Quayle should have said to Bentson in the 88 debate: Actually you DIDNT know Kennedy. He was a tax-cutter. You are a tax-raiser.
A few weeks after that moment, I remember reading a story that had a quote from Dave Powers, one of JFK's closest aides, who was at the time the director of the Kennedy library. Powers said that they had searched and searched through their files and could find no photo of Bentsen and JFK, or any direct knowledge that they were friends.
Bentsen did serve in the House in the early '50s when JFK was also a congressmen, and likely Bentsen did know him well enough to say hello, but they were hardly the friends he said they were.
Of course, this story did not get any national traction at all. And Quayle did put his foot in it by saying earlier that he was just as experienced as JFK, etc.