The deal whisperer: Inside the rise of Raine Group’s Jeff Sine

From humble beginnings, Jeff Sine built a career as an unorthodox banker who offered unvarnished advice and tamed unruly transactions for business moguls like Masayoshi Son and Rupert Murdoch. He defied the odds and built merchant bank The Raine Group into an investing empire in its own right.

Insider spoke with 10 people who have worked with Sine throughout his career, including senior bankers and clients. They explained how Sine became one of the world’s most influential dealmakers, the origins of his relationships with Masa and other key clients, and how he built a billion-dollar business.