Former Enron CEO Jeff Skilling, right, leaves the Bob Casey U.S. Courthouse after the end of his fraud and conspiracy trial May 25, 2006 in Houston.
Photo by Dave Einsel—Getty Images
By Daniel Roberts
July 7, 2014

It may be strange to realize that five years have already passed since Bernard Madoff reported to prison in the summer of 2009.

Madoff, as the world knows, ran one of the grandest Ponzi schemes in history until the swindle began to unravel in 2008. He pleaded guilty to fraud, money laundering, perjury, and false filing with the SEC—but the story always seemed larger than the sum of the crimes.

Maybe it was because of the sheer enormity of the heist—the tabloids pegged the losses at $65 billion (though later assessments said the figure was wildly inflated). Or maybe it was the boldfaced names that he bilked, figures that ranged from NY Mets owner Fred Wilpon to the charitable foundation of Nobel Peace Prize-winner Elie Wiesel. (Wiesel’s charity reportedly lost more than $15 million.) Or maybe it was that Madoff, a former chairman of Nasdaq, had seemed for years to be a pillar of the community—or that the crime had gone on, unchecked, for so long, or that regulators had missed so many clues to the malfeasance along the way. Or maybe it was the way Judge Denny Chin described Madoff’s crimes (“extraordinarily evil”) or the sentence that he handed down: 150 years. But in any case, the Madoff case seemed to define a generation’s worth of white-collar crime in the U.S.: the signal sent out was that this type of thievery was BIG and RARE and, when caught, it would be PUNISHED to the maximum.

As it turns out, that’s hardly the case at all. White-collar crime—a rubric that includes not just Ponzi schemes, but also a bevy of financial misdeeds, from embezzlement to money laundering to racketeering to insider trading—is far more common than many think. “White-collar” offenses made up 9.4 percent of federal criminal cases prosecuted in 2012 (the most recent report available), according to the U.S. Attorney’s office. That figure was up from 8.8% in 2009.

And yet a much smaller share of this group actually serves time. As of June 19, just 5.9% of the federal inmate population is in prison for crimes related to extortion, fraud, bribery, counterfeiting, embezzlement, banking and insurance-related offenses, according to the Bureau of Prisons (BOP). For comparison, nearly half (49.8%) of the country’s 216,620 federal inmates have been locked up for drug offenses; 15.7 percent for arson or crimes related to weapons and explosives; and 10.4 percent for immigration-related offenses. (We’ve examined only federal crimes for this report; there may be a significant number of white-collar criminals in state prisons.)

More than half of the best-known white-collar inmates—names like Raj Rajaratnam and Raj Gupta, to throw out a couple—are in prison because of insider trading. Since the mid-2000s, the Securities and Exchange Commission and federal prosecutors have ramped up their investigations, and the evidence is beginning to show. Since August 2009, for example, U.S. Attorney Preet Bharara has charged 90 people with insider trading; out of those, 84 have been convicted of or pled guilty to crimes, and 62 of them have been sentenced.

Where are all these white-collar criminals? Well, start with Madoff. He’s in Butner, N.C. And whatever happened, you might ask, to all those other fraudsters, like Jeff Skilling, Bernie Ebbers, and John Rigas…? Those fellows are in Montgomery, Ala.; Oakdale, La.; and Allenwood, Pa., respectively.

Like you, dear reader, we have often wondered about where the major white-collar convicts of yesteryear have ended up, and wondered much else as well—like how much time they have left in prison, and what life on the inside is really like.

So we thought we’d kick off your summer with a little prison roundup. There are plenty of surprises, as we discovered. Two of the best known of this breed, for instance—Tyco’s Dennis Kozlowski and Qwest’s Joe Nacchio—were both released in the past two years. Another surprise (or not) is that there are no women on our list: Roomy Khan and Winifred Jiau, both sentenced for crimes related to the Galleon Group insider trading case, were released in June.

Many of these imprisoned gentlemen are in minimum or low-security institutions. But some are in medium-security, and one or two were unlucky enough to land in high-security prisons. A chasm of difference separates each level, it’s worth noting. The change just from minimum-security to low-security, for example, can mean, in some locations, the addition of barbed-wire fences.

