Thug
Thug Life
Starting at level 3, you gain proficiency in the Athletics or Intimidation skills (if you already have proficiency in both, you may pick a different skill to gain proficiency in). In addition, when you make an Athletics or Intimidation check, you may add +1d6 to your roll.
Dirty Fighting
Your unarmed attack damage is increased to 1d4, and your improvised weapon damage is increased to 1d6. You can now also sneak attack with unarmed strikes, any weapon with the light property, or an improvised weapon.
When a creature within 5' of you makes an attack, you can expend a reaction to make a dirty trick attack on either the attacker or the creature attacked. Once you have made a dirty trick attack on a creature, you cannot do it again until you complete a short or long rest. This dirty trick attack must be made with an improvised weapon or an unarmed strike.
If the dirty trick attack hits, you can cause the triggering attack to have advantage or disadvantage (your choice).
Strong Arm
At 9th level, the first time you hit a creature with a melee attack on a turn, you can attempt to initiate a grapple. When you have a creature grappled, your attacks on the creature are at advantage.
In addition, you can use your Cunning Action to make an Charisma(Intimidation) check on a creature (this check is at advantage if the creature is at half HP or less) opposed by either a Wisdom Save or their Wisdom(Insight) check (their choice). If you are, the creature becomes Frightened of you for 1 minute. If failed, you cannot attempt this on the same creature until 24 hours have passed.
Gang Leader
Starting at 13th level, when a creature makes an attribute check with a skill you have proficiency in, as a reaction you can add +1d6 to their roll. In addition, a creature offering you cover from an attacker may subtract 2d6 damage from any attack that hits them from the attacker.
Gotta have a Code
Starting at 17th level, you are immune to effects that attempt to charm, frighten, mentally control you. In addition, divination effects that attempt to read your mind or determine if you are telling the truth give the information you choose.
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This is an iteration on
's Thug above.
Self-comments:
Dirty Fighting is probably too strong. I tried to limit it to 1/creature per fight to make up for it.
Gotta have a Code is an attempt at T4 "gang thug" inspired by Omar from the Wire.
Gang Leader is utility; adding to checks, plus reducing damage to people who protect you.
Strong Arm, I like grapple; making it automatic means you can fold it into Dirty Fighting.
The "threaten" mechanic is needed; makes Intimation combat worthy. I'd almost rather drop the grapple than the intimidation. Both of them are T1/T2 feel abilities, so putting them in T3/4 seems wrong.
Upping damage to 1d4/1d6 is a ribbon mostly. Forcing improvised weapons on Dirty Fighting means that dice matter a bit. It also means resist/immune non-magic damage is going to make Dirty Fighting not as good. I think I'm ok with that?