Jeffrey Siger was born and raised in Pittsburgh, Pennsylvania. He received degrees in political science and biology from Washington and Jefferson College, and in law from Boston College Law School (together with the academic honor, Order of the Coif).

He began practicing law at a major Wall Street law firm. While there, he helped establish New York City's leading organization for private-practice lawyers seeking to volunteer for public service, and served as Special Counsel to the citizens group responsible for reporting on New York City's prison conditions. His investigation into a politically charged suicide in one of its jails resulted in a report The New York Times covered as its lead, front page story, and Newsweek magazine called the greatest example of the newest form of unofficial art, the Investigative Report.

He left Wall Street to join his own New York City law firm. There he continued as one of its name partners-litigating high-stakes society scandals and other delicate public and private matters of domestic and international consequence-until giving it all up to write full-time among the people, life, and politics of his beloved Mykonos, and spearfish in its Aegean waters.