Raj Rajaratnam and a few others are currently housed in administrative facilities. That doesn’t mean that their digs are cushy, however. “Administrative security” facilities like Devens (where Rajaratnam is located, in Ayer, Ma.) aren’t necessarily higher or lower security than other prisons, a BOP spokesperson explains. The administrative label simply means that the staff has to deal with inmates of all security levels. Higher-security inmates require a higher staff-to-inmate ratio. And at a medical center like Devens, that extra staff may not be security, but rather doctors and nurses.

Even minimum-security prisons are not places where you’d want to spend any extended amount of time. Just ask former Wall Street M&A lawyer Matthew Kluger, who in June 2012 was handed the longest-ever sentence for insider trading. He’s reading this feature on a computer monitor inside a federal prison in Morgantown, W.V. Kluger sat down with Fortune last month for a lengthy and candid chat about his daily life in prison. (See our related story: “LIFE BEHIND BARS: Matthew Kluger reveals all.”)

To flesh out the details of our gallery we used the inmate locator run by the BOP, as well as a range of other governmental sources. And while the list below is not comprehensive, chances are you’ll find more than a couple of names you recognize. (Regarding the scope of jail terms for each, we’ve included the term handed down originally in sentencing; many of those prison terms have since been shortened.)

Below, our top 10 ranking of financial crime all-stars—ranked from most infamous to least. Plus, the tales of 15 lesser-known prisoners to round out our 2014 summer white-collar gang.


1. Bernard L. Madoff, 76

In 2011, 14 pairs of Madoff's boxer shorts sold for $200 at auction.
TIMOTHY A. CLARY—AFP/Getty Images

Prison: Butner Medium I FCI — Butner, NC (security: medium)
Release date: 11/14/2139 (sentence: 150 years)
Former company: Bernard L. Madoff Investment Securities LLC
Pleaded guilty to: Securities fraud; investment adviser fraud; mail fraud; wire fraud; money laundering; making false statements; perjury; making false filings with the SEC; theft from employee benefit funds.

A scrappy market maker and former Nasdaq chairman, Madoff confessed to his sons that the billions he had managed were all a lie. In a Shakespearean twist, his sons turned him in. The ultimate loss to investors was eventually estimated at $18 billion (far less than the $65 billion floated in the tabloids when the ruse was discovered), and the liquidation of Madoff assets by a court-appointed trustee is still underway. The former Wall Street high roller, who once lived in a 4,000-square-foot Manhattan penthouse, has not had an easy time in prison, where he is serving the longest allowable sentence for his crimes. In 2010, his eldest son Mark hanged himself, and this year Madoff suffered a heart attack behind bars. Just last week, Madoff’s former accountant, Paul Konigsberg, pled guilty to falsifying records, becoming the 15th guilty plea or conviction in connection with Madoff’s scheme.


2. Jeffrey K. Skilling, 60

Jeffrey Skilling, convicted former Enron Corp. chief executive officer, arrives to the Bob Casey Federal Courthouse in Houston, Texas, U.S., on Friday, June 21, 2013. Skilling is set to appear in court to learn how much longer hell stay in prison for spearheading the fraud that destroyed the worlds largest energy trader. Photographer: Aaron M. Sprecher/Bloomberg via Getty Images
Bloomberg Bloomberg via Getty Images

Prison: Montgomery FPC — Montgomery, AL (security: minimum)
Release date: 2/21/2019 (sentence: 24 years; reduced to 14)
Former company: Enron Corporation
Convicted of: Conspiracy; securities fraud; insider trading; making false statements to auditors

Jeffrey Skilling, the chief executive officer of Enron from February to August 2001, is one of the biggest fish in the white-collar sea. The Houston-based Enron, a gas pipeline company turned trader/merchant electrical power company, was thriving when it went bankrupt in 2001. The collapse revealed a massive criminal scandal involving fraudulent transactions, insider trading and cover-ups, and the company’s top dogs—Skilling and Kenneth Lay, who had been CEO of the company since its founding in 1985 (and resumed in the role after Skilling’s resignation)—took most of the heat. Lay died after his conviction, but prior to his sentencing; his conviction was then automatically overturned due to the fact that he had no opportunity to appeal. In a controversial decision last year, Skilling’s sentence was reduced by 10 years.


