What emerges strikingly is the portrait of a swindler who, although admitting what he has done, is more concerned with what is happening to him than in the moral issues involved. He is shaking his head at how he could have ever done such a thing and ruined his life, but he is worried about what kind of prison he’ll be sent to and the kind of food he’ll get. He is pictured having close moments with his son, behaving as a father might without all the baggage with which the son must deal—just a regular dad with a problem—and his son seems loyal.

Simon has a sharp eye for telling details. He films consultations between Dreier and his lawyer to decide what kind of statement to make to the sentencing judge to get the best possible deal in light of the fact that he could get the 145 years demanded by the prosecution. Dreier exhibits some of the chutzpah that got him into committing the crimes in the first place. He wants to tell the judge that others did worse. His lawyer advises him that this would be the wrong way to go and only alienate the judge.

The film seeks through interviews and observations to find the key to the man. The clearest portrait comes from Dreier himself. He doesn’t know how he went as far as he did, but at the same time, one may feel that he is proud of his skills that he now wishes were put to honest use instead of taking him down the path to crime in quest of a high lifestyle.

We learn that Federal Judge Jed Rakoff sentenced Drier to 20 years in prison. While the judge said “He is not going to get any sympathy from this court,” he also said that “he is no Madoff under any analysis.”