Well, there is no true answer. They are pretty much amalgams of everyone, but some definite likenesses can be pinned on some people. Included here, is a discussion sent to me by Alan Sepinwall.
Here's a little scorecard of how the nine original characters match up to the real things. Note, however, that even if a character is nearly identical to the way his counterpart appeared in the book, that doesn't mean that they're identical to the real person, as Simon didn't get to see every facet of every detective, or, in some cases, chose to only concentrate on certain aspects. For instance, a Baltimore Homicide detective who posts occasionally to alt.tv.homicide commented that the only thing that Frank Pembleton and his real-life "counterpart" Harry Edgerton have in common is that "they're both males and they're both black. That's it." So, let the reader beware...
Lt. Al "Gee" Giardello & Lt. Gary "Dee" D'Addario
Their names and nicknames are incredibly similar, as is their laissez-faire command style. Dee (or LTD, depending on whom you ask) is one of a small number of white Italians still in a power position in the department, whereas Gee (who is a Black Sicilian) is part of the department's new black power enclave. Since Dee is not as major a factor in the book as Gee is on the show, it is tough to make many other comparisons, although they both overwhelmingly have the unswerving loyalty of their subordinates, while being continually at odds with the upper levels of the department.
Stan "Big Man" Bolander and Donald "Big Man" Worden
Bolander, being referred to as the Big Man because of his weight, is closely related to Donald Worden, who is truly a big man - 6 feet, 5 inches tall, 240 pounds. He is also held in awe by virtually everyone in the department; author David Simon continually refers to him as "the last natural police detective in America." Worden's investigative skills are of mythical proportions, while his memory is of legendary ability. In the early episodes, Stan Bolander was portrayed in much the same way, but after a while, his defining characteristic became his increasing dissatisfaction with the path he'd chosen for his life, including the realization that he hates his job, a thought that would be anathema to Worden.
John Munch and Jay Landsman (and Dave Brown)
While both Munch and Landsman are the comedians of the squad, they are both caring and sensitive. The humor that they exude is used as a shield against the horrors that they see every day. They're also ferocious in the Box, screaming at suspects and witnesses all night long. Landsman commands more respect than Munch does, in part because he's a sergeant and in part because whereas Munch was always overshadowed by the Big Man, while Landsman casts his own shadows.
Munch also owes a bit to perennial Worden whipping boy Dave Brown; in the early episodes, Bolander continually tormented Munch for not being a committed Homicide detective, much like Worden did to Brown. However, as Bolander's character moved further away from Worden's, this kind of abuse (like forcing Munch to give him a quarter as tribute to Bolander's 25 years on the force) was, for the most part, dropped.
Harry Edgerton and Frank Pembleton
Both are well-educated black transplants from New York who prefer to work alone and who are considered outsiders within the Homicide squad, despite the fact that they're both among the best investigators out there. Both are ridiculed for their pink polo ties and fondness for the music of Emmylou Harris. The two characters shared more similarities in the first two seasons, but the attempts to turn Pembleton into Super cop have created quite a bit of divergence - all the material about Frank's crisis of faith, for instance, has absolutely nothing to do with Edgerton.
Tim Bayliss and Tom Pellegrini
Bayliss shares a bit in common with Pellegrini: both spent time on the QRT (Quick Response Team), the parlayed a stint as the mayor's chauffeur into a ticket into Homicide. In addition, the Adena Watson case that threatened to overwhelm Bayliss is a very clear copy of the murder of Latonya Wallace, which practically put Pellegrini in the hospital from exhaustion. However, Bayliss is far more impulsive and emotional than Pellegrini, and has the added baggage of having been on his first day on the job when he was saddled with Adena Watson (Pellegrini was already a two-year vet when he got his version of the white whale).
Kay Howard and Rich Garvey (and Bertina Silver)
Despite the fact that neither one is considered the best investigator or interrogator on their respective squads, both Garvey and Howard seem to have been touched by God - no matter how much of a stone cold whodunit a case may seem, both Howard's and Garvey's hands can close the case. In the year that David Simon was following around the Homicide detectives, Garvey went through a string of ten consecutive clearances. Similarly, at the start of the TV series, Kay was always worried about her perfect streak being ruined.
Kate's only real connection to Bertina "Bert" Silver (an extremely minor character in the book) is that they're both the only female detectives in an all-male environment.
Beau Felton and Donald Kincaid
This is a tenuous comparison, that really only rides on one thing ... their intense dislike of Pembleton/Edgerton. So much, in fact, that in the first episodes of Homicide:LOTS, Felton had been reciting virtually all of Kincaid's anti-Edgerton cracks (in reference to Pembleton) from the book, that it is impossible to not draw a parallel between the two of them. Other than that, they are not very similar. Kincaid is a veteran on the squad, looking forward to retirement, while Felton is a young man barely ten years into his service with the department.
Steve Crosetti and Terry McLarney
McLarney, while never being a fanatic of Abraham Lincoln's assassination, bares a remarkable similarity with Crosetti. Both were former sergeants and veteran investigators, both did not quite get the respect that they deserved, largely because Worden (for McLarney) and Bolander (for Crosetti) have been around longer than they have. Both men were shot in the line of duty before joining Homicide and take their scars very seriously. Both also had to endure the tragedy of having their proteges shot and blinded in the line of duty. In addition, both receive ribbing about their ancestry - Dave Brown refers to the Irish McLarney as a "potato head" and Meldrick Lewis often derided the Italian Crosetti as a "salami head."
Crosetti was killed off at the start of the third season, which is when most of the characters really started deviating from their real-life inspirations, so he's the only one who remains close to the spirit of the original.
Meldrick Lewis & Donald Waltemeyer
This is one of the less obvious pairings, since A)Meldrick is black and Waltemeyer is white, B)Waltemeyer is one of the more minor characters in the book, and C)Meldrick's personality wasn't really fleshed out until the third season. However, there are two things that connect the two. First, Waltemeyer and Lewis both wound up investigating a series of murders by a "black widow" who married men, then killed them for the insurance money. Second, one of the few things we learn about Waltemeyer's personality is that he has a "patrollman's mentality," in that he's often impatient with the meticulous nature of being a Homicide detective, as is the often impulsive Lewis.
Alan Sepinwall (firstname.lastname@example.org)
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