3. Bernard J. Ebbers, 72

Former WorldCom Inc. CEO Bernard Ebbers leaves Manhattan Federal Court after a verdict was handed down in his fraud trial Tuesday, March 15, 2005. Ebbers was convicted of fraud charges in an $11 billion accounting scandal, conspiracy and filing false documents with regulators.
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Prison: Oakdale FCI — Oakdale, LA (security: low)
Release date: 7/4/2028 (sentence: 25 years)
Former company: WorldCom
Convicted of: Securities fraud; conspiracy; filing false reports with the SEC

Until a different Bernie emerged as an even bigger crook, Bernie Ebbers was perhaps the most famous white-collar criminal alive. The Canadian co-founder and CEO of telecom giant WorldCom was found guilty of false financial reporting and pinned for some $100 billion in losses. In 2009, our sister publication Time included Ebbers on its own list of the 10 most crooked CEOs.


4a. John J. Rigas, 89

John Rigas, founder and former chairman of Adelphia Communications Corp., arrives at Federal Court in New York, Wednesday, June 27, 2007.
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Prison: Allenwood Low FCI — Allenwood PA (security: low)
Release date: 1/23/2018 (sentence: 15 years)
Former company: Adelphia Communications
Convicted of: Conspiring to commit securities fraud; conspiring to commit bank fraud; conspiring to make falser statements in SEC filings; securities fraud; bank fraud.

Rigas and his brother Gus founded cable television company Adelphia in Philadelphia (get it?) in 1952. Rigas built the business up, took it public in 1986, and made a number of acquisitions. He even became majority owner of the Buffalo Sabres NHL franchise. But the company went bankrupt in 2002 when it revealed more than $2.3 billion in previously undisclosed debt. Rigas was accused of stealing money from the company and dispersing it among his family, as well as hiding debt and other key information. Five Adelphia officers were charged with various crimes, but only Rigas and his son Timothy were convicted. Prosecutors requested a 215-year sentence, but the elder Rigas got 15.


4b. Timothy J. Rigas, 58

Timothy Rigas, left, former vice chairman of Adelphia Business Solution Inc., arrives at Federal Court in New York with his wife, Wednesday, June 27, 2007
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Prison: Allenwood Low FCI — Allenwood, PA (security: low)
Release date: 6/3/2022 (sentence: 20 years)
Former company: Adelphia Communications
Convicted of: Conspiring to commit securities fraud; conspiring to commit bank fraud; conspiring to make falser statements in SEC filings; securities fraud; bank fraud.

The younger Rigas, Adelphia’s Chief Financial Officer, got a longer sentence (20 years) than his dad (15). The Rigases requested to be imprisoned close to Cloudersport, Penn., where the company was founded and where their families lived, but instead went to Butner, N.C. (where, you’ll see, many others on this list either started their sentences or still sit today). Among other vivid details in the court findings: when Adelphia was riding high (its businesses included a radio station, a sports network, and the Buffalo Sabres, among other things)—and when John and Timothy were apparently concealing the company’s huge debts—Timothy was spending a lot of company money on personal luxuries. Among them? More than 100 pairs of fancy slippers.


5. Robert Allen Stanford, 64

Indicted financier R. Allen Stanford, accused of leading a $7 billion investment fraud scheme, arrives at the Bob Casey Federal Courthouse in Houston, Texas, U.S., on Monday, March 5, 2012. Stanford "flushed" investor money away on failing businesses, yachts and cricket tournaments, prosecutors told jurors who began deliberations on whether the Texas financier led a massive Ponzi scheme
Getty Images

Prison: USP Coleman II — Sumpterville, FL (security: high)
Release date: 4/17/2105 (sentence: 110 years)
Former company: Stanford Investment Bank
Convicted of: Conspiracy to commit wire fraud; conspiracy to commit mail fraud; mail fraud; conspiracy to obstruct an SEC investigation; obstruction of an SEC investigation; conspiracy to commit money laundering.

Another notable Ponzi schemer who went unchecked, Texas-based R. Allen Stanford was giving investors higher-than-market returns for years before the authorities wised up to what was really going on: his Stanford Investment Bank was a $7 billion fraud. The jet-setting CEO and bodybuilder who had offices across the country, and dual citizenship in the U.S. and Antigua, is no longer flying around the world, but serving a sentence that will keep him in jail for the rest of his life.


