News writer; Opinion columnist
The family that wins together, stays together…usually.
There are many different ways to create cherished memories with your siblings. From family vacations to game nights to standing by each other at a wedding, these moments are all more meaningful when shared with a brother or sister. However, some siblings managed to take things a step further and become lottery millionaires together.
Winning big with your co-workers or friends is one thing, but taking down a major jackpot with a close family member is like winning twice because not only did you get rich, but someone you (probably) love did too.
These are true stories of siblings who cashed in big jackpots together.
Win big. Win little.
Retired judge James Stoklas enjoyed a rags-to-riches story before he ever collected one cent from the lottery. He told reporters:
We grew up poor. There were coal bins, very small houses, and a metal shower. There was no bathtub or anything like that. Hot water was heated by coal.
However, he worked hard, spending ten years as a millwright at Bethlehem Steel in Pennsylvania before eventually getting into politics and the legal profession. He served as a district judge for 32 years before retiring from the bench.
I've pretty much seen anything from parking tickets to murder cases.
In March of 2016, he and his brother, Rob Stoklas, decided to treat themselves to a Florida fishing vacation where they hoped they'd catch the 'big one'.
While eating breakfast at the Dockside Sports Bar in the Florida Keys, James noticed a massive yacht resting in the harbor. He envied the luxury of the pleasure craft but thought he'd need to win the lottery ever to purchase something so nice.
It turns out he may have had a prophetic vision.
When the trip was over, James and Rob hopped into their motorhome for the big drive back to their home in the Leigh Valley. Before hitting the road, they stopped at the Tom Thumb convenience store in Marathon, FL, to purchase a bag of ice and $10 worth of Powerball tickets, which they split between them.
As it turned out, both brothers were winners, but only one of them managed to hook the big one. While Rob collected $7 with his ticket, James came up big with the numbers 12-13-44-52-62 and the Powerball 06 and won a $291 million jackpot.
He discovered he was a winner while eating breakfast at his local diner and decided to celebrate by paying the bill for everyone in the restaurant. After collecting his lump sum payout of $191 million, James said one of the first things he wanted to buy for himself was another trip to Florida. As for Rob? Maybe he can help purchase the bait for their next fishing trip.
Stocklas said of himself and his brother:
We used to always laugh about what we would do if we won the lottery. But we would just say, 'Dream on.' All I can say is that all this has been a whirlwind since Friday.
One major purchase that James says he will definitely make is to buy a handicap-accessible home for his son, Jimmy, who is legally blind and has a disability. Stocklas, a divorced father of two and grandfather of three, stated:
It's family. Family takes care of family. And now I can take care of my children the right way.
Twenty and counting
There are big families, and then there is the Enderson family. Sigrid Enderson has sixteen living brothers and sisters, as well as another brother who has since passed away.
Sigrid's mother, Flossie, would play the lottery faithfully, and she always told her kids that if she ever won big, she planned to split the prize between them.
After Flossie passed away in 2004, all of her children contributed money for her funeral expenses. When they saw that a small sum was left over, they decided to use the remaining amount to form a lottery pool and purchased tickets together in memory of their mother.
The family, which is primarily based in Ocean County, purchased a New Jersey Lottery Pick-6 jackpot ticket for a July 2014 drawing. Sigrid, who manages the pool, told reporters that she was shocked when she saw that one of their tickets matched the winning numbers in the drawing, and she won a jackpot worth $20.1 million.
I ran the ticket through the machine, and one said, See your cashier.
She told family members that so many clerks inspected the ticket that she thought she might have done something wrong until one of them finally said to her that her ticket was worth millions.
I started to cry, and I called my sister. I told her to come get me! I said 'I don't think I can make it, you got to come get me!'
Faith Schiabor, another of the siblings, recalled receiving a phone call from Sigrid to tell her about the winning ticket.
She called me and said, Are you sitting down? And I thought, my God, is somebody hurt? That was my first feeling. She said it's nothing bad. It's actually very, very good, but I need you to sit down right now. Then she told me, and I think I went into instant shock.
The win was especially sweet because at least three members of the extended family lost their homes in the devastation of Hurricane Sandy, and they plan to use some of the money to help with the rebuilding.
