Raj Rajaratnam was one of the highest-profile insider-trading targets of former U.S. Attorney Preet Bharara following the 2008 financial collapse.
Bharara successfully prosecuted Rajaratnam for bagging $63.8 million in illicit profits from 2003 to 2009, trading in such stocks as eBay, Goldman Sachs and Google. A federal judge sentenced Rajaratnam to 11 years, the longest prison sentence ever imposed on an insider-trading convict.
Rajaratnam got many of his tips from former Goldman Sachs Group Inc. director Rajat Gupta, who was also prosecuted. They were longtime business associates and even played bridge and chess together in prison.
From a law enforcement perspective, the case was groundbreaking. Prosecutors used court-authorized wiretaps, a weapon more commonly associated with mobsters and drug dealers, to capture Rajaratnam discussing corporate secrets with his sources.
In one particularly damaging episode, Gupta called Rajaratnam shortly after a Goldman board meeting in September 2008 and tipped him that Warren Buffett’s Berkshire Hathaway was about to invest $5 billion in Goldman.
According to federal prosecutors, Rajaratnam and others at Galleon made more than $1 million from the tip.
Gupta later tipped him that Goldman was losing money for the quarter, helping Rajaratnam avoid millions of dollars in losses.
Rajaratnam came to the U.S. from Sri Lanka and founded Galleon Group, a hedge fund that at one time managed about $7 billion in assets and employed 180 people.
“Raj Rajaratnam stood at the summit of Wall Street, commanding his own financial empire,” Bharara said following the judge’s ruling. “Mr. Rajaratnam stood convicted 14 times over of felonies, his empire exposed as a web of fraud and corruption that entangled many. … It is a sad conclusion to what once seemed to be a glittering story.”
In addition to his prison sentence, a judge ordered Rajaratnam to forfeit $53.8 million and pay a $10 million criminal fine.
But life for Rajatnam went on, even behind bars.
“I went to bed overnight with a clear conscience and slept well,” Rajaratnam said in a 2021 interview with Forbes. “I felt I cleared my name but the jury saw it different. When they did, I walked into prison with my head high.”
A federal correction officer saw to it that Rajaratnam had an easy prison stay. William S. Tidwell, 50, of Keene, New Hampshire, pleaded guilty to taking $90,000 in benefits and getting a $50,000 loan from an “ultra-high net worth” inmate, identified as Rajaratnam.
Tidwell was sentenced to two years in prison in 2024. Rajaratnam was not charged in that case and he was released in 2019 after serving nearly eight years.
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Uneven Justice
After serving his time, Rajaranam published a woe-is-me memoir, “Uneven Justice,” in 2021, alleging prosecutorial overreach. Instead of getting a fair trial, he claims he was scapegoated for the 2008 financial crisis.
He used the charity defense in proclaiming his innocence, as if people who do good things would never do bad things.
“I just want to correct you on one thing,” he said in a 2021 CNBC interview. “I did not make a single cent. If everything I did was illegal, the money went to the investors. Right? It didn’t come to Raj Rajaratnam’s pocket. I gave more to charity than what was alleged that I was made. So how can you call me greedy?”
Back in business
Rajaratnam is barred for life from managing investors’ money, but after prison he established Synamon Global, a New York family office that manages his own fortune.
By 2022, about 18 employees and consultants were working with the operation as Rajaratnam traded stocks, invested in real estate and hunted for other opportunities.
Synamon Global has invested in information technology, agriculture, food processing and manufacturing there, according to Lanka Business Online.
In July 2025, Rajaratnam personally led a Synamon delegation to the University of Vavuniya to discuss entrepreneurship, internships and closer ties between the university and private industry.
Rajaratnam has also built a home in Jaffna, where he spends his winters, according to TamilCulture. Through Synamon, he has been putting money into agriculture, fishing and manufacturing in northern Sri Lanka while supporting technology entrepreneurs through Yarl IT Hub, which aimes to “transform Northern Sri Lanka into a thriving innovation ecosystem.”
These days, Rajaratnam says he has entered what he calls his “JOMO” phase – the joy of missing out – living more quietly, investing his money and giving some of it away.
His philosophy has changed enough that he now offers another maxim: “Only idiots die rich.”
The Raj Rajaratnam Foundation claims he has donated tens of millions of dollars over the years to causes ranging from education to disaster relief.
And in an irony almost too good to invent, one of the foundation’s stated pillars is “Good Governance and Economic Development,” including support for nongovernmental organizations working to establish “corporate accountability” and implement “anti-corruption measures.”
For all his philanthropy, there is at least one possession Rajaratnam isn’t ready to give away: His purported innocence.
More than 15 years after a federal jury convicted him on all 14 counts, Rajaratnam continues to portray himself as the victim of prosecutors who misunderstood Wall Street and made him a scapegoat for the financial crisis.
“I respect the verdict of the jury,” he told CNN in 2022. “But I don’t agree with it.”