NAFA member David G. Mayer, partner at Shackelford, McKinley & Norton, LLP, shares his latest blog.
Trust the real experts, not armchair ‘experts,’ when buying an aircraft.
As I considered topics for my milestone 50th blog in AIN, I decided to share stories behind real jet purchases showing how clients have made avoidable mistakes in their aircraft selections, regulatory structuring and implementation, and/or tax planning. Their errors cost them millions of dollars, disrupted their travel, or entangled them with the FAA. As I have said before: Do not embark on the journey to purchase an aircraft without a qualified aviation team supporting you.
A client wanted to buy a jet quickly (aircraft 1) so he could go on a fishing trip with his friends. In rushing to close the deal, the client sacrificed most of the standard aircraft due diligence. Within a few months, the client returned with a plan to buy a different aircraft (aircraft 2) because aircraft 1 apparently did not meet his needs. He eventually sold aircraft 1 at a loss of hundreds of thousands of dollars.
Astonishingly, a few months later, he returned again with a new plan to buy a different aircraft (aircraft 3), as aircraft 2 apparently did not work for him either. He eventually sold aircraft 2 at a significant loss. The third time was the charm, but at a high cost in money and time.
Perhaps an even worse scenario, early in the pandemic aircraft-buying frenzy, a technology CEO bought a large-cabin business jet for cash at an elevated price. Realizing the error of his ways, the CEO never flew the aircraft, though he owned it for a year and then needed to sell it.
Compounding this problem, he also needed to “refinance” the aircraft (extract its equity) to fund his nascent business. For at least six months after closing the loan, he paid a high interest rate on top of transaction costs and loan fees. When he sold the aircraft, he lost nearly $2 million, including $600,000 for undiscovered repairs found during a later pre-buy inspection and expenses to unwind the financing.
This article was originally published on Aviation International News (AIN) on March 13, 2026.