Broken tombstone - grave digger

Pile of bullets with "Dibs" written over it - Rogue

Dynamite/moltov pile - HQ buster

A group of men being knocked down like bowling pins for BG killer etc

IS THIS RIGHT? 

Winnabego with smoke coming out of it - DF Profit

Jail window with bent bars/wall with a toilet shoved to the side with a hole in the brick wall - JBing 

Back pocket with a hand in it, wallet half out, few bills flapping free possibly - PPing

Jail Bars over the word "Omerta" or something - Family JBing 

Tiny Image of the durdents with bullet holes in their head - NPC for basic levels, then Marla, Robert and then Tyler at the top for Max. So the image changes as  you increase rank. 

Felony - Pile of paintings leaning against a wall, jewels/necklaces and bags of money draped over/on the ground

Felony - A pile of boxes on fire next to a car, arsonist. the higher teir results in a building on fire

OC - Hands in a circle like before a sports game "GO TEAM!" but its like "COMMIT CRIME!" or something. 

City achivements - Tiny map, all cities marked with * for the completed one. So like 50 NY/DT would have 2 stars in those locations etc 

CA Cocaine - A tiny table with an envelope under it and a tiny handcuff key next to it

Just a purse with money sticking out. - Purse Pilferer

A cash register with money sticking out. - Shaft a Schlub

Most of mine seem to be money sticking out themed.

A red light - corner contractor.

Just a pick lock - Picking Perfectionist

Just an open safe - Superior Safecracker.

A Cannoli. Not sure what it would represent though. My brain is without coffee right now.

Bank Booster can probably be a silhouetted duffel bag.

Molotov cocktail for domicile destroyer

Would probably just do a generic painting of something (or, a small painting of a portly man in a Napoleon outfit standing next to a horse) to represent Picasso pilferer.

Lockup Liberator/jailbreaking achievement could be some bars that have been sawed off? (Or a picture of Rita Hayworth?)

what are all the other acheivements going to be? i think your man is francis by the sounds he has got a pretty good idea on symbols for all you got going on

A Tommy gun. An icepick. A fedora. A shoeshine box. A crate of moonshine bottles. The Godfather marionette. A godfather's pinky ring. The burning photo of the saint with a smear of blood. 

Oh snap, that picture you posted looks pretty cool.

What kind of style of you going for.. is more serious or jokey?

Things probably already thought about but:

- open suitcase full of cash

- knuckle duster

- clenched fist with or without tattoos on

- baseball bat

- smashed up car

- person in a wheelchair/chair

Ace of spades or dice for something connected to gambling- obviously not all casinos are connected to the mob, but there was a lot of overlap there.

Seeing a lot of cool ideas here, I won't input as mine would be unoriginal and perhaps inappropriate. I do believe kaya deserves a kayak trivia trophy though

Jail - Broken jail bars off a cell with someone getting out

Travel - Private plane

Drugs - Just a variety of people getting high. I think that'd be pretty funny

CAs - Gangster putting money in a police's pocket whilst he's getting cash in an envelope from a policeman. 

OCs in every city - Basically a planning room where you can clearly see the 6 cities.

Other OCs - Same idea as the drugs: A variety of trophies that represent the theme of the OC: ex: Someone carrying a big painting for the art gallery. A truck with money kinda flying out from the truck depot, etc.

Trying to think of a couple more images that say "mafia" to me: I think one of the biggest ones would be a pistol with a silencer? (Makes me think of James bond too, but definitely mafia as well.) 

Also, to go along with the "sleeping with the fishes" could be a fish with it's eyes as X's?

Not sure anything gambling related would be a good achievement, whilst the majority are probably responsible I can only assume as there is a self-limiting option that people have went OOT with gambling, an achievement might encourage it more if amounts greater than the daily hustle are involved.

Purse Pilferer - old lady, something like this but in the site colours and obscured.

https://www.vectorstock.com/royalty-free-vector/senior-fashion-lady-holding-purse-vector-13684676

And a couple of new possibilities based on game mechanics.

Name: "Under my wing"

Icon: Large mafioso standing with, or sheltering under their trench coat, a youngster

Description: Sponser X members, available to only Wise Guy. (one off, or incremental)

Reason: Sponsors do, for the most part, work hard.  There is an art to properly recruiting people.

Name: "Showing tribute"

Icon: "Wad of rolled up dollars"

Description: Paid X amount in taxes (incremental)

Reason: Taxes generally seem to be something that always were a burden to get.  There is the hustle, but if there was a benefit (achievement) people might pay.  Perhaps it's not as big an issue.

Name: "Up on my soapbox"

Icon: a soap box!

Description: Contribute to the Streets or BD X times in a thoughful way

reason: Just might be a nice idea.