6. Raj Rajaratnam, 57

Galleon Group founder Raj Rajaratnam exits Manhattan Federal Court after a sentencing hearing on October 13, 2011 in New York City. Rajaratnam was sentenced to eleven years in prison in a hedge fund insider trading scandal.
Mario Tama—Getty Images

Prison: Devens FMC — Ayer, MA (medical center)
Release date: 7/4/2021 (sentence: 11 years)
Former company: Galleon Group
Convicted of: Conspiracy to commit securities fraud; securities fraud

The assets managed by hedge fund Galleon Group—originally called the Needham Emerging Growth Partnership and created in 1992—were said to be worth some $7 billion in 2008, before the downturn cut that figure in half. But in 2009, Rajaratnam, who was previously regarded as an investment all-star, was arrested and charged with operating the biggest insider-trading scheme in U.S. history, estimated by U.S. Attorney Bharara to have resulted in more than $60 million in ill-gotten gains. Rajaratnam received an 11-year sentence in 2011, a record at that time for longest ever insider-trading conviction, as the FBI boasted in a press release. That distinction would soon be eclipsed by the sentence handed to M&A lawyer Matthew Kluger a year later (see No. 9).


7. Rajat K. Gupta, 65

Rajat Gupta, former Goldman Sachs Inc. director and former senior partner at McKinsey & Co., exits federal court in New York, U.S., on Friday, June 15, 2012. Gupta, 63, was convicted by a federal jury for leaking inside information to hedge-fund manager Raj Rajaratnam.
Getty Images

Prison: Devens FMC — Devens, MA (medical center)
Release date: 6/17/2016 (sentence: 2 years)
Former company: Goldman Sachs Group
Convicted of: Conspiracy to commit securities fraud; securities fraud

Gupta, a previously respected businessman who was CEO of McKinsey from 1994 to 2003, must rue the day he fell in with Raj Rajaratnam. Gupta, who sat on the boards of many companies including Goldman Sachs and P&G, was accused of sharing inside information with Rajaratnam that benefitted both men, to the tune of $23 million, the SEC said. After an initial sentence for insider trading and various appeals, Gupta at last had to report to prison in June and is slated to serve two years. He continues to claim he is innocent of the charges.


8. Barry J. Minkow, 48

Barry Minkow, pastor and head of the Fraud Discovery Institute, sits for a photo at the Community Bible Church in San Diego, California, U.S., on Friday, Feb., 27, 2009. The Fraud Discovery Institute, a San Diego-based licensed private investigator, was co-founded by Minkow, who served more than seven years in federal prison for fraud
Getty Images

Prison: Lexington FMC — Lexington, KY (security: administrative)
Release date: 6/6/2019 (sentence: 5 years in 2011 plus another 5 years in 2014)
Former company: ZZZZ Best; latest company: San Diego Community Bible Church
Pleaded guilty to: conspiracy to commit securities fraud (2011); embezzlement (2014)

The fascinating and ever-strange story of Barry Minkow was chronicled in grand fashion by Fortune in a 2012 feature story, “All-American Con Man.” Minkow, who was the perpetrator of a number of different scams (including a Ponzi scheme), ended up in prison in the 1980s, was paroled in the late ’90s—and then, in the early 2000s, began committing new financial frauds. He was caught operating a stock manipulation scheme in 2011 and was sentenced to five years. While already in custody, he admitted to misappropriating more than $3 million from the coffers of a church that had made him an executive officer, and for that he got another five years to add on to the sentence he was already serving. In a sense, Minkow, in and out of prison for more than two decades, serves as a symbol for this entire list.


9. Matthew H. Kluger, 53

Matthew Kluger, a former attorney with Wilson Sonsini Goodrich & Rosati, arrives at federal court in Newark, N.J. on June 4, 2012, for sentencing.
Photograph by Getty Images

Prison: Morgantown FCI — Morgantown, WV (security: minimum)
Release date: 2/2/2023 (sentence: 12 years)
Former company: Multiple law firms
Pleaded guilty to: Conspiracy to commit securities fraud; securities fraud; conspiracy to commit money laundering; obstruction of justice

Kluger was a hotshot M&A lawyer doing work for a number of big-deal firms such as Skadden, Arps, Slate, Meagher & Flom and Wilson, Sonsini, Goodrich & Rosati who was sharing information on upcoming mega-mergers with a middleman friend, broker Kenneth T. Robinson, who would in turn give the information to trader Garrett Bauer, who would cash in, make big money, and then hand cash (in $50 bills) to Robinson, who would split it with Kluger. All told, Kluger made a mere million or two from the scheme, but it sure cost him: 12 years, the longest ever sentence for insider trading. Bauer, the trader, who made closer to $30 million from their 17-year-long scheme, only got 9 years. (In April 2001, Robinson pleaded guilty to his role in the scheme and, after cooperating with authorities in the investigation, was sentenced to 27 months.)

