johnathan o’Leary

Tiffany

Tiffany “Tiff” Callahan was born male in South Boston in the late 1970s, the only child of a hard-drinking dockworker and a woman who had worked the Combat Zone under the name Tiffany before she got knocked up and tried (and failed) to go straight. His mother kept the working name even after she married. She was loud about it. When the baby came out with a cock, she still insisted on Tiffany. “That’s my name. That’s the only pretty thing I ever had. He’s getting it.” His father was too drunk or too scared of her to argue. The birth certificate read Tiffany Francis Callahan. The kids on the block never let him forget it. Growing up with a girl’s name in that neighborhood meant constant fights. He learned early that the only way to stop the laughing was to hurt people first and harder. By sixteen he was running numbers and collecting for a mid-level Irish crew. The name became a weapon. “You got a problem with Tiffany?” usually ended with someone spitting teeth on the pavement. The older guys started calling him Tiff the way you’d call a particularly vicious dog by a soft name—half joke, half respect. He was smart enough to get out of the street-level shit. Night school, community college, then law school on scholarships and dirty money. While other associates were still cracking skulls, Tiff was learning how to make evidence disappear, how to lean on witnesses without leaving marks, and how to keep the books clean enough that the Feds couldn’t touch them. By the time he passed