The family plans to split the prize 20 ways, with one share going to the children of the deceased sibling. They elected to take the lump sum payout, which amounts to approximately $10 million after taxes are paid. Sigrid purchased the ticket from a 7-11 in Fork Ridge.
I'll see you in court
If twenty siblings can successfully split a lottery prize, how is it that two sisters wound up suing each other over one?
One of the trickiest parts of purchasing lottery tickets with another person is enforcing verbal agreements when millions of dollars are at stake. Connecticut resident Rose Bakaysa thought she had her legal bases covered when she and her sister, Theresas Sokaitis, each signed a notarized agreement stating that whatever money they won gambling, they would split 50/50 with each other.
The sisters, both in their 80s, loved to gamble and frequently discussed what they would do if they ever hit the jackpot. The two would buy lottery tickets together and take regular road trips to gamble at the Foxwoods Resort casino in Mashantucket.
While they did occasionally win small prizes, they never made the big score they dreamed of. Sadly, the sisters had a falling out over a $200 loan that Theresa gave to Rose, which she claims her sister never paid back.
Shortly after a dispute over the money, Theresas says she tore up her copy of the gambling agreement and considered their gambling partnership over.
After the fight, Theresas continued to gamble, and along with her brother, she won $500,000 from a 2005 Powerball drawing. She gave $10,000 to Rose's daughter, but offered her sister nothing.
Rose learned of the win and demanded her half of the money, claiming she was owed it under the terms of their signed contract. When Theresas refused, Rose sued her, and their trial played out in a New Britain, CT courtroom.
In court testimony, the two sisters admitted that they had once been close and that Theresa had provided financial assistance to Rose and her six children on several occasions. They had previously shared money from gambling wins with each other, but Theresa claims she would frequently loan Rose money and never get paid back.
"I was tired of giving her money. I gave her money for everything," Bakaysa testified.
Sokaitis stated the following:
I told her I felt I deserved a share of the money, and she told me I wasn't going to get a dime. I said, 'I have a contract.' She said, 'I tore mine up.' I said, 'I didn't.v
Ultimately, after a drawn-out legal battle, a judge awarded Rose a share of Theresa's lottery prize.
Crazy eights
The birth of a child is always cause for celebration, and one Maryland family decided to celebrate the arrival of a new member with a unique tradition. Eight years ago, a group of four Maryland siblings celebrated the birth of one of their first children by purchasing a Multi-Match lottery ticket together.
While the ticket wasn't a winner, it sparked a new tradition for the brothers and sisters, and they established a family lottery pool together. For years, the siblings, who chose to remain anonymous, had purchased Multi-Match tickets from the Maryland Lottery without ever claiming a big winner, until one fateful day on June 30, 2025, they finally hit the jackpot.
The sister responsible for collecting the money and purchasing the tickets was on vacation in the resort town of Ocean City, where she bought the ticket for that week's drawing at a Food Lion. She scanned her ticket in the store, and instead of being told how much she won, she received a message that said 'Go to Lottery.'
She checked the ticket on her lottery app, and her eyes went wide when she saw that it was worth $1.8 million; however, because the drawing had two jackpot winners, the family collected $490,000 from the lump sum payout.
The siblings are all retired nurses or government workers, so even split four ways, they said the money will go a long way in improving their lives. They plan to purchase a new car, travel to Europe, and grow their savings.
Lucky numbers
Bonding activities are an essential part of staying close with the people we care about. For William Fralick and Pamela McClure, a brother and sister from Brockton, Mass, playing the lottery together was how they shared a mutual interest.
The pair bought tickets for the August 25, 2024, Lucky for Life lottery drawing. Although they purchased their tickets separately, they each played the exact numbers: 8-17-19-29-31, with a Lucky Ball of 12, which they said corresponded to the birthdays of different family members.
When they checked the winning numbers, they were shocked to see that they had picked every number correctly except for the Lucky Ball. Even with one miss, they would both collect $25,000 a year for the rest of their life. They each selected the one-time payout amount of $390,000 before taxes. Fralick told reporters that he plans to add his prize to his savings account, while McClure hasn't decided how to use her funds yet.
Fralick purchased his ticket at the Star Food Mart in Brockton, while his sister bought hers at a 7-11 in Abington. Both stores will receive $5,000 for selling winning tickets.
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