By Bradley Hope 

CHICAGO--One June morning in 2012, a college dropout whom securities traders call "The Russian" logged on to his computer and began trading Brent-crude futures on a London exchange from his skyscraper office here.

Over six hours, Igor Oystacher's computer sent roughly 23,000 commands, including thousands of buy and sell orders, according to correspondence from the exchange to his clearing firm reviewed by The Wall Street Journal. But he canceled many of those orders milliseconds after placing them, the documents show, in what the exchange alleges was part of a trading practice designed to trick other investors into buying and selling at artificially high or low prices.

Traders call the illegal bluffing tactic "spoofing," and they say it has long been used to manipulate prices of anything from stocks to bonds to futures. Exchanges and regulators have only recently begun clamping down.

The 33-year-old Mr. Oystacher referred inquiries to a spokesman for his firm, 3Red Group LLC, who declined to comment for this story. In his clearing firm's correspondence with the exchange, Mr. Oystacher--co-founder of Chicago-based 3Red and well known in the clubby world of Chicago trading--is quoted as saying his trading is based on "analytics, statistical modeling and relative value theories."

Mr. Oystacher's trading activities on that day and others have been the focus of investigations by the Commodity Futures Trading Commission, or CFTC, and several exchanges into whether he broke securities laws or committed fraud, according to court documents, exchange correspondence and interviews with current and former associates. One exchange, CME Group Inc., in November banned him from trading on that exchange for a month after alleging he engaged in spoofing behavior; he didn't admit or deny any rule violations in the case.

The Federal Bureau of Investigation and U.S. Attorney's Office in Chicago have made inquiries into the trading of 3Red, according to a person familiar with the inquiries. The FBI and U.S. Attorney decline to comment.

The 2010 Dodd-Frank financial-overhaul law outlawed spoofing, but the tactic is still being used to manipulate markets, traders say. "Spoofing is extremely toxic for the markets," says Benjamin Blander, a managing member of Radix Trading LLC in Chicago. "Anything that distorts the accuracy of prices is stealing money away from the correct allocation of resources."

CME, the world's largest futures exchange, put out rule clarifications in August 2014 intended to end spoofing. The second-largest, Intercontinental Exchange Inc., or ICE, followed suit last month.

The CFTC in November said CME should work more on identifying spoofing and said it took too long to bring enforcement actions. CME says it had already taken steps to address issues the CFTC raised, declining to comment further for this story. The CFTC and ICE decline to comment for this story.

The first criminal charges against an alleged spoofer were brought in October 2014 in Chicago. The Securities and Exchange Commission and CFTC have brought several civil spoofing cases since 2012.

Exchanges are wary of rushing investigations into market manipulation because they are among the most serious allegations they can make and are difficult to prove, says Craig Pirrong, a University of Houston finance professor. "They have to go through a huge amount of data and try to infer a trader's intent to manipulate the market."

Trader vs. trader

Spoofing is rapid-fire feinting. A spoofer might dupe other traders into thinking oil prices are falling, say, by offering to sell futures contracts at $45.03 a barrel when the market price is $45.05. After other sellers join in with offers at that lower price, the spoofer quickly pivots, canceling his sell order and instead buying at the $45.03 price he set with the fake bid.

The spoofer, who has now bought at two cents under the true market price, can later sell at a higher price--perhaps by spoofing again, pretending to place a buy order at $45.04 but selling instead after tricking rivals to follow. Repeated many times, spoofing can produce big profits.

Spoofing can be hard to define. There are many legitimate reasons to cancel orders. A trader might cancel after the market heads in an unexpected direction or when a news flash suggests a different trade is in order. Market-making firms continuously adjust and cancel orders as they monitor supply and demand for a particular security.

And some traders say it can be difficult to distinguish between illegal market manipulation and savvy tactics to conceal the size of an intended trade--a technique used by traders since financial markets' earliest days.

"There are stories going way back about the guys in the Chicago trading pits trying ways to disguise their trading or show their cards in a certain light," says Matt Simon, an analyst at the market-research firm Tabb Group. "It raises a question now about whether someone is engaging in legitimate market activity or clear market manipulation."

The full extent of spoofing isn't known, but traders say it is evident in how prices move every day in a range of stock, bond and futures markets. Many financial firms have developed software to detect spoofing so their traders don't get duped.

To look for spoofing, authorities typically use statistical analysis to determine if a trader's strategy relies on spoofing and examine emails and other communication for signs of intent to spoof.

Some recent enforcement focus has been on alleged spoofing by high-frequency traders, who rely on superfast computers and trading algorithms to rapidly enter orders.

In the Chicago criminal case that is pending, the U.S. Attorney last year charged Michael Coscia, a New Jersey high-frequency trader, in U.S. District Court with six counts of commodities fraud and six counts of spoofing in 2011. Prosecutors accused him of illegally earning $1.6 million from spoofing in the U.S. and Europe. He denied the charges and filed a motion to dismiss them, arguing that anti-spoofing laws are vague. The U.S. Attorney and a lawyer for Mr. Coscia declined to comment for this article.

Mr. Coscia separately paid $2.8 million and agreed to a one-year trading ban to settle CFTC allegations in 2013 of spoofing, according to CFTC documents. He didn't admit or deny the charges.

While Mr. Oystacher's company employs high-frequency traders, he primarily entered orders manually on his keyboard, documents show. A review of court documents and exchange correspondence and interviews with more than a dozen current and former associates of Mr. Oystacher's provide a look at his trading style and show how complicated investigations into spoofing can be.

