The Sleepiest Tax Lawyer

Being a tax lawyer can be quite creatively inspiring. For example, when I was working as a tax lawyer in New York City a number of years ago I wrote a (still unpublished, for some reason) children’s book. The text follows.

The Sleepiest Tax Lawyer in New York City

Once upon a time there was a very sleepy tax lawyer. She could not stay awake. She slept on her desk, under her desk, and next to her desk. One day she decided to find out if there was any tax lawyer in the city who was as sleepy as she was.

First she went to Cravath. She met a very tall tax lawyer.

“Are you a sleepy tax lawyer?” she asked the Cravath lawyer.

“If a U.S. shareholder acquires, directly or indirectly, stock of a foreign or domestic corporation, which, by reason of the acquisition, then becomes a related controlled foreign corporation or a member of the affiliated group, then in determining excess related group indebtedness or excess U.S. shareholder indebtedness, the indebtedness and assets of the acquired corporation shall be taken into account only at the end of the acquisition year and in following years,” the Cravath lawyer said.

The Cravath lawyer didn’t seem very sleepy, although he had made the sleepy tax lawyer feel even sleepier. So she took a nap. When she woke up, she went to midtown to visit Skadden. At Skadden she met a very fat tax lawyer.

“Are you a sleepy tax lawyer?” she asked the Skadden lawyer.

“In applying section 108(e)(8) to any case to which subparagraph (A) applies, there shall not be taken into account any indebtedness for interest described in subparagraph (C),” the Skadden lawyer said.

“You don’t sound very sleepy either,” said the sleepy tax lawyer. She took a short nap and then went to visit Sullivan and Cromwell, where she met a very bald tax lawyer.

“Are you a sleepy tax lawyer?” she asked the Sullivan and Cromwell lawyer.

“Any ownership interest that otherwise would be treated as stock under paragraph (f)(18)(i) of this section shall not be treated as stock if treating the interest as not stock would result in an ownership change,” said the Sullivan and Cromwell lawyer.

“You don’t sound sleepy at all,” said the sleepy tax lawyer. “I must be the sleepiest tax lawyer in New York City! I’d better go back to my office and take a nap.” And so she did.

The End

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6 Responses

  1. Sam B. says:


    The only reason I can think that it hasn’t been published yet would be the illustrations. I know my 2-year-old daughter would eat it up, and doubly so if it had flaps for her to lift.

    The other day I was marking up a document at home, and she wanted to help me color the paper. She’ll probably follow me into the world of tax law, unless, of course, my wife has anything to say about it.

  2. That book is so porific. Thanks.

  3. Abe Carnow says:

    Where is the happy ending?

    And is there an implied statement here, that Rip Van Winkle actually grew up to be the Commissioner of the IRS?

  4. It’s not really a children’s book unless someone kisses her, wakes her up and rescues her from having to work all day. Perhaps the managing partner, who is captivated by her classic beauty and overheard her singing one day. Perhaps she sings in her sleep. And I agree about the flaps.

  5. Apep says:

    I volunteer to write the sequel about the formerly sleepy tax lawyer and modafinil.

  6. ART Bradham says:

    My college age daughter, also named Sarah, pronounces your story “wonderful. It knocked me right out.” She had relied on me for years to tell her tax stories; now maybe we have a new source. Flaps and coloring pages are required, for all ages.