today she and Gilbert have found a new focus in charity work. Each gave $1 million to their college alma maters, and their Gilbert and Jacki Cisneros Foundation funds Hispanic education programs. “I’m busier than I have ever been,” says Gilbert. “Winning was a gift we were given to do something good.”


She Still Works as a Doctor


Until Shirley Press hit a 2001 jackpot, the only thing any family member had ever won was a case of baked beans. “Our lawyer called to tell us we were the sole lottery winner,” says the doctor and mother of two. “That was 7 p.m., Sept. 10. Then 9/11 happened. I felt an enormous amount of guilt.” For days she told no one. Then she tried the news on her mother, a Holocaust survivor. “Coming here with nothing, she always hoped she would win,” Press says. “She was so unbelievably happy.” Now Press is enjoying the pleasures of her bounty. Since scaling back her hours in a pediatric ER to a part-time post, she has created a movie club, joined Hadassah and been named to the boards of two charities. As for her windfall, she’s started a foundation to help provide medical care for Holocaust survivors.


He Owns a NASCAR Team


Fredericksburg, Va.

An unemployed construction worker hit hard by the recession, Joe Denette was barely scraping by on occasional handyman jobs when he bought 23 lottery tickets in 2009. It proved a lucky splurge. One of three winners to split a $225 million jackpot, Denette says, “The first thing I said was, ‘I’m going to buy me a truck.’ Then I thought, ‘I can buy anything I want. I could have an entire NASCAR truck-racing team.'” A huge NASCAR fan, he plunked down $600,000 and became owner of Denette Motorsports. Today Denette, now married and the father of an 11-month-old son, travels NASCAR’s Camping World Truck Series circuit with his team, changing tires, holding signs and chatting with drivers. “I can go to as many NASCAR races as I want,” he says. “Almost every day, I wake up and wonder if I’m dreaming.”


Twenty Years Later

KIM HAGGARTY, 43 | Steamboat Springs, Colo.

After winning millions in the Colorado lottery in March 1992, Kim Haggarty immediately began to hear from old friends and relatives. “A lot of people asked for a lot of money,” she says. “They think that because you didn’t earn it, you should just give it to them. I had to learn to say no.” Haggarty, whose annual after-tax payments of $530,000 will end in 2017, was determined to make smart choices with her wealth. “I knew if I was stupid with the money, it would be gone,” she says. “So I started investing.” After splurging on a $1.3 million, 5,700-sq.-ft. mansion in Steamboat Springs, she got down to business. Partnering with her brother, Haggarty, who appeared on TLC’s The Lottery Changed My Life, opened the Sweetwater Grill, an upscale riverside restaurant with views of the Colorado Rockies. Last year she purchased a music store in downtown Steamboat Springs, the perfect place for her children (Hanna, 15, Kayla, 12, and Trey, 7) to do odd jobs to earn their allowances. “My kids have to work for their money,” Haggarty, who teaches ice-skating lessons on the side, says, laughing. “I want them to learn the value of a dollar.”

The Jackpot Jinx:


William “Bud” Post’s $16.2 million windfall bought him nothing but heartbreak: He died broke at 66. But his story isn’t unique. From careless spending to plain old bad luck, “the lottery can ruin lives,” says Dr. Steve Danish, a psychologist who’s counseled winners. For some, curbing the temptation to spend is a challenge; anxiety over managing money adds to the burden. Says Danish: “It’s easier to imagine winning than living it.”


With a Strong Belief, She Beat the Odds

CYNTHIA STAFFORD, 49 | Pacific Palisades, Calif.

Cynthia Stafford puts great stock in the power of positive thinking. “Everything starts with your thoughts,” she says. “Whatever it is you want to achieve, you’ve got to believe in it first.” One thing Stafford believed in fervently was providing a loving home for the five children of her brother Keith, who was killed in a 1999 car accident. After rescuing the kids from foster care, Stafford quit her job as a computer-training account executive and settled in to be a full-time aunt. As the years ticked by, money grew tight. “The kids were asking for things,” she says. “I did not like telling them no.” The solution came in a vision. When the number $112 million appeared in her mind in late 2004, Stafford wrote it down, put it under her pillow and set her mind to winning the lottery. “I would meditate on it a few moments a day,” she recalls. “I would see myself winning.”

When a Quick Pick jackpot rose to her magic $112 million mark in the spring of 2007, Stafford bought a ticket. The winning number, announced on Mother’s Day, proved to be hers alone. “It definitely changed my way of living,” she says. She divided the haul with her dad and another brother. Childcare and expenses had been “a family effort,” she says. “It just felt right.” She also set money aside for her nieces’ and nephews’ futures, started a foundation that exposes underprivileged local kids to the arts and indulged a self-professed shopaholic streak (many Birkin purses, one Bentley convertible).

Then Stafford got back to the business of positive thinking. She envisioned a film production company, then founded it. She also envisioned her perfect guy. “I had a list of qualities I wanted,” she says. She found him-on the set of her first movie. Now married to Lanre Idewu, 35, who owns a fitness company, Stafford still plays the lottery. “Why not?” she says, laughing. “This time I’m visualizing a much larger amount.”

A Lottery Winner


When he won the $79 million state Powerball jackpot in August 2010, former West Virginia Magistrate Judge W. Randy Smith, 64, knew exactly what he’d do. “I worked in the public sector all my life,” he says. “You see the needs.” So after taking a $44 million lump sum, the divorced father of two set aside nearly $9 million to help his local sheriff’s and fire departments and established a fund to assist local nonprofits. Thanks to his donations, his native Berkeley County has new ambulances, fire trucks and a mobile forensics unit and will soon break ground on a rec center. “In 20 years in philanthropy, I’ve never seen anyone with his dedication,” says Amy Owen, executive director of the community organization running his fund. Ever humble, the town hero says it’s no big deal. “As my daddy used to say, ‘You never see a luggage rack on a hearse,'” says Smith. “This is a gift, and there’s a real need out there.”

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