Pin flat on the end? Since the connector is already written off I'm thinking preheat everything a bit with air and then drive all the heat you can into the pin alone with the 888 and a heavy tip with with a suitable flat on it, crank the tip temp to get as much stored energy as possible. It'll hopefully heat up enough to melt all the solder eventually (5-10 seconds?), which can then be sucked or blown out.
Can you expand on the 301 tip trouble? Kind of goes without saying, but if you can't get on the pin/pad good with clearance for solder to flow through, that'd probably be your problem.