Round tripping, a deceptive financial maneuver that involves the repetitive buying and selling of the same or similar financial assets, often between related entities, is a practice that can mislead investors about a company's financial health or generate artificial revenue. This deceptive nature underscores the importance for investors to remain cautious, vigilant, and empowered with the knowledge to detect such practices, thereby giving them a sense of control and empowerment in the financial landscape.
Round-trip trading, in essence, is the unethical practice of repeatedly buying and selling shares of the same security multiple times. This deceptive maneuver is designed to mislead observers into believing that the security is in higher demand than it actually is, thereby creating a false impression of financial health.

It's crucial to understand that 'churning' behavior, which involves the repetitive buying and selling of securities, differs from the legal open and close transactions of day traders or ordinary investors. While every investor ultimately completes a round trip when they buy and later sell a security, the key difference lies in the intent behind these transactions.
Deceptive round-trip trading is designed to deceive, whereas legitimate trading is based on market conditions and informed investment strategies. Round tripping involves a series of transactions in which funds or assets are transferred from one entity to another and then back to the original entity, often through intermediaries or shell companies.
The main purpose is to inflate financial figures, create a false appearance of increased business activity, or manipulate financial statements. It can occur in various forms and across different industries, including accounting, trading, and capital markets.
Where there are instances in which the rapid buying and selling of stocks can be a legitimate practice, it is classified as unethical and illegal in many cases. If you're suspected of illegal round-tripping in the finance world, you could be subject to a range of federal criminal charges with the potential for severe penalties.
How Round Tripping Works
Round-trip trading is an attempt to create the appearance of a high volume of trades, without the company experiencing an increase in income or earnings. These types of trades can be completed by a single trader selling and purchasing the security on the same trading day, or by two companies buying and selling securities to each other. This practice is also known as churning or making wash trades.
Round tripping typically involves a series of coordinated transactions executed with no genuine business purpose. The essence of the scheme is simple in its design, but its complexity in execution can obscure it.
It can be the work of one or more people or entities who sell and re-buy shares of securities in a rapid-fire manner, or it can occur when one party sells shares to another, agreeing in advance to buy them back either immediately or after a specified period. These transactions are usually engineered to:
- Inflate revenues,
- Misstate earnings,
- Evade taxes, or
- Manipulate stock prices.
Those participating in round tripping often design these transactions to avoid triggering scrutiny, but regulators and investigators are becoming increasingly adept at identifying red flags.
To illustrate, round-tripping played a significant role in falsely inflating the market capitalization of companies like Enron, CMS Energy, and Reliant Energy. These companies engaged in round-trip transactions to artificially boost their trading volumes and revenue figures. This deceptive practice contributed to the eventual collapse of Enron, leading to public scandal, criminal charges, and financial ruin for many. Similar instances of round-tripping have been observed in other industries and countries, highlighting the widespread nature of this deceptive practice.
Round-Trip Trading Explained
Round-trip trading can be easily confused with legitimate trading practices, such as the frequent round-trip trades made by pattern day traders. These traders typically execute many transactions on the same day.

However, they do have minimum standards that they must adhere to, such as maintaining at least $25,000 of account equity before completing these types of transactions, and reporting their net gains or losses from the transactions as income, rather than treating gains as investments and losses as expenses.
Another instance of acceptable round-trip trades is a swap trade, where institutions sell securities to another individual or institution, agreeing to repurchase the same amount at the same price in the future.
Commercial banks and financial institutions often engage in this type of trading through the use of derivative products. But the dynamics of this kind of trading do not inflate volume statistics or balance sheet values.
Why Round Tripping Is Illegal
Round-tripping becomes illegal when it is used to deceive, defraud, or manipulate. Financial markets rely on transparency and accuracy to function effectively.

