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Are You Guilty of Insider Trading?

Kathy Kristof, Contributing Editor, Kiplinger's Personal Finance

If you're an active investor who occasionally buys or sells a stock based on tips, you might be understandably nervous about ex-U.S. Rep. Chris Collins, who recently resigned from the House of Representatives before pleading guilty to insider trading charges.

While in office, the Republican congressman from New York fed information he received as a board member of biotechnology company Innate Immunotherapeutics to help his son and others avoid thousands of dollars in losses after one of the firm's drugs failed a clinical trial.

But it is perfectly legal (although potentially unwise) to trade on some tips that you hear or overhear. Illegal insider trading is all about facts and circumstances.

Here we offer you 10 situations that may or may not constitute illegal insider trading. Can you tell which ones might get you in trouble? Take our quiz and see.

1: You are standing in line at Starbucks, and a well-dressed couple in front of you is talking about retiring to Majorca after they sell their company. You recognize them as the founders of a publicly traded company and figure out that the deal hasn't yet been announced. You snap up as many shares as you can afford and make a killing when the takeover is announced. Is this insider trading?

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is A. A. Not insider trading

If this couple bought or sold shares -- or called you and tipped you off in private -- it would be a violation. But illegal insider trading requires that you not only trade on the basis of important nonpublic information, but that you also have some sort of duty to keep the information confidential. Former football coach Barry Switzer was sued for insider trading following a similar scenario in 1981, but he won the case because he had no duty to ignore a conversation he overheard in a public place.

2: You're a janitor at a major company. You hear members of the company's board convening outside the room you're cleaning and decide to hide in the closet. The board OKs a deal to sell the company for a fat premium to the current share price. You load up on the shares. Illegal insider trading?

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is B. B. Definitely insider trading

This is not a public place, and "you'd be in a position to understand that confidential information was being disclosed, which changes the calculus," says Andrew Stoltmann, a Chicago-based securities lawyer.

3: You hop in a cab at JFK and are startled by the driver's Armani suit and solid-gold pinkie ring. You learn that the driver is merely taking this shift as a favor for a friend. The driver is now happily retired, living on his investment portfolio. When you whine about your own, he says: "Look, I'll give you a break. Buy as much stock in Google as you can." You do. Insider trading?

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is A. A. Not insider trading

It may be unwise -- because the cab driver could be as clueless as you -- but you have no reason to believe he's telling you anything that's not public information.

4: Once again a cab driver is offering stock tips, but this time he mentions that his son is an attorney at Skadden, Arps, Slate, Meagher & Flom, a major law firm in the merger game. Insider trading?

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is C. C. Will draw SEC scrutiny, but maybe not a prison term

This could qualify as insider trading. It's all about whether you have reason to believe that you're receiving important, nonpublic information from a person who has a duty to keep that information private. The cab driver's trading would definitely be verboten. Yours is in a hard-to-defend gray area, Stoltmann says.

5: You read a few years back that executives at Countrywide Financial, the big mortgage lender, were unloading their stock. You decided that they must know something you didn't, so you followed suit and sold your shares, too. Now you worry that the Feds are going to come after you. Are you guilty of insider trading?

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is A. A. Not insider trading

...for you. For them, it may be insider trading. Executives can sell their own company's stock without running afoul of the rules as long as they're not trading based on information they haven't shared with the public. The SEC sued Countrywide's CEO, Angelo Mozilo, and several other insiders in 2009 (after the company had been acquired by Bank of America), alleging that they had improperly traded on undisclosed information about the evil lurking inside the company's loan portfolio. Mozilo, who netted some $140 million selling Countrywide stock before the company collapsed, eventually settled the suit without admitting or denying guilt by paying $67.5 million in fines and disgorging profits.
As for you: Mozilo's trades were disclosed in SEC filings and in numerous news stories. Trading based on publicly available information is perfectly legal.

6: A woman in your Bunco group says she's about to quit her job because she can't stand the strain of working in a medical office where all the patients are dying. Because of previous casual conversations, you know that patients in this office are involved in early trials of a new drug. You know what the drug is and who makes it. You sell short shares of the drug's developer, betting that the stock will fall in value. Did you violate insider-trading rules?

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is C. C. Will draw SEC scrutiny, but maybe not a prison term

This probably will not be counted as insider trading. Your playing partner is sharing information that's so general it can't be used to gauge whether the clinical trial will result in failure. Thus, the tip fails the materiality test. It's not significant enough to the company's stock price. And because the woman is just sharing information about the status of the office's patients and not the trial (including whether the ailing patients are taking the new drug or a placebo), no one appears to have a duty to keep quiet.

7: You are entrusted with confidential information that the company you work for has suffered a massive data breach. You purchase options in your company's stock ahead of its public announcement of the breach in order to profit when shares fall on the news.

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is B. B. Definitely insider trading

Sudhakar Reddy Bonthu, a former manager at Equifax, pleaded guilty in July 2018 to a charge of insider trading based on his purchases of put options ahead of Equifax's public announcement of its data breach. "Bonthu used confidential information to determine that his company had suffered a massive data breach and then violated company policy to illegally profit from it," said Richard Best, Director of the Securities and Exchange Commission's Atlanta Regional Office, in a statement. Bonthu realized a profit of more than $75,000 when shares in Equifax tumbled after it publicly disclosed the data breach on September 7, 2017.

8: Your broker calls and says you need to get out of ImClone Systems now because the CEO, who is also his client, is selling all his shares. Insider trading?

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is C. C. Will draw SEC scrutiny, but maybe not a prison term

The SEC filed suit against homemaking personality Martha Stewart in 2003 with these exact facts. Stewart did end up going to prison -- but not for insider trading. She was convicted of obstructing justice and lying to prosecutors. Stewart settled the SEC's insider-trading case, paying a fine and agreeing to never violate securities laws in the future. The settlement eliminated the need for a trial as well as a definitive answer about whether she had "a duty" to ignore the tip. But the case was complicated by the fact that Stewart had once been a stockbroker. The SEC contended that she should have known better.

9: You're a hedge fund manager, buying and selling stocks constantly. You pay a series of experts to feed you hush-hush information about pending mergers, and you earn millions in profits by buying shares of takeover targets before deals are announced. Insider trading?

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is B. B. Definitely insider trading

If you bribed or bought insider information and traded on it, you're going to prison.

10: You're a hedge fund manager, and you pay dozens of analysts and consultants to provide seasoned advice about stocks to buy and sell. Some of those consultants may have access to secret information, but you trade based on a wide array of factors, including examination of public documents and detailed analysis about industries and companies operating within them. Insider trading?

  1. A. Not insider trading
  2. B. Definitely insider trading
  3. C. Will draw SEC scrutiny, but maybe not a prison term

The correct answer is C. C. Will draw SEC scrutiny, but maybe not a prison term

This situation probably is not insider trading. The key to the famous 2009 case against Galleon Group CEO Raj Rajaratnam, says Stoltmann, hinged on whether his lawyers were able to establish that his trading was based on assembling a "mosaic" of information or whether he paid "consulants" to feed him insider tips. The former, says Stoltmann, is perfectly legal. Unfortunately for Rajaratnam, on May 11, 2011, he was found guilty of the latter -- specifically, nine counts of securities fraud and five of conspiracy to commit securities fraud.

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