After witnessing the heist of the Bank of Liberty (carried out by Niko Bellic and Packie McReary), Luis Fernando Lopez enters the loft of his employer, owner of successful clubs Maisonette 9 and Hercules “Gay” Tony Prince. Tony is in serious financial trouble, having taken out massive loans from the Ancelotti crime family and Mori Kibbutz in order to keep his clubs running. He asks Luis to work for Mori Kibbutz ( who is actually Brucie’s older brother) and Rocco Pelosi, an Ancelotti gangster, in order to satisfy his debts. Luis soon becomes acquainted with Yusuf Amir, an Emirati real estate developer who is interested in purchasing and franchising one of Tony’s clubs, and Ray Bulgarin, a Russian crime lord he met in the clubs. Tony also plans to buy two million dollars worth of diamonds in order to sell them at a higher price, but members of The Lost Motorcycle Club intervene the trading and steal them, resulting in the death of Tony’s current boyfriend Evan Moss.
Luis manages to intercept a meeting to trade the diamonds and recovers them. Bulgarin soon reveals that the diamonds are his property, and believes that Luis and Tony colluded to steal them, marking them for death. Giovanni Ancelotti orders that the diamonds are to be used as a ransom payment for his daughter Gracie, who was kidnapped by Niko Bellic and Patrick McReary. Rocco meets with Luis, and suggest that he should kill Tony in order to gain favor with Bulgarin, so that he will spare him. Though he contemplates doing so, Luis ultimately refuses and escapes Tony’s club when Russian gangsters sent by Bulgarin assault it. Luis travels to Firefly Island to disrupt Russian drug operations and cuts off his main cash flow, and learns that Bulgarin is fleeing the city by plane within two hours. With the help of Yusef (who kills Bulgarin’s henchmen attacking Luiz to stop him boarding Bulgarin’s plane) with his Buzzard attack chopper, Luis manages to board the plane, and kills all of the henchmen on board. A vengeful Bulgarin emerges from the cockpit holding a grenade, threatening destruction to both of them if Luis kills him. Luis takes the risk and shoots Bulgarin.
A dying Bulgarin drops the grenade causing the entire plane to explode. Luis parachutes out of the burning wreckage of the plane to safety, and heads to Meadows Park where Tony is waiting . Once there, they both tell Yusef, who has arrived at the scene, that they won’t franchise the clubs since they prefer to keep it a “family business”. In a small twist ending, the diamonds continually fought for are found by a homeless man in the trash. Like The Lost and Damned, the story of the Ballad of the Gay Tony also intertwines with the main story of Grand Theft Auto IV, as well as The Lost and Damned. The first main part of the storyline that intertwines is the diamond deal. A cook aboard the ship Platypus finds the diamonds (as seen in the opening credits of Grand Theft Auto IV]], and the deal between Tony and the cook is disrupted by the Lost motorcycle club, also shown in the Lost and Damned. The second deal at the Libertonian with Isaac is also shown in both DLCs, as well as Grand Theft Auto IV.
The trading of the diamonds in exchange for Gracie also is in both Grand Theft Auto IV and the game, as well as the aftermath of the diamonds, which had fallen into a dump truck, seemingly finding their way into a trash can, later found by the homeless man. Yusef Amir is mentioned briefly by Playboy X in Grand Theft Auto IV during the mission in which Niko and he attempt to take back one of his construction sites. Gay Tony is also briefly mentioned by “French” Tom Rivas, who talks about his bankruptcy. The big heist of the Bank of Liberty also features both Niko and Luis.