Life After Lottery: Winners Discuss How Life Changed After Hitting Jackpots; Keeping It Secret

The only thing better than winning the lottery is doing it anonymously. There are countless stories of lottery winners who've gone bankrupt in part from empty-handed "friends" or scammers looking for a rich target. 

File photo of number balls for a lottery drawing. 

File photo of number balls for a lottery drawing. 

Photo Credit: Pixabay/ Alejandro Garay

If You Won The Lottery, Do You Think You Could Keep It A Secret?
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If You Won The Lottery, Do You Think You Could Keep It A Secret?

  • Yes
  • No
  • I wouldn't want to

In Massachusetts, winners must divulge their names and pose with novelty checks boasting their jackpot amount unless they create a trust to collect their cash.

Attorney David Spillane, a partner at the Quincy-based law firm SKB Attorneys, who's done nearly 100 of these trusts, connected us with some of those winners who chose to keep their paydays a secret to see what life was like as an undercover lottery winner. 

We sent them a questionnaire asking how their lives have changed since the big win. 

One of the biggest commonalities we noticed is they are much more giving of their money to causes and people they believe in even if they are doing it anonymously.

Winner A, a man in his 60s in Hampden County, said he won $4 million in 2019. He chose the 20-year annuity, which pays him about $148,000 after taxes annually. He told a select group of friends and family, and thankfully nothing has changed between them, he wrote. 

He still works a job and says his life hasn't changed much since his big win. Other than his ability to help his family and "pay it forward" to those in need. 

I am happier because I feel secure in paying my bills, I am able to enjoy life knowing I can help my children & donate to others. (When I was 17 years old I worked across the street from a food pantry and would see people line up daily, that experience left a huge sadness on me, I am now in my 60’s, and that sadness never left me. Since I received my blessing, my choice was to pay it forward yearly to that very same food pantry, along with other donations to vets, cancer societies and animals in need). 

His first big purchase was a reliable car, some home renovations, and giving to charities he cared for. 

Winner B, of Stoneham, who won $1 million in 2019 shortly after retiring, says they tip "seriously better" now than before. 

Winner B only told their partner about the win and has been able to keep it secret from everyone else. She had retired just before her payday, adding to their nest egg. 

They also took the 20-year annuity, which equals about $36,500 annually after taxes. "... An extra $100 a day," they said. Their first big purchase with the money was a trip to England, but other than that, the money hasn't impacted their lives as much as people may think. 

"I have less financial stress, but l was happy before and after," they said in an answer to our questionnaire. 

Winner C, of Shrewsbury, took the lump sum payment from their $1 million win earlier this year. After taxes and fees, they walked away with $461,500 — less than half of what they "won." It's something they found surprising about winning the lottery. 

I found it surprising that if you take the lump sum how much the lottery takes off the top and then in taxes. This isn't including what I'll be taxed on my income next year. I don't think people realize that if you win a million dollars you don't get close to a million after the lump sum penalty and taxes. 

Winner C kept the win a secret from everyone but their fiancee. 

They still work the same job they did before the win, but they're less stressed about making the full 40 hours each week. They don't panic about leaving work early to make an appointment like they did before and missing out on the hours.   

Winner C used the money to pay down debts and make some sensible investments. 

"I've put some of the money in a CD and used some of it to pay off a credit card bill, my car insurance, and house insurance for the year," they said in the Daily Voice questionnaire. 

Their life has gotten easier since the win, but they wouldn't say they are "happier." 

"I'm definitely a lot less stressed about where the money to pay my bills is going to come from," they wrote. "Or if I want to go out to dinner, play golf, or buy something I'm not worried about how I'm going to pay for it."

Interestingly, they all still play the lottery in the same way they did before. Each said they still buy scratch-off tickets or choose numbers for drawings just as they did before their wins. 

Do you think you could keep your lottery win a secret? 

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