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Bitcoin The Almighty Buck The Courts

Bitcoin Makes Historic First Appearance In US Supreme Court Opinion (ccn.com) 29

hyperclocker shares a report from CCN: Thursday marked a historic day for bitcoin, as the flagship cryptocurrency made its first appearance in an opinion published by the U.S. Supreme Court. The case, Wisconsin Central Ltd. v. United States, did not involve bitcoin's regulatory or legal status. Rather, it examined whether employee stock options represent taxable compensation under the Railroad Retirement Tax Act of 1937.

That may seem like an unlikely place for a discussion of bitcoin to appear, however, as justices noted in both the majority and dissenting opinions, the case forced them to consider a fundamental question that has also taken on a renewed importance in the decade following the publication of the Bitcoin white paper: "What is money?"
"Ultimately, the 5-4 majority ruled that employees should not be taxed for exercising stock options since the action does not constitute 'money remuneration,'" the report adds. "However, writing in a dissenting opinion, Justice Stephen Breyer argued for a 'broader understanding of money' and said that stock options should be classified as taxable compensation."
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Bitcoin Makes Historic First Appearance In US Supreme Court Opinion

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  • It's a bit confusing, but rest assured, corporate CEOs, that there are ways around paying income tax [investopedia.com] as long as the wording and protocol are just right.

    Non-qualified stock options differ from incentive stock options in two ways. First, NSOs are offered to non-executive employees and outside directors or consultants. By contrast, ISOs are strictly reserved for employees (more specifically, executives) of the company. Secondly, nonqualified options do not receive special federal tax treatment, while incentive stock options are given favorable tax treatment because they meet specific statutory rules described by the Internal Revenue Code...

    • Re:Hmmm (Score:5, Insightful)

      by Anonymous Coward on Thursday June 21, 2018 @04:56PM (#56825104)

      Maybe for CEOs. But for the rest of us, if you've ever been caught in the exercised non-qualified stock option trap, you'll know why they should not be called compensation. Basically the IRS expects you pay taxes even if the value has dropped below the exercise price and you sold in order to stop losses during the qualification period. You can write off the losses later, but only against a few thousand of regular income each year. Pay up now, we'll "give" you the loss later.

      • Re: (Score:2, Interesting)

        No idea why your comment was modded down as you are exactly right. Back in the 90s, hundreds of Sun Microsystems were caught by this trap in which they exercised stock at their low "purchase price" of say $10/share while its fair market value was an order of magnitude greater. The taxes they owed on pieces of paper became the fair market price at time of exercise minus exercise price * number of shares. Then quite suddenly the stock crashed, the IRS came for their taxes the following April, and people wh
        • Re: (Score:2, Informative)

          by Anonymous Coward
          That was not the IRS's fault, that was the fault of the morons that on exercising kept the shares. Everyone with half a brain during that period exercised and sold the shares in a single transaction, I had my share of options back then and also watch many people get burnt like you explained, but that was purely their own fault and a decision they made.
        • Re: (Score:2, Informative)

          by Anonymous Coward
          you are blaming the IRS for a greed based risk that people chose to take. maybe they were poorly informed or just stupid, but this was not some random screwing by the IRS, it was a financial risk/investment they took on themselves and lost. The IRS doesn't get to make decisions for your investment stupidity, nor do they or should they compensate you for your stupidity.
        • Tax is applied the moment you receive a benefit/payment from your employer. At that point you get to make a decision, Do I take a risk and keep the asset even though I have just incurred a tax debt or do you dispose of the asset and collect your money. those that got burnt chose poorly, though many people also hugely profited from that risk exposure. Personally I always vested my options and disposed of the shares in a single hit, no risk and take the cash. I can then if I choose repurchase the shares or mo
        • Re:Hmmm (Score:4, Insightful)

          by Kjella ( 173770 ) on Thursday June 21, 2018 @06:08PM (#56825452) Homepage

          Back in the 90s, hundreds of Sun Microsystems were caught by this trap in which they exercised stock at their low "purchase price" of say $10/share while its fair market value was an order of magnitude greater. The taxes they owed on pieces of paper became the fair market price at time of exercise minus exercise price * number of shares. Then quite suddenly the stock crashed, the IRS came for their taxes the following April, and people who had briefly been theoretical millionaires were instead taxed like millionaires but in fact held nothing of value.

          1) If you know the tax bill is coming at least sell enough to pay it off while you're still a "theoretical millionaire" even if you want to speculate on the rest.
          2) They could have bailed out any time in the same year and have an equally big deductible loss.

          I'll admit that once you put yourself in that hole though you got a problem. The IRS will want money on your imaginary profit and you can't effectively use your unrealized loss to cover it.

  • had lots of AOL friends who had stock stolen from them in the 90s when the Time Warner buyout happened. A judge just gave them the middle finger. If the stock has monetary value you pay taxes on it. Hell, if I trade chickens for corn that gets taxed. Why not this?
  • I exercised some options on pre-IPO (i.e., completely non-tradable) stock back in 2011 because I was planning to leave the company and thought it might IPO.

    Alas, it did not, but the IRS considered the difference between my option price and some theoretical measure of what the CEO claimed the stock would be worth then if it were tradable to be income. Which pushed me into AMT Hell.

    The company still hasn't IPOed, and its remnants seem to be circling the drain, more or less, as near as I can tell.

    I'd sure li

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