The father figure is Leonard, the high-living, recovering coke addict, "West Coast Director of a large Italian-American finance firm" (read: mobster) who helped to keep James Frey clean in A Million Little Pieces. The son is, of course, James, damaged perhaps beyond repair by years of crack and alcohol addiction, and by more than a few cruel tricks of fate.

James embarks on his post-rehab existence in Chicago emotionally devastated, broke, and afraid to get close to other people. But then Leonard comes back into his life, and everything changes. Leonard offers his "son" lucrative, if illegal and slightly dangerous, employment. He teaches James to enjoy life, sober, for the first time. He instructs him in the art of "living boldly", pushes him to pursue his passion for writing, and provides a watchful and supportive veil of protection under which James can get his life together. Both Leonard's and James' careers flourish, but then Leonard vanishes. When the reasons behind his mysterious absence are revealed, the book opens up in unexpected emotional ways.

My Friend Leonard showcases a brilliant and energetic young writer rising to important new challenges, displaying surprising warmth, humor, and maturity, without losing his intensity. This book proves that one of the most provocative literary voices of his generation is also one of the most emphatically human.