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
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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.