On July 15, 2023, at 1515 eastern daylight time, a Piper PA46-500TP airplane, N444RR, was substantially damaged when it was involved in an accident near Vineyard Haven, Massachusetts. The pilot was fatally injured, and the passenger sustained minor injuries. The flight was operated as Title 14 Code of Federal Regulations Part 91 personal flight. According to the passenger, the pilot had just performed a go-around while on approach to runway 6 at Martha’s Vineyard Airport (MVY), Vineyard Haven, Massachusetts, when he experienced a medical emergency and “blacked out.” The passenger, who was not a pilot, took the flight controls and made an emergency, gear-up landing on airport property. The airplane bounced several times after touchdown, then came to rest upright with the left wing fractured. According to the passenger, there were “no mechanical issues whatsoever” that would have precluded normal operation of the airplane. According to FAA airman records, the pilot’s most recent third-class medical certificate was issued June 1, 2023. Previously, the pilot had been granted a third-class Authorization for Special Issuance medical certificate, which required that he provide extensive documentation of his health conditions to the FAA. A review of the pilot’s medical history revealed that he had high blood pressure since 1970, which he treated with medications, as well as coronary artery disease with prior heart attack, and coronary artery bypass graft (CABG) procedures in 1981 and 1996. He also had a history of atrial fibrillation since 2019, which he treated with blood-thinning medication to reduce the stroke risk posed by the condition. The pilot’s first aviation medical examination after either of his CABG procedures was in 2002. Between 2002 and 2005, there was no documentation that his heart disease was reported to or identified by the FAA. The first aviation medical examination at which the pilot reported a history of coronary artery disease and prior heart attack was in 2006. Between 2006 and 2022, the FAA granted the pilot a series of Authorizations for Special Issuance of third-class medical certification, based on annual medical testing and favorable status reports from the pilot's primary care and cardiology physicians. The pilot's most recent Authorization for Special Issuance was granted in July 2022. The Authorization letter did not authorize Aviation Medical Examiner (AME) issuance of medical certification at the next examination, due June 2023. Instead, the letter indicated that the FAA would decide about granting the pilot another Authorization of Special Issuance based on review of additional information that the pilot was required to submit in advance of that examination. The FAA had not yet received that information by the time the examination occurred on June 1, 2023, and had not granted any new Authorization for Special Issuance or completed any action to change the status of the pilot’s medical certificate at the time of the accident. At the pilot’s June 1, 2023, aviation medical examination, he reported a history of high blood pressure and atrial fibrillation. He reported using the medications apixaban, atorvastatin, chlorthalidone, doxazosin, eplerenone, and potassium chloride. Records from the examination did not include any indication that the pilot reported his history of coronary artery disease, heart attack, or CABG to the AME. There also was no indication that the pilot presented his Authorization of Special Issuance letter to the AME, as required. The AME, who had not previously evaluated the pilot, noted the pilot’s atrial fibrillation, documented that the pilot met Conditions AMEs Can Issue criteria for high blood pressure, and did not note any other cardiac history. The AME then issued the pilot a third-class medical certificate limited by a requirement to use corrective lenses to meet vision standards at all distances. On June 8, 2023, 7 days after the medical examination, the FAA received the medical documents that were needed to reevaluate the Authorization for Special Issuance for the pilot. These included a March 2023 laboratory report, a May 2023 echocardiogram report, a May 2023 treadmill stress echocardiogram report, and a May 2023 report of a 24-hour cardiac monitoring study. Additionally, the FAA received May 2023 letters from the pilot's primary care and cardiology physicians. Similar to previous such letters in the pilot's FAA medical certification files, these letters characterized the pilot as being in stable, outstanding health, with above-average exercise capacity, great compliance with medications and monitoring, and an excellent prognosis. Following the accident, first responders found that the pilot was in cardiac arrest upon extricating him from the airplane. He regained a pulse with resuscitative efforts and was transported to a community hospital before being transferred by air ambulance to another hospital, where he died five days after the accident. During his hospital stay, he did not have any sustained ventricular arrhythmia, nor did he have conclusive electrocardiographic or echocardiographic findings of a new heart attack, although biomarkers indicative of heart muscle damage were elevated following his cardiac arrest. The cause of his initial cardiac arrest was not definitively diagnosed but was documented as likely scar-mediated ventricular arrhythmia versus less-likely acute coronary syndrome. The Commonwealth of Massachusetts Office of the Chief Medical Examiner (OCME) performed an autopsy of the pilot. According to the autopsy report, his cause of death was hypertensive and atherosclerotic cardiovascular disease, and his manner of death was natural. His heart was enlarged, with thickening of the ventricular walls and interventricular septum. Coronary artery disease was also noted. The pilot’s toxicological testing after the accident included negative hospital tests for ethanol and tricyclic antidepressants using serum collected at 1809 on the date of the accident. Testing performed at the request of the OCME detected alprazolam at 3.1 ng/mL in serum/plasma collected at 2008 on the accident date. Testing performed by the FAA Forensic Sciences Laboratory detected alprazolam at 4 ng/mL, as well as atorvastatin, chlorthalidone, doxazosin, and tadalafil, in serum collected at 2220 on the accident date. Other medications detected by the pilot’s toxicological testing were documented in hospital records as having been administered to him after the accident, and before specimens were collected for investigative purposes.