Click here to read our candid prison interview with Kluger on life behind bars.


10. Garrett D. Bauer, 46

Garrett Bauer, a former trader with Lighthouse Financial Group LLC, arrives at federal court in Newark, New Jersey, U.S., on Monday, June 4, 2012.
Getty Images

Prison: Montgomery FPC — Montgomery, AL (security: minimum)
Release date: 5/13/2020 (sentence: 9 years)
Former company: Multiple investment firms
Pleaded guilty to: Conspiracy to commit securities fraud; securities fraud; conspiracy to commit money laundering; obstruction of justice

Bauer is a known name to anyone who followed the story of Matthew Kluger: while working as a proprietary trader for various trading groups, like RBC and Lighthouse Financial, Bauer was secretly getting advanced scoops thanks to Kluger. After some 17 years of passing secrets without getting caught, Bauer tried to walk away. It was then that their middleman, Kenneth Robinson, made a trade in his own name—a move that would ultimately bring down the entire trio.

Plus 15 inmates that aren’t quite household names…but maybe ought to be.


Samuel Israel III, 54

Prison: Butner Low FCI — Butner, NC (security: low)
Release date: 9/12/2027 (sentence: 22 years)
Former company: Bayou Hedge Fund Group
Pleaded guilty to: Conspiracy to commit investment adviser fraud and mail fraud; investment advisor fraud; mail fraud (2005); failing to surrender (2009)

Israel’s story is one of the wackiest of this whole bunch: the man behind Bayou Hedge Fund Group, launched in 1996, was thriving on Wall Street until 2004, when a bad bet on gold led to huge losses that Israel concealed through falsified accounting. When he was found out, arrested, and sentenced to 20 years, he faked his own suicide on the day he was supposed to report to prison and disappeared for over a month before turning himself in. Guy Lawson’s 2012 book Octopus is a fascinating read on Israel. Check back on fortune.com this winter, when we will post our own prison interview with Sam Israel.


Frederick C. Brandau, 69

Prison: FCI Coleman — Sumpterville, FL (security: medium)
Release date: 08/08/2047 (sentence: 55 years)
Former company: Financial Federated
Convicted of: Conspiracy to commit mail fraud; conspiracy to commit wire fraud; mail fraud; conspiracy to commit money laundering; money laundering.

This is about as cruel as financial crimes get: Frederick Brandau’s South Florida life insurance company specifically targeted the elderly and family members of the terminally ill, selling them policies but using the premium money to buy luxury items like boats and cars. The scheme was estimated to have cost his “customers” $117 million—with thousands of people paying for life insurance policies that never existed.


Marc S. Dreier, 64

Mark Dreier, founder and former managing partner of Dreier LLP, arrives for a sentencing hearing at Federal District Court in New York, U.S., on Monday, July 13, 2009. Marc Dreier, the New York law firm-founder, was sentenced to 20 years in prison for defrauding hedge funds of more than $400 million and stealing money from his clients.
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Prison: Sandstone FCI — Sandstone, MN (security: low)
Release date: 11/11/2026 (sentence: 20 years)
Former company: Dreier L.L.P.
Pleaded guilty to: Conspiracy to commit securities and wire fraud; wire fraud; money laundering

Attorney Marc Dreier’s law firm Dreier LLP, which he ran like a corporation rather than a traditional firm, turned out to be a Ponzi scheme that stole a total of $400 million, mostly from hedge funds, by selling them fake promissory notes. Dreier earned particular interest in the press at the time of his arrest thanks to juicy details like the celebrity clients (Justin Timberlake, Bill Cosby, and Jon Bon Jovi among them) that have come forward to file claims against him.


Timothy S. Durham, 51

Prison: McCreary USP — Pine Knot, KY (security: high)
Release date: 01/25/2056 (sentence: 50 years)
Former company: Fair Finance
Convicted of: Conspiracy to commit wire and securities fraud; wire fraud; securities fraud

Once the CEO of National Lampoon—yes, the media company responsible for movies like “Vacation”—Tim Durham’s Ohio-based investment business, Fair Finance, was a Ponzi scheme that tricked clients out of some $200 million. Some of the people Fair Finance cheated were local Ohio farmers who had put their life savings into the company’s coffers.


