There is no dispute that this expression is used to describe a cheap or misery person. However, we have choices for the origin. World Wide Words says the word “skate” was used to express contempt, and it evolved into “cheapskate” in the late nineteenth century. The term was originally used to describe a worn-out horse, a mean or contemptible person, or a second-rate sportsman. Wiki answers has two other possible explanations for the origin, and both are more colorful. One is that skates that strapped onto your shoes were so cheap that they often fell off, and were literally cheap skates. The other is that in the early 1900’s there was a panhandler named Kate Robinson who inherited a fortune, but continued to beg. Thrifty people were told “you are as cheap as Kate,” which when said quickly becomes “cheapskate.” My vote is that the last explanation is the most interesting.