Simply Tax Episode 83

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2019 was yet another busy year in the tax world! Tony Nitti returns to the podcast to share key takeaways from his top tax cases of the year with host Damien Martin, along with advice for reading and staying current with tax case law. Here’s what’s covered in our final episode of 2019:

Background, tips and tricks on studying tax case law:

  • Why read tax cases? @01:56
  • Tony’s tips for reading tax case law @04:12
  • How to fit reading tax cases into the busy day-to-day @09:14
  • How Tony picked his top 10 cases @11:41

Top 10 tax cases:

  • Gaylor v. Mnuchin, 919 F.3d 420 (7th Cir. 2019) @14:41
    • What’s Internal Revenue Code (IRC) Section 107?
    • Why did the Freedom From Religion Foundation sue the IRS?
    • What are the key takeaways from this case?
  • Northern California Small Business Associates v. Commissioner, 153 T.C. 4 @34:44
    • What’s IRC §280E?
    • What was the taxpayer’s argument in this case?
    • Why did the court reject this argument?
  • Langston v. Commissioner, T.C. Memo 2019-19 @47:48
    • Why was there even an issue here?
    • What’s the significance of this case?
  • Barbara v. Commissioner, T.C. Memo 2019-50 @54:24
    • Why is material participation so important yet challenging?
    • Why did the tax court disagree with the IRS in this case?
    • What’s the key takeaway from this case?
  • Eger v. U.S., 124 AFTR 2d 2019-5717 @1:07:19
    • What’s IRC §469(c)(7)?
    • What did we learn from this case?
    • Three things to remember about real estate professionals
  • Donoghue v. Commissioner, T.C. Memo 2019-71 @1:24:30
    • Is this just another bad-facts case about horses?
    • What are the hobby-loss rules and why are they so tricky?
    • What’s the key takeaway from this case?
  • Ames D. Ray v. Commissioner, T.C. Memo 2019-36 @1:37:00
    • Why have we been talking so much about IRC §§162 and 212 lately?
    • Why did the taxpayer feel he could deduct his legal fees?
    • Why did the court ultimately disagree?
  • Lipnick v. Commissioner, 153 T.C. 1 @1:45:57
    • What are the debt-financed distribution interest expense rules?
    • What was the issue of first impression here and how did the court rule?
    • What’s the key takeaway from this case?
  • Mihelick v. U.S., 927 F.3d 1138 (11th Cir. 2019) @1:52:41
    • What’s the claim-of-right doctrine? 
    • What did we learn about this doctrine from this fact pattern?
  • Brown v. Commissioner, T.C. Memo 2019-30 @2:03:22
    • Why does it matter where your tax home is?
    • What are the factors to determine where a taxpayer’s regular and principal places of business are?
    • What’s the key takeaway from this case?

Bringing it all together:

  • Shrinking the code @2:10:28


Tony Nitti is a tax partner at RubinBrown. His practice focuses primarily on corporate and partnership tax planning, with a special focus on the consolidated return regulations and the reorganization provisions, including the structuring of acquisitions, mergers, reorganizations, spin-offs and other restructuring transactions. Tony is a contributor to Forbes and his opinions and commentary on important tax issues have been quoted in Bloomberg, CNN Money and the BNA Daily Tax Report.

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