Ivan Boesky Scandal: Jailed For Insider Trading In The 1980s


The mid-1980s witnessed a financial earthquake on Wall Street, an epic tale of wealth, ambition, and the treacherous underbelly of greed. The Ivan Boesky insider trading scandal unfolded as a cautionary narrative, where fortunes were both made and shattered. It all began with the accusation of a modest stockbroker, Michael Milken, who alleged that Ivan Boesky, a titan in the financial world, had tipped him off about impending mergers. Boesky’s alleged scheme involved purchasing shares in companies considering deals with his own firm, a tactic that triggered rumors and sent stock prices on a rollercoaster ride. Milken initially sought a $3 million settlement, but negotiations led to a remarkable agreement that reads like a Wall Street thriller. It’s a story that transcends the financial realm, encapsulating ambition, betrayal, and moral reckoning in a world where fortunes can be amassed and lost in the blink of an eye.

How Did Ivan Boesky Make His Money?

Ivan Boesky

Ivan Boesky made his money through a combination of roles in the financial world, including stock trading, investments, and involvement in the securities industry. He began his career on Wall Street as a stockbroker at a young age, gaining early exposure to the world of finance. Later, he worked at prominent financial institutions such as Merrill Lynch & Company, where he became a partner in the investment banking division.

Boesky’s significant wealth, however, came from his involvement in stock trading and investment activities, often marked by controversial practices. He engaged in insider trading, which involved obtaining and using confidential, nonpublic information about publicly traded companies to his advantage. By making strategic stock trades based on this insider information, Boesky could generate substantial profits.

His involvement in insider trading led to his arrest, conviction, and imprisonment in 1987, but not before he had amassed considerable wealth through these unethical practices. Although his actions ultimately resulted in legal consequences and a prison sentence, Ivan Boesky’s name remains closely associated with the insider trading scandal of the 1980s, a significant chapter in the history of Wall Street.

A Few Of The Ivan Boesky Scandal’s Players

Dennis Levine

American Wall Street arbitrageur Dennis Levine was the initial high-profile suspect in the Ivan Boesky insider trading scandal. In 1986, the authorities found him guilty of insider trading, and he received a two-year prison term, a fine of $362,000, and had his securities licenses revoked.

Martin Siegel 

Martin Siegel, a banker and financial advisor, along with Ivan Boesky, faced accusations of engaging in insider trading. Boesky claimed that Siegel gave him confidential information, which Boesky used to make millions.

Richard Wigton

Trader Richard Wigton and his partner Ivan Boesky faced accusations of insider trading. When they discovered that Boesky had given inside information to Wigton about a potential takeover of the USX Corporation, Wigton became embroiled in the scandal.

David Brown

Kidder Peabody & Co. executive David Brown was a suspect in the 1986 Ivan Boesky scandal. Claims stated that Brown had provided Boesky with access to proprietary information that Boesky had used to make lucrative trades.

How Did They Catch Ivan Boesky?

In August 1982, Ivan Boesky was arrested for insider trading

In August 1982, Ivan Boesky was arrested for insider trading.

Ivan Boesky’s downfall and subsequent arrest were the results of a five-month-long investigation by the U.S. Attorney’s office in New York. The government had gathered substantial evidence pointing to his involvement in illegal insider trading activities, especially within what they referred to as a “buddy system. In this system, Boesky shared non-public information with Michael Milken and other executives at Drexel Burnham Lambert, a major financial institution at the time. The key elements of how they caught Ivan Boesky include:


he investigation into Boesky’s activities began in 1982 and spanned several months. It aimed to uncover evidence of illegal trading based on advanced knowledge of future earnings.

Government Allegations 

The government alleged that Boesky had participated in sharing non-public information, which he and his associates used to trade stocks with an unfair advantage. This practice violated U.S. securities laws.

Guilty Plea 

Boesky eventually pleaded guilty to the charges against him. He admitted to six counts of securities fraud and one count of conspiracy to commit securities fraud.


In 1983, Boesky was sentenced to six months in jail and fined $1 million after being convicted by a jury. However, he served only three months in federal prison due to good behavior.

Probation and Monitoring 

Following his release, Boesky entered a three-year probationary period. As part of his probation, he had to wear an electronic monitoring device that could be placed on his ankle if necessary.

Testimony and Informants 

The government’s case relied on the testimony of several individuals, including Michael Milken and James C. Smith, who had knowledge of Boesky’s insider trading activities and were willing to cooperate with federal authorities.

