Skycaps are having a hard time these days - the TSA isn't making their lives any easier and lots of folks assume that the $2 curb-side check-in fee goes in their pocket (it doesn't). As a result the skycaps in Miami have apparently become more and more pushy about getting the gratuity they believe they deserve-
I checked one bag with him, and, after giving him $2 plus $1 tip, he said my tip wasn't enough. I thought he was joking. He said $2 went to American Airlines, and he needed more than a dollar tip per bag to make a living. I said I thought the gratuity was up to my discretion. He said not if I wanted my bag intact when it arrived in Chicago - and suggested I take my bag inside if I didn't give him a better tip.
I was stunned and asked the skycap next to him if harassing customers for tips was part of American's policy. He said yes, with a smug look. I said I was going inside to talk to customer service. As I walked away with my baggage-claim number, he said he couldn't guarantee my bag would arrive safely in Chicago.
I boarded the plane and picked up my suitcase in Chicago without a problem. But, when I got home, I found bags of messy garbage in my luggage! I had to dry-clean some clothing and am considering throwing away the suitcase. (from the Daily Southtown)
So, if you're not willing to shell out $5 or more to make the skycap feel properly rewarded you're probably better off just taking your bags inside yourself.