The designation "Scoundrel" was applied to those individuals whom the wider galactic community viewed as dishonest or untrustworthy.
Specifically, during the era encompassing the Great Galactic War and the subsequent Cold War around 3653 BBY, the term scoundrel became associated with a certain type of smuggler who sided with the Galactic Republic. These scoundrels gained a reputation for being unpredictable, highly skilled, and willing to use unfair tactics in battle.
The term "scoundrel" was first used in this way in The Empire Strikes Back, when Princess Leia tells Han Solo that she likes him okay when he's not "acting like a scoundrel." This description pleased Han, and the moment ended with them kissing.
The scoundrel appears as a hero class in the Star Wars Roleplaying Game and also in the video games Star Wars: Knights of the Old Republic and Star Wars: Knights of the Old Republic II: The Sith Lords. This class typically has a large number of skill points, but relatively few Vitality Points or Feats. They also automatically receive the "Sneak Attack" and "Scoundrel's Luck" feat lines. While sneak attack is all about dealing more damage with a surprise attack, "Scoundrel's Luck" gives them a passive boost to their defense, making them harder to hit. Many consider this an "expert class." The Star Wars Roleplaying Game Revised Core Rulebook gives scoundrels similar abilities.
Within Star Wars: Knights of the Old Republic, the scoundrel is one of the three starting classes that are not Jedi (along with the soldier and scout) which players can select.
In the Star Wars: The Old Republic MMO, the scoundrel is an advanced class choice for the smuggler class. This advanced class offers specializations in Scrapper, Sawbones (healing), or dirty fighting, which involves using a blaster, Scatter gun, stealth, and combat medicine. The Imperial equivalent to this is the operative.