John P. Kinnucan, 57

Oregon based research consultant, John Kinnucan, is pictured in this booking photo provided by Multnomah County Jail to Reuters on February 17, 2012.
Reuters

Prison: Terminal Island FCI — San Pedro, CA (security: low)
Release date: 10/28/2015 (sentence: 4 years)
Former company: Broadband Research LLC
Pleaded guilty to: Conspiracy to commit securities fraud; securities fraud

Sometimes those at the center of a profitable criminal scheme are far from the public faces or high-up executives. John Kinnucan was just the president of a little-known investment research firm in Portland, but became a central focus in the business press in 2010 when he taunted the FBI and dared it to arrest him. Arrested Kinnucan was—for receiving inside information from employees of a wide range of companies, and then selling that information to his clients as though it were legitimate research. That’s slightly different from the usual form of insider trading you hear about—A tells B non-public information, B uses it to buy stock and make big money—but it’s insider trading nonetheless, and Kinnucan got 4 years, a relatively harsh sentence for his particular crimes. Just as with crime, taunting the authorities doesn’t pay.


Eduardo A. Masferrer, 65

Prison: Butner Low FCI — Butner, NC (security: low)
Release date: 6/27/2032 (sentence: 30 years)
Former company: Hamilton Bank
Convicted of: Bank and securities fraud

This Miami banker was living high on the hog and had built up a star reputation after moving from Panama to take over Hamilton Bank in 1989. It ended in 2002 when regulators seized his bank after he was accused of a $20 million bank fraud. Once widely known and well regarded for his philanthropy in the city, Masferrer got 30 years in prison for his deception.


Thomas J. Petters, 56

Prison: Leavenworth USP — Leavenworth, KS (security: medium)
Release date: 04/25/2052 (sentence: 50 years)
Former company: Petters Group Worldwide
Convicted of: Conspiracy to commit mail and wire fraud; mail fraud; conspiracy to commit money laundering; money laundering

The man whose company once owned Polaroid isn’t snapping any fun, white-bordered photos these days. Thomas Petters initially claimed in court he did not know about the fraud going on at Petters Group Worldwide, but the judge didn’t buy it. The company was deemed a $3.7 billion Ponzi scheme, and Petters got 50 years, though prosecutors had sought the 335-year maximum.


Lance K. Poulsen, 71

Lance Poulsen, former CEO of National Century Financial Enterprises, a health care financing firm being probed by federal authorities
The Washington Post—Getty Images

Prison: Coleman Low FCI — Sumterville, FL (security: low)
Release date: 12/4/2033 (sentence: 30 years)
Former company: National Century Financial Enterprises
Convicted of: Conspiracy; securities fraud; wire fraud; money laundering; witness tampering

Ohio-based National Century Financial Enterprises provided financing to healthcare outfits, like hospitals and clinics, until it collapsed in 2002 and was revealed as a fraud. The bankruptcy of NCFE caused the bankruptcy, in turn, of some 275 other health care facilities in what amounted to a $2.9 billion Ponzi scheme. Poulsen’s sentence (longer than Skilling, longer than Ebbers), which didn’t come until 2009, was cited at the time as a sign that Ponzi scheme sentences would get longer, and that has proven to be true.


Martin Sigillito, 65

Prison: Memphis FCI — Memphis, TN (security: medium)
Release date: 02/15/2047 (sentence: 40 years)
Former company: British Lending Program
Convicted of: Wire fraud; mail fraud; money laundering

This criminal was wearing a different kind of white collar: Sigillito was an Anglican bishop in St. Louis and respected pillar of the community who launched an investment business based on the promise of real estate developments in England. Sigillito would frequently fly to London on the pretense of making investments on behalf of his clients, but all was for show. The federal indictment alleged that Sigillito and his two co-conspirators stole more than $52 million through a Ponzi scheme that lasted nearly a decade.


Keith F. Simmons, 49

Prison: Lee USP — Pennington Gap, VA (security: high)
Release date: 07/09/2053 (sentence: 50 years)
Former company: Black Diamond Capital Solutions
Convicted of: Wire and securities fraud; money laundering

Another Ponzi schemer, Keith Simmons was accused of using his North Carolina hedge fund, Black Diamond, to fool investors and keep all the money. He led his clients to believe they were putting money into a foreign currency exchange, when in fact he was never investing it anywhere but his own pockets. Like with most Ponzi schemes, he fictionalized returns and reaped the riches until he got caught.


