Jerry first appeared as an unnamed tramp in the cutscene during "Clean Getaway." He was hanging out in Hove Beach and begged Vladimir Glebov for some spare change while Vlad was walking with Niko to his car.
After the exchange of Gracie Ancelotti for the Diamonds, the diamonds everyone was after were thrown onto a passing truck. Kapowitz had been living near the Liberty City dump and surviving off of things he salvaged from there when he stumbled upon the diamonds valued at over $2 million in Meadows Park after accidentally bumping into Luis Lopez.
Kapowitz plans to take his wealth down to Vice City where he will start a gun shop and liquor store. His ownership of the diamonds was immediately contested by over 100 people. Mayor Julio Ochoa decided that it would be impossible to verify the claims, so he allowed Kapowitz to keep all of the proceeds from the diamonds' sale. He is seen during the closing credits of The Ballad of Gay Tony, celebrating his fortune in the back yard of Bryce Dawkins' mansion in Westdyke, Alderney with a few people, apparently prostitutes and Kay Hartman.
- GTA IV
- The Ballad of Gay Tony
- In the news media in GTA IV, it is said that Kapowitz found the diamonds in the city dump. However, this is seemingly retconned in The Ballad of Gay Tony where in an updated version of the story states that he found them in the trash in Meadows Park (as seen in the closing cut-scene of the mission "Departure Time"), likely due to the fact that there is no dump anywhere in Liberty City.
- Jerry is still wearing his tramp attire while celebrating at his mansion in the credits of The Ballad of Gay Tony.
- When Jerry discovers the diamonds, he holds them up in exactly the same way that The Cook did in the first cutscene of GTA IV.