• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia
LifestyleMassachusetts

A father and son duo who laundered over $20 million from 14,000 winning lottery tickets over a decade are going to prison

By
The Associated Press
The Associated Press
Down Arrow Button Icon
By
The Associated Press
The Associated Press
Down Arrow Button Icon
May 23, 2023, 11:42 AM ET
Lottery ticket
A shopper scratches a lottery ticket at Tan-Thang Market on Broadway in Chelsea, Mass. on June 4, 2014. Jessica Rinaldi/The Boston Globe via Getty Images

A father and son from Massachusetts have both been sent to prison for running an elaborate lottery fraud scheme designed to enrich themselves and help prize winners avoid paying taxes on their windfall, prosecutors said.

Recommended Video

Ali Jaafar, 63, and Yousef Jaafar, 29, both of Watertown, cashed in 14,000 winning lottery tickets over a roughly 10-year period, laundered more than $20 million in proceeds, and then lied on their tax returns to cheat the IRS out of about $6 million, the U.S. attorney’s office in Boston announced Monday.

The Jaafars purchased winning lottery tickets at a discount from people who wanted to avoid identification by the state lottery commission, which withholds taxes and outstanding child support payments from payouts.

After purchasing the tickets, using the stores that sold them as go-betweens, the Jaafars claimed the full prize amount. Although they reported the winnings on their tax returns, they also claimed equivalent fake gambling losses as an offset to avoid federal income taxes, prosecutors said.

Ali Jaafar was sentenced to five years in prison. Yousef Jaafar received a sentence of more than four years. They were also ordered to pay $6 million in restitution and forfeit the profits from their scheme.

They were convicted in December of conspiracy to defraud the IRS, conspiracy to commit money laundering, and filing a false tax return.

Mohamed Jaafar, another of Ali Jaafar’s sons, pleaded guilty to his role in the scheme in November and awaits sentencing.

The defendants paid the owners of dozens of stores that sell lottery tickets to facilitate the transactions, and the state lottery commission is in the process of revoking or suspending the licenses of more than 40 lottery agents, authorities said.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
About the Author
By The Associated Press
See full bioRight Arrow Button Icon

Latest in Lifestyle

HealthAffordable Care Act (ACA)
A Wisconsin couple was paying $2 a month for an ACA health plan. But as subsidies expire, it’s soaring to $1,600, forcing them to downgrade
By Ali Swenson and The Associated PressDecember 13, 2025
3 hours ago
Julian Braithwaite is the Director General of the International Alliance for Responsible Drinking
CommentaryProductivity
Gen Z is drinking 20% less than Millennials. Productivity is rising. Coincidence? Not quite
By Julian BraithwaiteDecember 13, 2025
4 hours ago
Nicholas Thompson
C-SuiteBook Excerpt
I took over one of the most prestigious media firms while training for an ultramarathon. Here’s what I learned becoming CEO of The Atlantic
By Nicholas ThompsonDecember 13, 2025
6 hours ago
Sarandos
Arts & EntertainmentM&A
It’s a sequel, it’s a remake, it’s a reboot: Lawyers grow wistful for old corporate rumbles as Paramount, Netflix fight for Warner
By Nick LichtenbergDecember 13, 2025
7 hours ago
Healthmeal delivery
Factor Meals Review 2025: Tester Approved
By Christina SnyderDecember 12, 2025
21 hours ago
Donald Trump
HealthHealth Insurance
‘Tragedy in the making’: Top healthcare exec on why insurance will spike to subsidize a tax cut to millionaires and billionaires
By Nick LichtenbergDecember 12, 2025
22 hours ago

Most Popular

placeholder alt text
Economy
Tariffs are taxes and they were used to finance the federal government until the 1913 income tax. A top economist breaks it down
By Kent JonesDecember 12, 2025
1 day ago
placeholder alt text
Success
Apple cofounder Ronald Wayne sold his 10% stake for $800 in 1976—today it’d be worth up to $400 billion
By Preston ForeDecember 12, 2025
1 day ago
placeholder alt text
Success
40% of Stanford undergrads receive disability accommodations—but it’s become a college-wide phenomenon as Gen Z try to succeed in the current climate
By Preston ForeDecember 12, 2025
1 day ago
placeholder alt text
Economy
For the first time since Trump’s tariff rollout, import tax revenue has fallen, threatening his lofty plans to slash the $38 trillion national debt
By Sasha RogelbergDecember 12, 2025
22 hours ago
placeholder alt text
Economy
The Fed just ‘Trump-proofed’ itself with a unanimous move to preempt a potential leadership shake-up
By Jason MaDecember 12, 2025
21 hours ago
placeholder alt text
Success
At 18, doctors gave him three hours to live. He played video games from his hospital bed—and now, he’s built a $10 million-a-year video game studio
By Preston ForeDecember 10, 2025
3 days ago
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • Future 50
  • World’s Most Admired Companies
  • See All Rankings
Sections
  • Finance
  • Leadership
  • Success
  • Tech
  • Asia
  • Europe
  • Environment
  • Fortune Crypto
  • Health
  • Retail
  • Lifestyle
  • Politics
  • Newsletters
  • Magazine
  • Features
  • Commentary
  • Mpw
  • CEO Initiative
  • Conferences
  • Personal Finance
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
About Us
  • About Us
  • Editorial Calendar
  • Press Center
  • Work At Fortune
  • Diversity And Inclusion
  • Terms And Conditions
  • Site Map

© 2025 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.