Note: This is a missable achievement. If you are planning on getting all achievements, you will require a minimum of two playthroughs each with a different strategy.
One strategy would keep all underbosses alive (required for this achievement), flip all racket bosses, and recruit 15 informants. The second strategy would keep
only one underboss alive (causing you to miss this achievement), kill all racket bosses, and kill 15 informants.
To get this achievement, you must keep Cassandra, Vito, and Burke allied with you. You do this by splitting the18 rackets and 9 districts equally between these three underbosses. Plan in advance. Decide who is to get what district and assign the rackets in that district to the underboss who is to get the district.
Assigning a racket to one underboss and, later, the district it is in to another results in the first underboss losing the racket and the second underboss gaining it. The first underboss reacts with great animosity that could jeopardize the alliance you are trying to maintain for the achievement.
Story progression assigns Delray Hollow to Cassandra, River Row to Vito, and Pointe Verdun to Burke. The rackets in these districts are also assigned by story progression to the underboss of the district. The player is able to choose to whom to assign the twelve remaining rackets and six remaining districts. Since the underbosses have more affinity to certain districts than others, it is best to make the racket and district assignments as follows:
(Format: Racket & Racket->District)
--Cassandra: Garbage & Guns->Barclay Mills, Southern Union & PCP->Frisco Fields
--Vito: Construction & Blackmail->Downtown, Sex & Drugs->French Ward
--Burke: Auto Theft & Smuggling->Tickfaw Harbor, Gambling & Black Market->Southdowns
If all 18 rackets and 9 districts are assigned equitably, the achievement will unlock immediately following the sitdown where the ninth district is assigned. The below video shows the achievement unlocking as Lincoln walks outside following the sitdown where he assigned the ninth district:
Note: This achievement and the one below are mutually exclusive and must be obtained in separate playthroughs: