Details of Disappearance
Winfrey was last seen on October 23, 2019. He and Kayla Rodriguez took off in his plane, a red and white single-engine Piper Arrow with the tail number N4958, from Novato, California at 6:22 p.m. A photo of the plane is posted with this case summary. They were headed north, for Mendocino County, California, but never arrived.
Per Verizon data usage records, Rodriguez attempted to access her phone at 9:14 and 9:15 p.m. Radar last tracked the plane five miles off the coast, between Rockport and Wheeler, California, at 9:23 p.m. Then it disappeared. A two-week search turned up no sign of Winfrey, Rodriguez or the plane.
Rodriguez was a labor and delivery nurse at California Pacific Medical Center at the time of her disappearance, and Winfrey was her landlord. He is a businessman and had just gotten certified as a mortician. Both lived in San Francisco, California, and that city's police are investigating their case. They are presumed dead but their bodies have never been found.