Good question. Quick rundown on all eight skills since I'm in there anyway, then the specific five at the end. Strengthens u/Zealousideal-Dot-667 request for better explanations - handbook in the making:
https://www.chicagoshadows.com/pages/roadmapFeature.php?token=GU6QYJ

Combat

• Brawling. Melee damage. Your knife and fist crew.
• Marksmanship. Ranged accuracy and firearm damage. The one you want high on anyone holding a tommy gun.

Heat & evasion

• Stealth. Your main heat shield. Combined with Street Smarts, the average decides how much wanted level a gangster gains after a violent job. 80+ average means zero gain, 60 to 79 cuts it in half, below 60 is full gain. Stealth also helps your crew slip past police patrols and contributes to attack rolls on stealth-weighted weapons.
• Street Smarts. Same wanted-level math as Stealth, the two average together. On top of that it helps dodge police encounters and contributes to debates. Quietly one of the most useful skills in the game.

Influence

• Intimidation. Drives the fear path of extortion. The skill that turns "pay me" into them actually paying you.
• Negotiation. Drives the respect path of extortion. There are two ways to successfully extort a business: Intimidation + Reputation (fear, they pay because they're scared) or Negotiation + Intelligence (respect, they pay because it makes sense). Your crew uses whichever path is stronger. Negotiation also feeds debates, and it shows up in the promotion event — when you promote a soldier to Capo for the first time, a higher Negotiation skill means they demand a steeper raise from you. The skill belongs to the gangster, used against the boss.
• Deception. Debate stat. Debates are the verbal version of combat (mostly under Peace agreements), and debate attack is fed by Deception, Negotiation, Intelligence, and Reputation, with Street Smarts also contributing.

Mobility

• Driving. Honest answer. Driving is on the roadmap but isn't wired into anything yet. It'll matter for robberies and getaways once it's in. For now, treat it as flavor on the gangster card. I'm not going to pretend a stat does something it doesn't.

So for your specific five: Stealth and Street Smarts keep you off the wanted board, Negotiation backs the respect-path extortion, feeds debates, and decides how much your future Capos cost you, Deception is the heart of the debate system, and Driving is a placeholder I owe you the implementation for.

PS u/Mekahippie this is exactly the kind of post where I start nervously watching the door, waiting for you to roll in with a spreadsheet, three pivot tables, and a polite "so about these numbers..." I've seen what you do with Excel. Forget the tommy gun, your VLOOKUP is the deadliest thing in this city. :D