pinniped

For those who put more of the blame on the family here: I'd agree, if the family was comprised of Flyertalkers. We know better. @:-)

Flyertalkers know you can easily get a gate pass, but the TSA and airline have been pretty effective at making the general public think this is nearly impossible.

Flyertalkers are generally aware of which airport personnel are airline employees, which are contractors to the airline, and which are contractors to the airport. However, skycaps in particular have a vested interest in acting very much as if they are a counter agent. The ones positioned at the Southwest curbside will appear, to many travelers, to be wholly in support of Southwest Airlines. If one tells an inexperienced traveler "I'll take your mom to the gate and make sure she gets onboard", most people wouldn't think twice about that.

When something goes wrong with that, it's natural to be angry at the airline. Even if the airline says "The Skycap works for a contractor", it doesn't really change anything. (I hate that cop-out myself: "Blame our contractor, our subsidiary, our franchisee, etc." I don't do business with contractors: I'm doing business with the main brand, in this case that's whatever is painted on the side of the fuselage.)

What's done is done and there's probably nothing else the family can do. Southwest gave them $200 in vouchers for an 11 hour delay, which is effectively them stating "This totally wasn't our fault." But I also don't know how far they'll get complaining to the airport authority or the Skycap contractor either.