Base Class: Rogue
As leaders of dubious and morally questionable organizations, Kingpins are excellent negotiators, liars, and combatants should the occasion require it. Every Kingpin has their secrets, and living with plenty of people who want your head on a platter has granted you clever means of obtaining and keeping information. Additionally, leading conflicts in contested territory, either with other gangs or the local law, has granted you clever battle tactics and the ability to recognize opportunities to help your allies in battle. And although social manipulation is your forte, you still know how to take matters into your own hands as your lackeys have blundered jobs before. After, all if you want something done right, you have to do it yourself. Your established or perhaps growing reputation has earned you the luxury of confidence, and you are not afraid to stand up in public despite the risk of being recognized as the criminal you are. And finally, as is so easy for someone of your station, throwing someone under the proverbial bus and can make a chance at a dexterous switch of you and an enemy when an attack is headed your way.
Kingpin's Secrets
When choosing this archetype at level three, you learn the ability block out prying minds. Your thoughts can no longer be read and insight checks against you are made at disadvantage. You cannot put forth false thoughts, however, but you can choose to let this barrier go and allow someone to read your mind if you choose.
Master of Tactics
Starting at 3rd level, you can use the Help action as a bonus action. Additionally, when you use the Help action to aid an ally in attacking a creature, the target of that attack can be within 30 feet of you, rather than 5 feet of you, if the target can see or hear you.
Reputed Confidence
Starting at 9th level, your confidence propels you into battle. You can give yourself a bonus to your initiative rolls equal to your Charisma modifier.
You also gain an additional way to use your Sneak Attack; you don't need advantage on the attack roll to use your Sneak Attack against a creature if you are within 5 feet of it, no other creatures are within 5 feet of you, and you don't have disadvantage on the attack roll. All the other rules for Sneak Attack still apply to you.
Under the Bus
Starting at 13th level, and once per short rest as a reaction, you may convince or force a creature within 10 feet of you take an attack intended for you. Targeted creature must make a Charisma Saving Throw of DC 14 or be convinced to take the attack, or you may make a contested Dexterity check to force the creature to take the strike for you instead. You cannot make the original attacker take the attack for you, but the creature you choose does not have to be specifically an enemy or ally, it may be any creature either in the initiative line or small or larger. Your Charisma modifier is added to the ability's DC, and creatures large, huge, and gargantuan have +1, +3, and +5 added to their contested Dexterity Check respectively. If the targeted creature succeeds, your reaction is taken, but your ability to use Under the Bus for the Short Rest is not taken.
Do it Yourself
If you want something done right, you have to do it yourself. At 17th level, three times per Long Rest, if you are the only Ally within 5 Ft of an Enemy, you may turn a normal hit into a Critical Hit before you roll for damage. If this is done as a sneak attack, add two extra d10 of damage to the attack's damage after doubling the damage for the Critical Hit.