"Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success" by Russ Buettner and Susanne Craig is an investigative account of Donald Trump’s finances, drawing on decades of tax records, business documents, and insider testimony. The book argues that Trump’s public image as a self-made billionaire is largely a myth, built on vast financial support from his father, Fred Trump, and sustained through risky ventures, bailouts, and strategic branding. Instead of growing his inheritance, the authors show how Trump repeatedly lost money through failed casinos, troubled real estate projects, and poor business decisions, only to be rescued by luck, lenders, or television fame. Ultimately, the book portrays Trump’s career not as one of shrewd entrepreneurship, but as a story of squandered fortune and a carefully constructed illusion of enduring success.