I'm late, but if anyone cares, here's your portuguese trivia for the night.
Malandragem is a word that is rooted on the term "malandro", which usually refers to an individual who's lazy and/or cunning.
To present an example, Tom Sawyer is a character who would fit the label.
Therefore, if you want a rough "1 by 1" translation of malandragem: slyness, shrewdness or "streetwiseness" would be close approximations.