| Platinum | Overachiever | Collect all trophies | 0.1% Ultra Rare | 14,332 pts |
| Silver | Elvira Duarte, No. 1 | Win as Elvira Duarte | 0.2% Ultra Rare | 3,546 pts |
| Silver | Maggie Dyer, No. 1 | Win as Maggie Dyer | 0.2% Ultra Rare | 3,546 pts |
| Silver | Stephanie St. Clair, No. 1 | Win as Stephanie St. Clair | 0.2% Ultra Rare | 3,546 pts |
| Gold | Lone Wolf | Finish the game without recruiting a gangster | 0.3% Ultra Rare | 3,707 pts |
| Silver | Dean O'Banion, No. 1 | Win as Dean O'Banion | 0.3% Ultra Rare | 2,780 pts |
| Silver | Joseph Saltis, No. 1 | Win as Joseph Saltis | 0.3% Ultra Rare | 2,780 pts |
| Silver | Frank Ragen, No. 1 | Win as Frank Ragen | 0.4% Ultra Rare | 2,339 pts |
| Silver | Mabel Ryley, No. 1 | Win as Mabel Ryley | 0.4% Ultra Rare | 2,339 pts |
| Silver | Salazar Reyna, No. 1 | Win as Salazar Reyna | 0.4% Ultra Rare | 2,339 pts |
| Silver | Sai Wing Mock, No. 1 | Win as Sai Wing Mock | 0.4% Ultra Rare | 2,339 pts |
| Silver | Angelo Genna, No. 1 | Win as Angelo Genna | 0.5% Ultra Rare | 2,046 pts |
| Silver | Goldie Garneau, No. 1 | Win as Goldie Garneau | 0.6% Ultra Rare | 1,834 pts |
| Silver | Frankie Donovan, No. 1 | Win as Frankie Donovan | 0.7% Ultra Rare | 1,672 pts |
| Silver | Daniel McKee Jackson, No. 1 | Win as Daniel McKee Jackson | 0.9% Ultra Rare | 1,438 pts |
| Gold | Bulletproof | Finish the game without getting anyone in your crew killed | 1.1% Ultra Rare | 1,700 pts |
| Silver | Alphonse Capone, No. 1 | Win as Alphonse Capone | 1.3% Ultra Rare | 1,153 pts |
| Bronze | I'll Be Back | Have someone in your crew go to jail | 2.7% Ultra Rare | 496 pts |
| Bronze | You Know Who I Am | Kill Alphonse Capone | 4.3% Ultra Rare | 375 pts |
| Bronze | Closed Casket | Kill Daniel McKee Jackson | 4.6% Ultra Rare | 360 pts |
| Bronze | Public Enemy 1 | Became Enemy of the State while maintaining the highest notoriety | 4.6% Ultra Rare | 360 pts |
| Bronze | Curtain Call | Kill Goldie Garneau | 4.9% Ultra Rare | 347 pts |
| Bronze | The Irish Goodbye | Kill Frankie Donovan | 5% Very Rare | 343 pts |
| Bronze | The Ice Queen Go-eth | Kill Mabel Ryley | 5% Very Rare | 343 pts |
| Bronze | Shoulda stayed in Sicily | Kill Angelo Genna | 5.1% Very Rare | 339 pts |
| Bronze | The Lion Sleeps Tonight | Kill Maggie Dyer | 5.2% Very Rare | 335 pts |
| Bronze | It's just Business | Kill Frank Ragen | 5.2% Very Rare | 335 pts |
| Bronze | Luck of the Draw | Kill Stephanie St. Clair | 5.2% Very Rare | 335 pts |
| Bronze | Like Shootin' Ducks in a Pond | Kill Sai Wing Mock | 5.3% Very Rare | 331 pts |
| Bronze | Last Call | Kill Joseph Saltis | 5.4% Very Rare | 327 pts |
| Bronze | Into the Sunset | Kill Salazar Reyna | 5.5% Very Rare | 324 pts |
| Bronze | Pushing Daisies | Kill Dean O'Banion | 5.7% Very Rare | 317 pts |
| Bronze | Flor de Muerto | Kill Elvira Duarte | 5.9% Very Rare | 310 pts |
| Bronze | Trust Me | Land a hit with 10% or lower odds | 11.7% Rare | 206 pts |
| Silver | Maximizer | Get a hotel and have all synergies simultaneously | 15% Rare | 266 pts |
| Bronze | There Goes the Neighborhood | Took over a neighborhood | 15.9% Rare | 171 pts |
| Bronze | This Never Happened | Bribe a cop | 16.4% Rare | 168 pts |
| Bronze | Jack of All Trades, Master of None | Own five of each racket type | 16.5% Rare | 167 pts |
| Bronze | I Know A Guy | Hire a gangster of each profession | 18.3% Rare | 157 pts |
| Bronze | Reliable | Max the loyalty of one member of your crew | 18.7% Rare | 155 pts |
| Bronze | I've Got Your Back | Form a Business Arrangement | 27.6% Uncommon | 123 pts |
| Bronze | My Specialty | Get a synergy bonus | 30.2% Uncommon | 116 pts |
| Bronze | Let This Be A Warning | Perform an execution | 36.3% Uncommon | 104 pts |
| Bronze | On My Own | Complete the tutorial | 37% Uncommon | 103 pts |
| Bronze | Whacked | Kill Ronnie O'Neill | 39% Uncommon | 100 pts |
| Bronze | Bullseye | Take down an enemy with a single shot | 49% Common | 87 pts |