Mr. Oystacher moved to the U.S. from Moscow, according to his Facebook page and people who know him. He entered Northwestern University in Evanston, Ill., in 1999 and dropped out after three quarters, a Northwestern spokesman says.

Soon after, he started an internship at Gelber Group LLC, a prominent Chicago trading firm that cultivated a laid-back atmosphere where traders often dressed in T-shirts and flip-flops, say people who knew him at the time. Brian Gelber, the firm's founder, declines to comment.

Mr. Oystacher stood out for his quick grasp of market psychology. "He was successful within a year of starting," a former Gelber trader says. "He was putting up numbers it takes people three or four years to get to when they are starting out."

His aggressive trading, often in stock-index futures, drew attention in the trading community, where some dubbed him "The Russian."

"He's been talked about for years," says John Lothian, a former Chicago futures broker who publishes an exchange-industry newsletter.

Within Gelber, he earned nicknames like "Snuggles" and "The Pig," although former colleagues say they aren't sure why. He had down periods: After the 2010 Flash Crash, when the Dow Jones Industrial Average fell nearly 1,000 points before recovering, he told friends he lost significant money on a series of trades.

He left Gelber in 2010. In 2013, the firm agreed to pay a $750,000 fine to the CFTC over orders in 2009 and 2010 that an unidentified trader entered and canceled, allegedly to affect the price of a stock-index future, a CFTC news release says. Gelber didn't admit or deny the charges in accepting the settlement.

In 2011, Mr. Oystacher and another Gelber trader, Edwin Johnson, started their own firm in temporary space in the old Chicago Board of Trade. They named it 3Red Group after the three red chairs they and another early employee used.

Mr. Oystacher continued to make an outsize mark on futures markets. On one day in 2012, for instance, he traded more than 80,000 E-Mini S&P 500 futures--a type of contract on the stock index--with a combined notional value of nearly $6 billion, trading records show. His trading could sway markets, traders say.

Mr. Oystacher's trades began to draw attention from exchanges and investigators. The CME determined that on several dates between December 2010 and July 2011 he entered large bids and offers for silver, gold, copper and crude futures he didn't intend to trade, according to a public CME disciplinary notice. He quickly canceled those orders, placing others on the opposite side of the market, the notice says.

Fined and banned

In November 2014, the CME fined him $150,000 and banned him from trading on the exchange during December 2014. Mr. Oystacher didn't admit or deny any rule violations in agreeing to the fine and trading ban, the CME notice says.

A separate investigation into his trading in Brent-crude futures on ICE's European futures exchange on June 19 and 20, 2012--including the 23,000 commands--gives a glimpse into his trading.

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Several days later, a market-oversight analyst from the exchange wrote to Mr. Oystacher's clearing firm, Advantage Futures LLC, asking for all documents and communications related to his trades and a "full explanation of the rationale behind the trade activity."

ICE provided an Excel spreadsheet showing a detailed history of instances where Mr. Oystacher entered and quickly canceled a bid or offer while simultaneously placing an opposite order. On June 19, Mr. Oystacher completed 430 such reversals--each could take a number of commands--and 167 the next day.

In a letter to ICE Europe, Advantage quoted Mr. Oystacher as saying that "we are clicking in response to what we are seeing," adding: "If we click quicker than most, it is a skill."

ICE said in a subsequent decision that it didn't accept the rationale, calling Mr. Oystacher's trades "manipulative behavior" and ordering him to cease "disorderly trading" on the exchange. Advantage declines to comment.

Similar investigations into his trading were opened in 2012 and 2013 by regulators from exchanges such as CBOE Holdings Inc. and what was formerly NYSE Euronext, according to court documents and correspondence from the exchanges viewed by the Journal. Those exchanges decline to comment. It isn't clear whether their investigations have concluded.

A falling-out between 3Red's co-founders led to the ouster of one of them, Mr. Johnson, in August 2013, according to court documents and people familiar with the dispute. Last year, he sued the law firm of Gardiner, Koch, Weisberg and Wrona in Cook County, Ill., circuit court for allegedly helping Mr. Oystacher push him out improperly, among other allegations.

According to the lawsuit, the CFTC began investigating the trading of Mr. Oystacher and 3Red in 2011. Among the exhibits is a 2013 letter from a senior CFTC trial attorney, Jon Kramer, including a subpoena for 3Red. Mr. Kramer declines to comment. The CFTC investigation is active, say people familiar with 3Red.

Mr. Johnson's suit said he became "especially concerned about spoofing" by Mr. Oystacher in June 2013 after numerous regulatory inquiries. The law firm in a statement denies its attorneys acted improperly, saying: "We believe that Johnson's suit is without merit."

In a motion to dismiss the case, Gardiner, Koch, Weisberg and Wrona said 3Red terminated Mr. Johnson for "theft, fraud, breach of fiduciary duty, embezzlement" and that his suit was attempting to "extort funds" from 3Red. Mr. Johnson, in response, denied those claims. His lawyers decline to comment.

The judge in November granted the motion to dismiss, without giving an explanation, and gave permission for Mr. Johnson to file an amended complaint.

The suit included a copy of a settlement Mr. Johnson entered with Mr. Oystacher soon after his departure, which granted Mr. Johnson an initial $200,000 and another $250,000 to be paid out monthly until August 2015. One stipulation: If regulators fined Mr. Oystacher or 3Red $1 million or more, or if Mr. Oystacher was banned from trading for five months or longer, payments would stop.

Amid the scrutiny, Mr. Oystacher has slowed trading, says someone who speaks with him regularly. "He knows he has a target on his back."

Michael Rothfeld contributed to this article.

Write to Bradley Hope at bradley.hope@wsj.com

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