About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. I never said anything about the tax rates, just that the IRS considers the miles bonuses income, just like other forms of income they tax. And I do believe that the IRS statement about “financial accounts” left things wide open to a broader enforcement. I’m not certain it is coming, but there certainly is much greater potential there now than previously based on the clarifying statement offered.

    As for poking the bear, I definitely agree that wasn’t a smart move.

  2. So lemme see if I understand this right. The IRS wants to tax me on something I don’t own under the terms and conditions of most frequent flyer programs. So what next? Will they tax me on the yacht I don’t own, too? If so, they can just take it out of the million bucks I don’t own.

  3. What is wrong with people? There is plenty of emperical data shows that you can effectively declare that value of miles on a 1099 for as little as you like, including 0$, and the IRS won’t even blink. Poking and prodding them is a horrible idea.

  4. A couple days ago I read an article that two universities created a genetically engineered highly contagious mammal-adapted variety of the avian flu so they could study it on ferrets, and I thought that sounded like a really terrible idea, but writing and asking the IRS to consider a public comment on taxing frequent flyer is probably an equally dangerous idea.

  5. The bottom line is that I think Citi is being evil issuing 1099s for the miles issued to checking account holders. I bet they must be taking a deduction as a marketing/business expense on their tax return too, otherwise they wouldn’t be so proactive in sending out those 1099s.

  6. ABC News- Channel 7 in NYC is airing a story about possibly being taxed on airline miles on the 11:00 news. Wish I knew earlier to let you know.

  7. Yes, it’s always best to keep a low profile with the IRS….this is NOT the type of attention that will help us.

    If you get a 1099 for an excessive amount, it’s best to report the full amount from the 1099 on your tax return, then take an offsetting deduction on a separate line (labelled something like “FMV adjustment) to bring the value down to what is fair. If you don’t do that, the IRS is likely to send you an audit letter (since they always match 1099’s to tax returns).

  8. It has always been my assumption, as a frequent flyer and tax professional, that the IRS will not pursue taxation of miles because they are a major perk for almost every politician, especially those in the Congress that live anywhere but Washington, D.C. I am surprised this has not been mentioned earlier…

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