The scenario described—a commercially rated pilot hired separately by a lawyer who has independently leased a Piper Saratoga to transport herself and colleagues to a court case—sits squarely in one of the most persistently confusing corners of FAA regulation: the line between Part 91 operations and Part 135 commercial carriage. The core question is whether the arrangement constitutes "common carriage" requiring a Part 135 certificate, or whether it can legally proceed under Part 91 with a separately hired pilot. The structure described (lessee leases the aircraft, then separately hires a pilot) is a classic pattern the FAA and courts have scrutinized for decades, most notably through the "wet lease" versus "dry lease plus separate pilot services" distinction. If the lessor of the aircraft (or an affiliated entity) is the one arranging for the pilot, or if the arrangement is structured to functionally recreate an air taxi service while dodging Part 135 certification, the FAA has consistently found this to be illegal "flying club" or sham dry-lease arrangements—regardless of how the paperwork is styled.
The mention of an NBAA exemption under Subpart F (14 CFR 91.501) is a red herring in this context, and understanding why matters for working pilots asked to fly under similar informal arrangements. Subpart F provides limited relief for large aircraft and turbojets (generally over 12,500 lbs or multi-engine turbojets) operated by companies transporting their own employees and guests in furtherance of the company's business, without common carriage compensation flowing directly for the flight itself. A Piper Saratoga, a single-engine piston aircraft well under the weight threshold, does not qualify for Subpart F treatment at all—that provision is irrelevant here regardless of how business-related the trip is. The more applicable analysis is whether this constitutes common carriage under Part 135, evaluated through the FAA's four-part test from cases like the classic "Rogers v. FAA" line of interpretations: holding out to the public, transportation from place to place, for compensation, and an implied contract or agreement. If the lawyer engaging the pilot's services is doing so as a one-off private arrangement for her own transportation needs (not holding herself out to the public, not running a transportation business), and the pilot is being compensated for piloting services only—not for use of the aircraft—many interpretations would treat this as permissible under Part 91, similar to how an owner might hire a contract pilot to fly their own aircraft. However, the moment money changes hands in a way that could be construed as payment for carriage of passengers (rather than strictly for pilot services), or if the arrangement starts to look like the pilot or an intermediary is effectively selling transportation, FAA enforcement and case law (including the long history of "time-share," "interchange," and illegal charter enforcement actions) become directly relevant.
For working pilots, particularly commercial certificate holders who take on freelance or contract flying gigs, this type of question underscores why so many enforcement actions and legal opinions revolve around compensation structure and holding-out rather than aircraft ownership or lease status alone. The FAA's Office of Chief Counsel has issued numerous interpretations over the years (the Mangiamele, Wilson, and Zecca letters among them) addressing exactly this fact pattern: a passenger leases an aircraft and separately hires a pilot, and whether that constitutes illegal charter depends heavily on who initiated the flight, who controls operational decisions, and whether the pilot or a broker is effectively packaging the trip as a transportation service. Pilots should be wary of any lease-plus-separate-pilot arrangement that was set up by the same party (broker, FBO, or flight department) for the specific purpose of moving passengers, since the FAA has repeatedly found such arrangements to be de facto Part 135 operations dressed up as Part 91 dry leases—exposing both the pilot and the aircraft operator to certificate action and civil penalties.
This question also reflects a broader and ongoing tension in general aviation and business aviation between the flexibility owners and renters want under Part 91 and the safety oversight the FAA insists on for compensated passenger-carrying operations. It parallels debates seen in fractional ownership, aircraft leaseback arrangements at flight schools, and the rise of app-based flight-sharing platforms (several of which the FAA shut down for constituting illegal common carriage). Any pilot approached with a similar "lease the plane separately, hire me separately" proposition should treat it as a serious legal gray area, consult the FAA's published legal interpretations or an aviation attorney before accepting the job, and recognize that verbal reassurances about "it's just a dry lease" do not shield either the pilot or the aircraft owner from enforcement if the underlying substance of the transaction reveals compensated passenger transport dressed up to avoid Part 135 certification requirements.