Think of a movie or book you love where not a single character, not even the hero, is truly virtuous. For old-timers like me, “The Sting” (you know, starring Robert Redford) immediately comes to mind. For literary types, “The Talented Mr. Ripley” by Patricia Highsmith. Both are about con artists, though the crooks in “The Sting” are fun and are just ripping off illegal gamblers, where Mr. Ripley is, well, pretty much everything that personifies awfulness. The fact is that there are compelling anti-heroes for all literary tastes, the common ingredient being that we somehow end up rooting for them despite their criminality. What is the point of works like this–what are we supposed to do with them? Now that I’m working on a novel about a professional rumrunner during Prohibition (based very loosely on my grandfather), these questions are beginning to haunt me.

One of my favorite contemporary philosophers, Nomy Arpaly, writes about people and characters who do good with no principle of virtue about them (Unprincipled Virtue: An Inquiry into Human Agency). Probably her best example is Huck Finn, who does the right thing by protecting the slave Jim not because Huck objects to slavery, but simply because his friend Jim asked him to. In fact, Huck knows he is breaking the law and believes he is doing wrong by protecting a slave. Yet in the greater context of antebellum slavery, Huck does a heroic thing, even though he is an equivocally heroic character at best.

My current literary obsession, Anthony Trollope, was an expert at this, and he was explicit about it. A good example is The Small House at Allington, one of his Barchester novels. Even the closest reader would be hard pressed to find a true hero in this novel. The two best candidates, Lily Dale and Johnny Eames, lose out because….well, I don’t want to give the ending away. At the novel’s opening, Trollope openly states that the search for a hero in this novel is bound to be frustrated: “Whatever of the magnificent may be produced will be diluted and apportioned out in very moderate quantities among two or more, probably among three or four, young gentlemen—to none of whom will be vouchsafed the privilege of much heroic action.” (Ch. 2)

This approach is even truer in one of Trollope’s cleverest plots, in Mr. Scarborough’s Family, which is essentially about a crime that–legally speaking–lacks both victim and perpetrator. Mr. Scarborough has found a loophole in the English inheritance laws governing his estate and by doing so evades the ruinous debt accumulated on this property, issued at usurious interest. (By nefarious Jews, of course. If you read Trollope you have to endure his anti-Semitism. Maybe that’s worthy of another post.) Everybody in the novel, except the old reprobate Scarborough, agrees that a wrong has been done. Nobody can agree how to correct it or who should be compensated. The point of the novel, I think, is that when the laws themselves are obsolete or corrupt, virtue becomes a matter of theory rather than fact and agents of virtue are, by force, equivocal. But another point is that no person can be above the law and still be virtuous, even when social change renders those laws problematic.

Which brings me to Prohibition and Dorry Yosell, the rumrunner in my novel, The Mayor of Newark. Or, for that matter, to my grandfather, Abe Poznak, the real-life rumrunner who inspired him. Like my grandfather, Dorry inherits a legitimate trucking business that, because of Prohibition, evolves into a liquor-transporting business more or less as a survival strategy. Dorry employs a lot of people and is generous and supportive to his his employees. He eschews violence and deplores the law that made all of this happen. Yet he consorts with gangsters, some of whom will, historically, end up committing horrific crimes. (At one point Meyer Lansky gives Emma Yosell, Dorry’s wife, a diamond bracelet. This actually happened to my grandmother.) So is Dorry wrong to stay in this business? Is he really doing anything morally objectionable? Should he just abandon his employees and their families? Can he be a felon and still be honorable? Trollope, I think, would say no. But you’ll have have to stay tuned and decide for yourself.