Simon began to hit his stride after a five-part series in 1987 on notorious drug lord “Little Melvin” Williams. (Williams, five years out of prison, now plays a deacon on The Wire.) Then he asked Police Commissioner Edward Tilghman if he could spend a year shadowing the homicide department for a book. Surprisingly, Tilghman said yes, as did Simon’s editors, and in 1988 Simon took fifteen months off to report Homicide: A Year on the Killing Streets, published by Houghton Mifflin in 1991.

That same year, The Times Mirror Company, which had bought the Sun from the A. S. Abell Co. in 1986, lured John Carroll away from the Lexington Herald-Leader to edit the Sun. “The paper had problems that needed to be solved,” Simon says, and he was excited to see Carroll come on board. Carroll’s stellar reputation as a protégé of Gene Roberts at The Philadelphia Inquirer had preceded him, and Simon believed that the Sun would have the ingredients—Sun veterans, talented new hires, new leadership, and flush finances—to produce first-class journalism.

In 1993, Simon took a second book leave, this time to observe the war on drugs from one of the roughest neighborhoods in Baltimore for The Corner: A Year in the Life of an Inner-City Neighborhood, which he co-wrote with retired Baltimore homicide detective and current Wire co-producer Ed Burns. Shortly after Simon left, Carroll brought in Bill Marimow, a colleague from the Inquirer, as metro editor at the Sun, and Marimow quickly rose to managing editor. Out on the streets, Simon was developing a fuller vision of where he wanted to go as a journalist. The cops and crime beat, it turned out, was the best thing that ever happened to him, and he thought that his two year-long, book-reporting excursions had revealed deeper truths about why the city was the way it was. He felt ready to address its complexity.

Simon returned briefly from book leave to write a four-part series called “Crisis in Blue” for the Sun, about a dysfunctional police department. At the time, Baltimore had registered a record number of homicides the previous year, and a new police commissioner was about to take the helm of a department in decline. It was a sprawling subject, but Simon found the numbers to focus and quantify it: crime was up 37 percent, yet arrest rates were down for violent crime because the felony divisions had been depleted to fill the ranks at homicide. Simon captured the qualitative nuance through his deep reservoir of sources in the department and on the street: robbery victims who never heard back from the police; a junkie rotating from the corner to the courthouse five times in six months only to receive a verdict of probation before judgment; detectives who advocated for a unit to target violent drug rings only to get transferred because they had deviated from the street-level arrest orthodoxy. Simon had the historical grasp to show the progression from a well-respected department full of disciplined Vietnam veterans through twenty years of “planned attrition” to a disorganized, underpaid force that was moonlighting to pay the bills. His sociological eye caught the systemic flaws in a futile drug war: a patrol cop collecting court pay for six cases in one day while his collars walked out with probation; the irony of the fact that neighborhood activists’ demands to clean up the corners led to mass arrests of users while the repeat offenders who brought the drugs to town and did the murders walked free.

For an exposé of a failing police department, “Crisis in Blue” is remarkably free of villains. The reader finds not just individual actors making bad decisions, but a fatally flawed system that those actors struggle to accommodate. Reporting from the front lines of the war on drugs taught Simon everything he needed to know about that system. “How can you report on a place like Baltimore, where one of every two black males is without work,” he said, “and in any way regard the economic structure as being viable?”

A ‘Rule for the New Millennium’

Lawrence Lanahan is formerly an analyst with American Institutes for Research in Washington, D.C. He lived in Baltimore for five years and is now a freelance journalist based in Brooklyn. The fifth season of The Wire premiered January 6, 2008 on HBO.