Clarence Darrow exists foremost in the public memory as Spencer Tracy, who played a lawyer based on Darrow in the 1960 movie Inherit the Wind. That film, in turn, was based on Darrow’s 1925 defense of a Tennessee educator accused of breaking a state law banning the teaching of evolution in public schools. (Darrow lost The State of Tennessee v. Scopes, or the “monkey trial,” as it was known; the law was later repealed.) But as John A. Farrell makes clear in his new biography, Clarence Darrow: Attorney for the Damned, Darrow’s life was even more tumultuous than that sensational trial would suggest.

Before Darrow became the champion of labor, proponent of the poor and defender of the most hopeless of death-row cases, he was a corporate lawyer—and for a railroad, no less. What turned him away from a career as a fat cat?

He couldn’t look at himself in the mirror. He was at heart one of the most compassionate people you could imagine meeting, and that part of him was always at war with the striver, the go-getter. But whenever the chips came down, they always came down on the side of the guy who needed a good lawyer. Depending on how he was fixed at any given time, a third to a half of his cases he was handling for free for indigent clients. He didn’t charge big fees for his most notorious clients if there was a good cause behind it. It was just conscience, basically, that forced him to give up that job as counsel for the Chicago & North Western Railway. He was also prompted by his boss, his patron at the railroad, who had a sudden heart attack and died, so Darrow’s decision was helped along by the fact that he no longer had a career there.

He operated for a while as a political lawyer in Chicago when the words “politics” and “Chicago” were pretty much synonymous with “graft” and “corruption.” How did he avoid the taint of that time and place?

He didn’t, entirely. He got involved in several of the scandals of the time, but even crooked politicians need a good lawyer, and sometimes the law is applied in courts that are straight. So there was a respect for Darrow among the political boys for his ability to actually get things done, to run things, while they pursued their tricks and their deals. At the same time he was an idealist, and in fact one of the movers in the attempt by the Populists to spread their campaign from the farms, where it was born, to the cities.

Of course, William Jennings Bryan became Darrow’s most famous foil during the monkey trial. Yet the two men were aligned in the 1896 presidential campaign. What brought them together, however briefly?

You had the growth of the Populist movement—a widespread feeling out in the West and Midwest that the financiers of the East were using the gold standard to keep the average farmer and the average working man in poverty. For the first time, in Chicago in 1896 [at the Democratic National Convention], you had a major party declare that it was going to represent the poor. That was Bryan’s amazing feat of political rhetoric: he was this young, unknown congressman and he stood up there and he captivated that convention hall and brought the Populists and the Democrats together.

Darrow was part of that same movement, but he never particularly cared for Bryan as a person. He thought Bryan was too religious and basically too stupid to lead a major party, and it really grated on him that Bryan got the presidential nomination three times. So their rivalry began to simmer and fester, and when Darrow had a chance to ambush Bryan in the courtroom in Dayton, Tennessee, in 1925, he took full advantage of it.

In Darrow’s day there was open warfare between labor and capital. He stepped into that war in a major way in Idaho in 1907, when he defended Big Bill Haywood and two other unionists charged with murdering a former governor. You write that, “Of all of Darrow’s courtroom speeches, his summation in the Haywood case was arguably the most brilliant, and dangerous.” In what way brilliant, and in what way dangerous?

It’s brilliant in its eloquence. In those days attorneys and prosecutors could speak for up to 12 hours, or even longer—Darrow, in the Leopold and Loeb case, spoke for three days. The Haywood summation is long, and to the modern ear it tends to wander, but you have to think of him standing in the courtroom and speaking to the jury, and going back and forth over his major themes like a weaver. That speech is amazing, for his ability both to tear apart the prosecution’s case and to draw from the jurors—who were not union men, but were working men—an appreciation for what labor was trying to do.

It was extraordinarily dangerous because he was using a plea for a client as a soapbox. He made a very political speech, talking in almost socialistic terms about the rights of the working class, and there was a danger that the jury would react against that—as one of his juries later did in Los Angeles. But it was a very small courtroom and the defense table was right up against the jurors; over the course of 90 days he got a very good sense of who they were, talking during breaks, listening to them, watching them as they listened to the testimony. I think it was an informed bet he was willing to make.

In that trial, there was a whisper that Darrow, or someone working for the defense, tried to bribe potential witnesses. And after he defended two brothers accused of firebombing the Los Angeles Times in 1911, Darrow himself was tried—twice—on charges that he’d bribed jurors in that trial. He was acquitted the first time, but the second case ended with the jury hung 8-4 for convicting him. So: Did he do it?

