At present, I am in Maine and CD is near London. In about 5 hours he flies from Heathrow to Dublin. Then he catches a plane from Dublin to Boston, with a stopover in Shannon. We are scheduled to arrive in Boston at about the same time, though I will be arriving with the kids in our rental car. The plan is to meet at the gate for our flight to Pittsburgh, since he has to claim a bag, clear customs, and re-check his bag when he gets to Boston.
There are so many things that could go wrong, I can't even run through the possibilities without risking total brain implosion.
I do know this, though. If I get to Pittsburgh without CD I'm going to have a hell of a time finding the car in the vast wasteland that is long term parking.