Events of GTA Online
If the Online Player clears five Gang Attacks against The Professionals in a single Free Mode session, The Boss will send a text to them stating that "You won't even see them coming" and a random value bounty will be issued on the player's head.
Events of GTA Online: The Diamond Casino & Resort
|This article or section refers to "enhanced version" content in the Xbox One, PlayStation 4, and PC renditions of Grand Theft Auto V and/or Grand Theft Auto Online, that is absent on the Xbox 360 or PlayStation 3 versions.|
For a complete list of the features of the "enhanced" version of Grand Theft Auto V, please see here.
In 2019, He appears in person in the Casino Work mission "Department of Defense". Under Agatha Baker's orders, the protagonist must defend The Diamond Casino & Resort, as it is attacked by The Professionals. They are standing south of the casino and after they are killed by the player, a Speedo must be followed to a location where more of them are waiting. The Boss is also there, wearing Ballistic Equipment armor. The protagonist has to kill him, along with all other members of the Professionals.