Fans of The Wire would recognize these cranes from the second season, a rumination on the decline of the working class, set at a stevedores’ union. The first season focused tightly on a wiretap investigation of a major drug organization, as if it were a police procedural. But the addition of the union revealed Simon’s true intent: he was building a city. By the end of season two, he had explored the criminal-justice system, the drug organizations, and the port. The third season added city hall, the churches, and the public-health sector. The fourth season added the school system, academia, nonprofits, and the inner-city family.

Simon was writing a televised novel, and a big one. Innumerable subplots came and went, and main characters disappeared from the show for several episodes at a time. Nothing ever resolved itself in an hour, and there were no good guys or bad guys. All were individuals constrained by their institutions, driven to compromise between conscience, greed, and ambition. Facets of their characters emerged slowly over time. They spoke in the sometimes-unintelligible vernaculars of their subcultures. All of this made unprecedented demands on viewers and provided an immense reward to those who stuck around. A righteous anger at the failure of our social institutions drives The Wire, but the passionate ideas that fuel it are hidden several layers down.

In early September, I visited Simon’s office in Canton. The crew had just wrapped filming on the final episode, and the lobby was cluttered with boxes and plastic-wrapped wardrobe. Simon arrived wearing a black-and-white Hawaiian shirt and Ray-Bans pushed back over his bald head. He took coffee orders from his staff, and we drove to a nearby Starbucks. Mardi Gras beads dangled from Simon’s rearview mirror, and Liam Clancy and Thelonious Monk played on the stereo.

This was Simon at ease. He has a great sense of humor and loves a good yarn. But when we sat down at a conference table to talk about his career at the Sun, Simon was taut and focused, sometimes twisting a paper clip or drawing perfect 3-D boxes on a legal pad. He is still passionate about journalism, and when his frustrations surface he uncorks a blue streak worthy of his fictionalized detectives and drug dealers.

When the Sun hired Simon immediately out of college, he didn’t know Baltimore at all, and the cop beat would not have been his choice, but he worked his tail off. “I filed three hundred bylines in my first year,” Simon says. And though he was green, his colleagues found him fully formed as a reporter and a writer. “He was writing about the sociology of the city through the prism of the cop beat and the criminal-justice system,” says Rebecca Corbett, his first editor, now an editor in the Washington bureau of The New York Times. “And he fairly uniquely looked at the people who we tend to view just as victims or bad guys, and looked at these neighborhoods as real places that we had better understand.”

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.

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.