I lived in Bermuda for most of the 1980s and early 90s. All the flights were tourist timings except Panam who had 1900 dep from JFK which night stopped and was an 0730 back. Rumoured that this was because the then Pan Am CEO had a house in ..... guess where.and could catch the Friday flight down and the Monday one back.
Bermuda had the US preclearance arrangements so you in fact entered USA at Kindley Field Airport and just walked through JFK as though it was dometic.
I had to make a day trip one day and I turned up at the airport to find I have lift my passport at home . Panic but remember that the senior Bermuda police officer on duty is often someone I know. I tracked him down and explained the situation. He went to see his US Immigration service opposite number . This guy hand wrote a letter to the duty officer at JFK saying I was a solid citizen that he would vouch for and in fact had played Golf with . Get to Kennedy and show them the letter- lot of hmm hmm and one calls his supervisor. He comes down to 'the border' gives me a handshake and says Welcome to the United states. -writes something on the letter and puts his official stamp on it , thats for the trip home tonite.
Much as people in organisations do know each other I cant see that happening very often today