in theory you could earn probably a million miles if you fly to every destination.
like I flew to ALL of JetBlue's island destinations
+10000 Trueblue points
I flew to 13 of JetBlue's island destinations
+5000 Trueblue points
I flew to 6 of JetBlue's island destinations
+500 Trueblue points
thats 15,500 miles besides for these. The thing is, I think you earn badges on mileage flights. So in theroy you could probably pull this off with say 200k starting miles, fly to every destination and earn 500k