Where Is Ivan Boesky Today And How Much Is He Worth?

Ivan Boesky is 85 now.

Shortly after being released from prison, he spent his time involved in projects that aimed to help the homeless. He has been primarily out of the spotlight. He currently lives in La Jolla, California quietly. The $23 million from his divorce settlement in 1991 certainly helps.

Throughout the 80s, Boesky was a well-known arbitrage specialist lovingly called Ivan the Terrible after the Viking. His fortune far exceeded $200 million according to some estimates. It was mainly due to betting on mergers and takeovers he was aware of.

Boesky has since returned to Wall Street where he now works as an advisor for hedge funds, private equity firms, and venture capital firms. He has also returned to writing books about financial markets, including several on insider trading. He is currently worth around $150 million according to Forbes magazine, making him one of America’s richest people.

Lucrative 80s: Wall Street’s Explosive Investing

Wall Street's Ivan Boesky in New York City, October 1984
Wall Street’s Ivan Boesky in New York City, October 1984.

An Era of Deregulation

The investment market in the 1980s was a dynamic and fast-paced arena characterized by high risk and even higher rewards. It was an era fueled by a lack of regulation, where financial opportunities seemed boundless. Ivan Boesky, known as “the Bear” for his staunch anti-regulation stance, rose to prominence in this environment, leveraging the newfound financial freedoms to his advantage.

Boesky’s Meteoric Rise

During this period, Ivan Boesky was amassing a staggering annual income of $2 million. Teaming up with his assistant, Michael Milken, they navigated the investment landscape with almost unrestricted access to valuable company information. Their strategy was simple yet effective: when other investors grew jittery about impending earnings reports, Boesky and Milken would swiftly sell their shares before public disclosure. This approach yielded substantial profits and allowed them to accumulate significant stakes in well-known companies.

A Regulatory Backlash

The lucrative 80s eventually gave way to a regulatory response. The passage of the Economic Growth and Tax Relief Act of 1981 (EGTRRA) effectively outlawed insider trading in specific industries deemed “too big to fail. This category encompasses banks, brokerages, securities dealers, insurance companies, and publicly traded firms. The Securities and Exchange Commission (SEC) intensified efforts to curb insider trading, significantly reshaping Wall Street’s dynamics.

The Dark Side of Prosperity

However, amid the prosperity, the 1980s also harbored a darker side. Market manipulation, insider trading, and financial wrongdoing came to the forefront. Figures like Ivan Boesky and Michael Milken faced convictions for their involvement in these illicit trading activities, underscoring the necessity for more stringent regulations.

Legacies and Reforms

In the aftermath of these scandals, Congress enacted the Sarbanes-Oxley Act, imposing heavier penalties for insider trading and demanding greater transparency in financial disclosures by publicly traded companies. People remember the 1980s as a period of both unparalleled opportunity and excess, where the financial world witnessed a convergence of fortunes and moral lapses, leading to the coining of the term “white-collar criminals”. The legacy of the 1980s is a multifaceted narrative, symbolizing a time of remarkable wealth creation and simultaneous ethical transgressions that left an indelible mark on Wall Street.


What Laws Did Ivan Boesky Break?

Boesky violated the Securities and Exchange Commission’s (SEC) rules that prohibited trading securities based on insider information. He was also charged with filing a false statement with the SEC, as he had knowingly lied about his involvement in the trading activities. Ivan Boesky was given a sentence of three years in prison and a fine of one hundred million dollars as retribution for his illegal insider trading operations.

What was the Ivan Boesky scandal?

The Ivan Boesky scandal was a major financial scandal that took place in the 1980s. Wall Street insider trader Boesky was arrested and convicted of illegally profiting from insider trading.

How was Ivan Boesky involved in insider trading?

Ivan Boesky was a Wall Street insider trader who illegally profited from trading on information he had obtained from company insiders. He used this information to make investments and generate significant profits. 

What was the outcome of the Ivan Boesky scandal?

Ivan Boesky was sentenced to three years in prison and fined $100 million for his involvement in insider trading. He was also barred from ever working in the securities industry again. 

How did the Ivan Boesky scandal affect the stock market?

The Ivan Boesky scandal had a significant impact on the stock market. It caused a great deal of uncertainty and distrust, and many investors were reluctant to invest in stocks. Additionally, the scandal resulted in a series of laws and regulations to prevent insider trading.