Sounds like
the Murray case, in which the pilot had done work for the bar owner in the past, which made it reasonable to think that he might be hoping that the favor would enhance his chances of doing so again in the future. Excerpt:
There is no evidence that respondent received any money
directly. (Mr. Fitzgerald was subpoenaed by the Administrator to
testify but failed to appear.) Nevertheless, compensation need
not be direct nor in the form of money. Goodwill is a form of
prohibited compensation. Administrator v. Blackburn, 4 NTSB 409
(1982).
The evidence establishes that, not only was respondent a
friend of Mr. Fitzgerald, but he had done work for him in the
past. Interpreting the facts in a way most favorable to
respondent and assuming that he really had no expectation of any
kind of benefit, strains credulity. Respondent testified that
these flights cost him about $1100. The law judge, who had the
opportunity to witness respondent’s demeanor, judged his
credibility and rejected his Good Samaritan argument. The law
judge was unable to accept respondent’s claim that he would
freely transport people he did not know at a personal expense of
over $1000 simply for pleasure. We have no basis to overturn
that decision.
One thing I don't see mentioned in the case is that the wording of the regulation actually made it unnecessary to determine whether the pilot received compensation:
§61.113 Private pilot privileges and limitations: Pilot in command.
(a) Except as provided in paragraphs (b) through (h) of this section, no person who holds a private pilot certificate may act as pilot in command of an aircraft that is carrying passengers or property for compensation or hire; nor may that person, for compensation or hire, act as pilot in command of an aircraft.
Note that there are actually TWO things prohibited by that paragraph, the part before the semicolon,
...no person who holds a private pilot certificate may act as pilot in command of an aircraft that is carrying passengers or property for compensation or hire;
and the part after the semicolon,
nor may that person, for compensation or hire, act as pilot in command of an aircraft.
The second part prohibits the flight if the pilot is receiving compensation for it. The first part prohibits the flight if ANYONE is receiving compensation for it, even if the pilot himself receives nothing. And in the description of the facts of the case, it was mentioned that the passengers paid for the flight as part of a package deal:
Mr. Ed’s charged a flat price for the party, and it included air transportation.