In the book I argue that he almost certainly did. It’s going to be a puzzle for historians forever; I don’t think we’re ever going to find one piece of paper on which Darrow wrote to one of his cohorts, “Hey, did you make sure you got the juror that bribe?” But all the evidence indicates—well, there certainly was an attempt by the defense to bribe jurors; the question is, to what extent did Darrow know about it and to what extent did he actually inspire it? One of the most compelling things for me was to find in his mistress’s diary from years later that she concluded he had the capacity to do it. She had been his most faithful supporter and had insisted on his innocence.

He was very careful in talking to his friends and family about the charges. He never actually said, “I didn’t do this.” He pled not guilty, but he believed that guilt was always a matter of motive and intent. And in this case he thought he had a good motive and a good intent because he was fighting for labor.

Darrow grew up on a hardscrabble farm in Ohio and told his friend Jane Addams, “I have never been able to get over the dread of being poor, and the fear of it.” But he had a pretty complicated relationship with money, didn’t he?

He did, and it got him into a lot of trouble. His law partner for a time was Edgar Lee Masters, the famous poet, and Masters said it was the money that ruined him. And Darrow did need money, because, for one thing, he was a womanizer. He was supporting two households—his first wife and their son, and then his second wife. It also cost money to run around chasing other women.

Another problem is that he was an awful investor. His second wife, Ruby, once wrote to one of his sisters and said, well, Clarence’s new idea is for a ranch in California, and I guess that’s better than an empty or gold mine or any of the other crackpot schemes he always jumps at. One of the sadder things about his life is that he finally got his money into a sound natural-gas company in Colorado, and when he sold his interest in the 1920s he had enough money to retire. And then he lost it all in the crash, so he had to go out in his 70s making speeches and public appearances and doing stunts like defending Benedict Arnold on the radio, just to keep the wolf away from the door.

And speaking of complicated relationships: as you said, Darrow was twice married and a serial philanderer. What was up between Darrow and women?

There is a philosophical consistency, in that he was an advocate of the free-love movement of his day. In Victorian America the times were so repressive, particularly for women. One of Darrow’s clients was a well-respected gynecologist from Chicago who wanted to write in the American Medical Association journal that it was okay to have pleasure from sexual relations. The other doctors in the AMA said no, we’re not going to say anything like that; sex is for procreation; it might be for pleasure if men can go to bordellos, but certainly not for women at home. That’s the kind of climate that the free-love movement moved against, and Darrow was a supporter of it. As far as I can tell, he was up front with his mistresses and the young ladies that he met in the free-love cause, and they agreed that this was a natural inclination and you shouldn’t try to repress it.

Politically, he was a very early feminist; he argued in the 1880s for giving women the vote. But later he soured on the suffragette movement because it aligned itself with Prohibition, which he hated. He didn’t speak or campaign against giving women the vote, but there was a marked loss of enthusiasm for what he had thought would be a very good thing for the country.

Darrow loved the company of friends and the balm of candid conversation, but at times some of his friends questioned his choice of cases and causes. Why?

There was a feeling, at least up until the trial in Los Angeles, that he was motivated by money, that he saw the opportunity for a very skilled labor lawyer and took it. You find newspaper editorials and people saying, for somebody who’s talking about the cause of labor, he sure is making a lot of money off the poor working man. But after Los Angeles and his disgrace, he had a second act, and it was redemptive. He represented an awful lot of indigent clients and took a lot of civil rights cases. The two major cases of his career came when he was in his 60s—the Leopold and Loeb case and the monkey trial. Also his defense in the Sweet trial, which is the key in deciding whether you like him or not.

After the monkey trial he was without a doubt the most famous trial lawyer in America. He could have commanded titanic fees from any corporation in America; they would have loved to have him. And instead, he used his fame to go to Detroit and represent for $5,000 over nine months a group of African Americans who had been trapped in a house by a racist mob at a time when the city was whipped into a hateful frenzy by the Ku Klux Klan. [The homeowner, an African American physician named Ossian Sweet, had just bought the house in a white neighborhood; when the mob stoned his house, some men in the house returned fire with guns, killing a white neighbor. The 11 men in the house were charged with murder.]

He got them acquitted in an amazing trial that basically put down in law something we take for granted today—that if we believe a person has the right to defend his home, then African Americans have that right, too. Darrow was a founding attorney for the NAACP, and this was a big case for the NAACP. So that’s how he chose to invest all the fame and potential riches he could have had after his triumph in Dayton, Tennessee.