Even though he is a criminal he seems to have good taste ,about his cigars, he says
THESE ARE SPECIALLY
MADE FOR ME BY A
LITTLE MAN IN TAMPA.
later he asks barney to buy him some cigars
why would someone that has handmade cigars want some cheap dimestore cigars??

There's a logical answer to that question, it was a test to gauge his ability to manipulate Barney. He got his answer and of course we know what happened next.

A sidebar to this discussion, Dan Tobin, the actor who played Caldwell was a regular on the final season of Perry Mason. He played a restaurateur added to the show mostly for comic relief. The shows ratings had been dropping since season 6, I can't understand why anyone would think adding Tobin would help turn the downward trend around.