A Boston Area Father And Son Scammed 14,000 Lottery Tickets Over A Nine Year Period After They Just Kept Winning!

This is a wild one... let's break it down. 

Ali Jaafar, 63, and Yousef Jaafar, 29, both of Watertown, were convicted of one count of conspiracy to defraud the Internal Revenue Service, one count of conspiracy to commit money laundering and one count each of filing a false tax return. U.S. District Court Judge Nathaniel M. Gorton scheduled sentencing for April 11, 2023 and April 13, 2023 for Ali Jaafar and Yousef Jaafar, respectively. Mohamed Jaafar, another of Ali Jaafar’s sons, who was also involved in the scheme, previously pleaded guilty to conspiracy to defraud the Internal Revenue Service on Nov. 4, 2022 and is scheduled to be sentenced on March 8, 2023. 

Essentially what this father and son did was find people who won the lottery, they would offer them to purchase winning lottery tickets from actual winners for cash, at a discount that was typically between 10-20 percent of each ticket's value, which allowed the ticket holders to avoid reporting the winnings on their tax returns – a scheme commonly known as "10-percenting."

They then would go to a random bodega or gas station and cash in the winnings and then INCLUDE THE WINNINGS ON THEIR TAXES and would offset is by claiming gambling losses and avoiding paying federal income tax. The family face up to five years in federal prison for this little stunt. 

Also the scope of how many tickets were involved...

Between 2011 and 2020, the defendants and their co-conspirators cashed more than 14,000 lottery tickets and claimed more than $20,000,000 in Massachusetts lottery winnings. Based upon their submitted lottery claims, in 2019, Ali Jaafar was the top individual lottery ticket casher for Massachusetts. Mohamed Jaafar was the third highest individual ticket casher and Yousef Jaafar was the fourth highest individual ticket casher. In total, the three family members received more than $1,200,000 in tax refunds by claiming other peoples’ lottery tickets as their own and then offsetting those winnings with fake gambling losses on their tax returns.

I have to say the ingenuity of coming up with such a scam is truly fascinating. Quite a scheme and only in America. The Jaffars probably trigged plenty of alerts when year after year they just continue having the most luck in the history of the world for almost a decade long period. And to think… maybe just do it a few times a month or something? They cashed TENS OF THOUSANDS of tickets. In the end, greed is not always good. 

This also reminds me of a more sinister scumbag from similar area, Boston gangster Whitey Bulger. One of the scams he used to pull was instead of creating a scheme, he'd just go up to people that won the lottery and say give me a huge piece or I'll kill you. I guess in the case of the Jaffars it wasn't all bad, just highly illegal and when you steal from the government, they will get it back. 

Some stories get weirder and weirder.

If you want more crime content, check out my podcast "The Sitdown" out weekly