When companies or individuals engage in such fraudulent activities, they undermine investor confidence, distort economic data, and jeopardize the integrity of the marketplace.
Emphasizing the role of transparency in financial markets can reassure investors and stakeholders about the robustness and integrity of the system, instilling a sense of trust and reassurance in the financial system.
For these reasons, federal regulators, such as the Securities and Exchange Commission (SEC) and the Department of Justice (DOJ), actively investigate and prosecute schemes involving round-tripping. Their vigilance and enforcement actions play a crucial role in maintaining the integrity of financial markets and protecting investors from such deceptive practices.
The reasons why round-tripping is a problem include the following:
- Misleading Financial Statements. Round-tripping often creates a misleading picture of a company's financial health and performance, potentially deceiving investors, creditors, and regulators.
- Market Manipulation. While trading, it can be used to create the illusion of higher trading volume or liquidity, which may potentially influence market prices and the behavior of investors.
- Tax Evasion. Certain types of round-tripping, particularly cross-border transactions, may be employed to evade taxes or launder money.
- Legal Risks. Companies that engage in round-tripping face significant legal penalties, including investigations, lawsuits, and financial penalties, as well as damage to their reputation and relationships with stakeholders.
Simply put, round-tripping is a deceptive practice that undermines the integrity of financial markets and can cause significant harm to unsuspecting investors and other stakeholders. This should raise concerns and increase awareness about the potential risks involved, underlining the urgency and seriousness of the issue.
Criminal Charges from Round Tripping
The legal repercussions of round-tripping can be severe. If suspected of engaging in this practice, individuals and entities may face federal charges, including wire fraud, tax fraud, securities fraud, and even RICO charges. These charges carry significant penalties, including hefty fines and potential imprisonment, highlighting the serious legal risks associated with round-tripping.
In addition to these penalties, companies and individuals involved in round-tripping may also face civil lawsuits, regulatory sanctions, and damage to their reputation and relationships with stakeholders. Let's review the possible criminal charges below:
- Wire Fraud (18 U.S.C. 1343): Using electronic communications to execute a fraudulent scheme, like round tripping, is typically prosecuted as wire fraud. Penalties include hefty fines and potential imprisonment.
- Securities Fraud (18 U.S.C. 1348): If the scheme involves misleading investors or falsifying information tied to securities, charges of securities fraud might apply. This is a grave offense under federal law.
- Tax Fraud: Using round-tripping as part of a strategy to evade taxes can violate a variety of tax-related statutes.
- RICO Charges: When executed in an organized manner as part of illegal international trading schemes, round tripping can be charged under the Racketeer Influenced and Corrupt Practices Act (RICO).
Criminal investigations for activities like these often span years and involve a highly detailed examination of financial records and insider communications.
Legitimate Uses of Round-Trip Trading
Not all instances of repetitive buying and selling are inherently illegal. Round-trip trading can occur in legitimate contexts, particularly in high-frequency trading and day trading, where short-term transactions are a standard part of market strategies.

Day traders, for example, may buy and sell the same security multiple times within a single trading session to capitalize on small price fluctuations. These practices are lawful when conducted transparently, thoroughly documented, and with no intent to defraud.
The key distinction lies in intent and disclosure. If the trades are executed in good faith, with no prearranged agreements to deceive others or manipulate market conditions, they typically remain legal.
However, because these transactions can appear to be illegal schemes on the surface, both regulators and law enforcement may scrutinize them. This is where misunderstandings arise, and individuals engaged in lawful trading activity may find themselves under investigation.
Mitigating Risks of Round Tripping
If you are accused of engaging in round-tripping, understanding the nature of the allegations and their legal implications is vital. The prosecution must prove elements such as intent to deceive or orchestrated fraud. Documenting the legitimate intent behind transactions, maintaining accurate records, and having legal representation experienced in these matters are key steps in your defense.
Allegations of round-tripping, whether stemming from genuine misconduct or misinterpretation of lawful practices, can carry serious consequences. With federal scrutiny at an all-time high, it is essential to operate transparently and ensure compliance with all applicable financial and trading regulations. If you find yourself under suspicion, it is essential to engage an experienced federal criminal defense attorney.
For more information, contact our federal criminal defense law firm, Eisner Gorin LLP, located in Los Angeles, California.
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