Please excuse me for being a newb. Hopefully I have posted this question in the right place.

I just bought a SamsoniteŽ Black Silhouette 11 22" Upright Expandable Spinner and will be traveling SAN-JFK (757) in F and JFK-MXP (767) in J, both on AA of course.

It sounds like 22" bags are a roll of the dice. If I get through security in SAN, but board the aircraft and the FA's say the bag is too big, will they send the bag below and have be pick it up on the jet bridge at JFK, or will they try to check it all the way through to MXP? I'm also concerned about the same thing JFK-MXP. If they make me check while trying to board at JFK, will the bag be brought up as we exit the jet bridge or will it come out at baggage claim?

Would you recommend just checking and not worrying about the hassle. Or is it worth giving it a go and trying to get it on board?

Any suggestions/recommendation would be much appreciated.