Introduction
The Zhentarim Ruffian feat is all about creating and capitalizing upon opportunities. Family First will help your whole party act early in combat, and Exploit Opening can make your Opportunity Attacks extra lethal.
Rogues may find Zhentarim Ruffian particularly useful, allowing them to improve the damage on Opportunity Attacks which can apply Sneak Attack, as well as making it easier to deal Sneak Attack in the first round of combat.
Zhentarim Ruffian is required for Zhentarim Tactics.
Exploit Opening
If your character makes a lot of Opportunity Attacks, rerolling the damage and choosing the higher value can protect you against poor rolls. This will become much more impactful if you also take Zhentarim Tactics, which allows you to make an Opportunity Attack if you’re hit with an attack by a creature within 5 feet of you.
This combines very nicely with Sentinel, which provides an easy way to trigger Opportunity Attacks by letting your allies get hit.
Exploit Opening notably doesn’t specify that you reroll weapon damage, just “damage,” so it appears that you can reroll spell damage if you use War Caster to cast a spell in place of an Opportunity Attack. That’s a good excuse to hit your target with a big damage spell.
It’s unclear how this interacts with Savage Attacker. Talk to your DM and come to an agreement if you end up with both feats. My suggestion: roll the full damage dice twice, then choose the higher. Then roll just the weapon damage dice (Savage Attacker only affects the weapon damage dice), compare them to the previously-chosen weapon damage dice, and choose the higher of the two.
Family First
Simple, effective, and the entire party benefits. Look for an easy source of Heroic Inspiration, such as playing a Human or a party member with the Musician Feat.
