Tax Court Not Convinced That F. Lee Bailey Didn’t Have Fun Owning a Custom-made Yacht

For those of you not familiar, F. Lee Bailey was one of the defense lawyers on O.J. Simpson's dream team of attorneys. His star moment was when he asked the lead detective on the case, Mark Furhman, if he had used the n-word in the last ten years, who said that he had not. When evidence was produced to prove otherwise, well…that didn't do much for Furhman's credibility and Bailey was a hero (of sorts). Naturally, Furhman went on to be a commentator on Fox News, but I shouldn't digress.

For some of you older readers, you'll also remember that Mr. Bailey was also the defense attorney for Patty Hearst, the newspaper heiress, who committed bank robberies with her kidnappers, the Symbionese Liberation Army, using Stockholm Syndrome as a defense strategy. He also served as a defense attorney other notable trials in the 60s and 70s.

More recently, he's had some tax troubles and represented himself in U.S. Tax Court. He managed to win the main issue in the case, "a long story involving a foreign fugitive," but was less successful in other aspects of the case including hobby losses. You see, when you're a successful high-profile defense attorney, you will no doubt find yourself with some luxurious hobbies to pass the time. Like yachts! For you and me, yachts look hella-fun. Sun, water, people lounging on the deck. What's not to like? Well, Joe Kristan reports that FLB didn't like this yacht business. Not one bit:

He failed to convince the judge that his custom-built yacht was a “for-profit” activity.  One of the elements of the “hobby loss” tests is whether the taxpayer derives personal pleasure from the activity.  Mr. Bailey said the yacht was just no fun.  From the Tax Court opinion:
 
The Commissioner contends that Mr. Bailey took a great deal of personal pleasure from sailing on the Spellbound with his family and friends, but Mr. Bailey claims that “[i]t’s no fun to drive a boat”. Mr. Bailey testified that the steering wheel and navigational instruments of the Spellbound are isolated from the rest of the deck, and the pilot is therefore isolated from the party-goers on the deck.
 
While it may be true that Mr. Bailey did not enjoy piloting the yacht, the record belies the claim that he derived no personal pleasure from it. First, the Spellbound was built to Mr. Bailey’s specifications, and he testified that it was beautiful. Second, the record does not show that Mr. Bailey always took on the job of piloting the Spellbound. PBR hired a captain and crew to sail and maintain the Spellbound, and Mr. Bailey could have used their services to pilot the yacht any number of times. Even assuming arguendo that Mr. Bailey piloted the Spellbound on every personal trip–and that he disliked the task–we find that he derived pleasure from sharing the yacht with his family and friends and that he anticipated doing so when he purchased the yacht in 1989.
Apparently, despite all his years of lawyering and dealings, FLB neglected to learn a very important rule when it comes to boats. Next time!
 

Have something to add to this story? Give us a shout by email, Twitter, or text/call the tipline at 202-505-8885. As always, all tips are anonymous.

Related articles

What COVID-19 Tells Us About … SALT

COVID-19 may be the newest exacerbator of high blood pressure in humans, and it is having an effect on another well-known catalyst for stress, SALT. But this is not your old-fashioned table variety we are referring to. In the accounting department at the University of Maryland’s Robert H. Smith School of Business where I teach, […]