Though Shkreli seems uniquely modern, Balleisen told me, there are many parallels between him and other American fraudsters before him. I talked with Balleisen about some of those parallels and about how financial crime has changed in the past century. The conversation that follows has been edited for length and clarity.

Joe Pinsker: When I heard about the verdict last week, you were one of the first people whose thoughts I was most curious to hear—Shkreli seems to be such a product of modernity, but I figured you’d be able to place him on more of a historical timeline.

Edward Balleisen: One of the elements of the case that stands out for me is the awareness, on the part of both the prosecution and the defense, of how much of the issue is dependent on defining the public image of Shkreli. So how do we make sense of him: Is he a ruthless predator, a congenital liar, a backpedalling conniver? Or alternatively, is he a well-meaning iconoclast who's focusing on this big social need around orphan drugs and niche diseases that doesn't get enough attention?

There's this battle for how to make sense of him that's actually quite resonant with many, many different public controversies around allegations of fraud, going back decades. There’s some resonance, perhaps, with a person like Preston Tucker, the car magnate who confronted allegations of fraud in the late 1940s—in that case, allegations that were unable to convince the jury to convict. There were clear elements of aggressive puffery, in the kinds of promises that Tucker and his company made to would-be dealers in his network, as well as to potential customers. And so one of the issues that emerged there was, was this just optimism that turned out to be misplaced, or did it involve intentional deceit? That's always a really difficult issue, especially in a case where there are complex facts and where things may look different at one point in time than they do once misfortune strikes. That's one comparison that comes to mind.

Pinsker: What are some others?

Balleisen: Another one would be with E.G. Lewis, who was a very aggressive entrepreneur in the early 20th century, operating out of St. Louis and pushing all kinds of aggressive new business models, including a mode of banking by mail. He developed a publication empire focused on very low-priced periodicals aimed at rural women. It wasn’t at all difficult to find specific actions of his that look deceptive. But the question around Lewis, in the end, really focused on how to make sense of the totality of the business.

One of the real parallels between Lewis and Shkreli is a focus on using innovative modes of communication to shape the public debate about their own business practices. So where Shkreli is livestreaming and tweeting, in Lewis's case, he was using the platform of his own magazine and press to churn out very aggressive narratives about the nature of his business efforts, and about the antagonists who he depicted as trying to pull him down.