Kennedy was no raving conservative by any means but he did do a few things liberals today would oppose such as his meddling in Vietnam (the Diem episode especially) and his tax cuts to spur the economy. Regarding the Cuban Missile Crisis, people see that as some great Kennedy victory but the fact remained that Khruschev had no choice whatever other than to pack up and leave. The US had at least 10-1 nuclear superiority at the time, perhaps much higher. There was zero chance of the Russians firing any missiles over Cuba. What Khruschev did get, though, was the removal of our missiles in Turkey, something we needn't have offered under the circumstances. So, the CMC was really a net gain for the Russians.