Sure, but tax breaks themselves are often fixed. Buying stock options is a great example of where you might end up with a fixed tax break. Buy 1000 options at

Sure, but tax breaks themselves are often fixed. Buying stock options is a great example of where you might end up with a fixed tax break. Buy 1000 options at your strike price ex: $1, pay tax on their current estimated value (say the value is estimated at $100, you pay tax on (100 - 1) * 1000 = $99,000 of "value" that you gained, probably about 20k). 2 years later: Boom, company goes out of business. That stock valued at 99k was actually worth 0k, but you paid taxes on 99k. So now you can write off approximately $3,500 (for this case) in taxes every year until you've written off that 20k you paid in taxes - about 6 years in this case. Has absolutely zilch to do with how much your P&L are. Those will still influence your final tax bill, of course, but they don't touch the break. --- Now - this case is not "avoidance" since you've paid the tax and are getting it back, but there are a lot of similar breaks related to loans, and the interest you're paying on loans - especially if the thing you're using that loan for is also taxed. So it's VERY possible that Uber has generated a $1 billion tax break every year through loan shenanigans. That doesn't mean that they won't pay taxes, it just means the yearly bill will be 1 billion lower than it probably ought to have been.