It could happen to someone who wasn't prepared with multiple ways of determining his position during the flight (pilotage, ded reckoning, VOR cross checks and GPS). Perhaps he was relying solely on one method, and hadn't planned for any of the others when the sole method failed him (handheld GPS running out of batteries, for example).
Perhaps he thought he was approaching FRG, turned inland, couldn't spot the airport, then did some 360's while he worked it out.
The sad truth is that, in absence of a sudden medical issue, it should've been easy to avoid this problem with some really basic planning prior to the flight. That he should've been more prepared to fly through some of the most complex airspace in the country.
A plan as simple as, "if the GPS craps out, stay along the shoreline at 400ft until passing the first bridge approaching the Jones Beach Monument, then climb to 3500. At the monument, turn left to hdg 040, climb to a higher altitude (below 4000) and look for FRG dead ahead. " If equipped with VOR, he could stay on the shoreline until hitting the DPK R-221 then head to DPK, looking for FRG off the left.
This plan took about 5-7 seconds to formulate by looking at the TAC, and would've worked in good weather regardless of the nav equipment on board.
It would be very interesting to find out what caused him to get lost, and his thought process once he was lost (if that's what happened). At the VERY least, once he was lost, why he would not contact ATC is beyond me. A quick look at the chart shows that if you were heading to FRG, and got lost, JFK could easily become a factor, and on that basis alone, he should've wasted no time and called SOMEONE for help. If nothing else, that's what I learned from thinking through this.
