I scored one of the cheap transcon AA Economy Web Special deals to fly DCA -> PHL -> SFO in January, which is great except for one thing: the 33m connection time in PHL. I'm worried that even if my plane lands on time, I'll never make the connection after waiting for other pax to deplane (I'm booked into the first row outside of First Class) and possibly waiting for my gate-checked bag to return (I doubt my suitcase will fit in the overheads, and I'd prefer not to check my bag in case I miss my connection...). I'm on American's last flight to SFO out of PHL, so if I miss it I'm stuck there for the night. I'm thinking about getting the Freebird travel insurance for the trip, though not sure if that would even be helpful if there's no other flights PHL -> SFO.

Any thoughts on whether this connection is viable? And if it isn't, are there any alternatives/contingency plans I should look into?