There's never that problem on Southwest airlines because of their two bags fly free policy. I've had my carry-on checked by a flight attendant a few time too. I don't know how I would have excepted them checking an expensive leather carry-on...it's bad enough worrying about the contents. Another problem is everyone standing up at the same time trying to pull out their stuffed bags. It's even worse when you have connecting flights. They could easily curve the problem by allowing one free checked bag and charging more for the second.