Joseph F. Skowron, 44

Joseph F. "Chip" Skowron, former fund manager with FrontPoint Partners LLC, arrives at federal court for a sentencing hearing in New York, U.S., on Friday, Nov. 18, 2011. Skowron, 42, a Yale University-educated physician from Greenwich, Connecticut, pleaded guilty in August to conspiring to commit securities fraud and obstruction of a federal investigation.
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Prison: McKean FCI — Lewis Run, PA (security: medium)
Release date: 5/14/2015 (sentence: 5 years)
Former company: FrontPoint Partners LLC
Pleaded guilty to: Conspiracy to engage in insider trading; obstruction of justice

Armed with a Yale medical degree, Joe Skowron was a resident at Harvard when he left the world of medicine to start a healthcare investment fund at FrontPoint Partners. But Dr. Skowron, who went by “Chip,” was receiving inside tips from Yves Benhamou, another doctor who was telling Skowron about the results of drug trials, allowing FrontPoint to buy or sell certain medical stocks at just the right time. Skowron got five years for his insider trading and will be out next year; his accomplice Benhamou was released from prison in 2010.


Robert Thompson (a.k.a. John Lawson), 48

Prison: Marion USP — Marion, IL (security: medium)
Release date: 12/29/2277 (sentence: 309 years)
Pleaded guilty to: Conspiracy; wire fraud; mail fraud; bank fraud; computer fraud; access device fraud; aggravated identity theft; money laundering; obstruction of justice

Thompson’s story is so zany that the FBI posted its own account of the fraudster on its website in 2010, citing him as an important example “for consumers and businesses who take the risk of sharing personal information over the telephone.” From inside a Louisiana prison, where Thompson had been jailed for a short time for fraud, he masterminded a huge operation involving identity theft and fraudulent credit card purchases. He did it all using the help of accomplices both inside and outside of prison—hence his current digs in Illinois, a facility specifically designed for inmates with a history of using communication methods to perpetrate further crimes.


Randall T. Treadwell, 56

Prison: Coleman Low FCI — Sumterville, FL (security: low)
Release date: 9/4/2027 (sentence: 25 years)
Former companies: Learn Waterhouse; Wealth Builders Club; Qwest International
Convicted of: Conspiracy; wire fraud

Not unlike the crimes of Martin Sigilitto, “religion was the lure,” as a 2005 Jacksonville Times-Union headline puts it, in Randall Treadwell’s Florida Ponzi scheme. Treadwell and his associated bilked $50 million from almost 2,000 clients with promises of 50% returns through various investment clubs. The schemes lasted for only a year, ending in 2004—but it was enough time for Treadwell to live like a king (with his own Jacksonville Jaguars luxury box) before it all came crashing down.


Steven E. Warshak, 48

Prison: Beckley FCI — Beaver, WV (security: medium)
Release date: 6/14/2016 (sentence: 25 years; reduced to 10)
Former company: Berkeley Premium Nutraceuticals
Convicted of: Bank fraud; mail fraud; money laundering

You may never have heard of Berkeley Premium Nutraceuticals, but perhaps you recall its prize product: Enzyte. In a 2009 feature, GQ called Steven Warshak, the man behind the company, “the Cincinnati boner king.” It turned out that Warshak was misrepresenting the business, laundering money from it, charging customer credit cards without authorization, and a host of other frauds and crimes. The erection-pill exec got a 25-year sentence for his fraud, but in 2011, a court cut 15 of those years off the term.


Sholam Weiss, 60

Prison: Otisville FCI — Otisville, NY (security: medium)
Release date: 11/23/2754 (sentence: 845 years; reduced to 835)
Former company: National Heritage Life Insurance
Convicted of: Racketeering; wire fraud; interstate transportation of stolen funds; money laundering

Here’s a name that may not be known to most Fortune readers, even though he perpetrated the largest insurance fraud in U.S. history, leading to the longest white-collar sentence in U.S. history. Sholam Weiss took over the National Heritage Life Insurance Co. in 1993 and proceeded to trick its elderly clients out of more than $450 million. Thousands of people lost their life savings due to Weiss’s scheme. In 1999, after his trial and before sentencing, Weiss fled to Austria, but was extradited back to the States, where he got a sentence of 845 years. In 2011, a judge reduced that sentence…by 10 years.

For a peek at life on the inside for one white-collar convict, see our candid prison interview with Matthew Kluger (Click here).

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