Career Guide to Insider Trading, Chapter 18: To Rat or Not T

In previous chapters we covered important insider trading career questions such as Do I plead guilty or not guilty when the feds have me by the family jewels? and Do I use a pair of pliers and four garbage trucks when trying to get rid of incriminating evidence, or do I simply burn all of my USB drives in a 40-gallon barrel?

Now we turn to perhaps an even more important (and difficult) dilemma: When I get caught with my hand inside the insider trading cookie jar, do I make a deal with the feds and rat out the dude who stood directly behind me as I swore to the Absolute to respect and honor and be faithful to the love of my life until death to us part, or do I keep my mouth shut and protect my best man?

Indeed, it's a tricky question. And one that 35-year-old Harvard graduate Noah Freeman recently faced when caught insider trading by the feds.

Freeman -- who speed skated with, vacationed with, formerly worked at SAC Capital with, and apparently insider traded with his good buddy Donald Longueuil -- was presented with the opportunity by federal prosecutors to receive lenience by wearing a wire and getting Longueuil to continually incriminate himself on tape, or else take the insider trading rap that he had coming to him and protect his supposed closest friend.

Freeman ultimately chose the former (to rat), and it's not difficult to see why, given that lenience, in this case, did not mean something silly like Freeman would go free, get less jail time or receive a reduced fine, but in fact something much, much bigger -- that is, that he could "travel in coming months to Puerto Rico and the U.S. Virgin Islands, where he plans to attend triathlons with his wife, including the same race in St. Croix where [he] proposed marriage three years ago."

While it may be easy to say to yourself, 'Freeman had no choice, that's some seriously tasty piece of cheese the feds dangled in front of Noah,' I urge you to deeply reflect on the above situation and ponder what you really would have done if in Freeman's shoes. Remember, we're talking about watching your wife, and not just anyone, swim, bike and run.

In addition, here are three further questions for self-study: (1) If you're Freeman, do you still send holiday cards to Longueil? (2) If you're Freeman, do you fly first class or coach to Puerto Rico? and (3) If you're Freeman, in St. Croix, do you paint triple-digit numbers on your thighs, chest and biceps, illegally join the triathlon and, during the swimming portion of the race, attempt to escape federal surveillance by swimming to St. John?

(WSJ)

(Related: Career Guide to Insider Trading, Chapter 17: Evidence Shredding)