Don Winslow

• Born: October 31, 1953
• Place of Birth: New York, New York

TYPES OF PLOT: Private investigator; comedy caper; thriller; inverted; espionage

PRINCIPAL SERIES: Neal Carey, 1991-1996; The Cartel, 2005-2019; Boone Daniels, 2008-2009; Savage, 2010-2012; Frank Decker, 2014-2016; Danny Ryan, 2022-2024

Contribution

Like many writers, Don Winslow has converted significant autobiographical events into fiction. Winslow’s life encompasses considerable occupational and geographical territory. His interesting, if checkered, earlier career has provided a wealth of material related to crimes of domestic and international scope, has given him an expanded worldview, and has lent him a dry, sardonic wit that informs much of his work. His stints as an undercover agent, private investigator, hostage simulator, fraud and arson analyst, safari leader, and freelance consultant have brought him into contact with a wide range of criminal and law enforcement types that he delineates with unerring accuracy, and he writes about the work involved with unquestioned authority.

Winslow has not become a household name but has elicited critical acclaim for his novels and collaborative nonfictional work. His first novel, A Cool Breeze on the Underground (1991), introduced private investigator Neal Carey, and it gained an Edgar Award nomination. California Fire and Life (1999) garnered a Shamus Award for Best Novel. The Power of the Dog (2004) was nominated for a Macavity Award and Deadly Pleasure magazine’s Barry Award. His nonfictional collaborative effort, Looking for a Hero: Staff Sergeant Ronnie Hooper and the Vietnam War (2004), attracted considerable attention for its unflinching portrait of the turbulent life of a real soldier. His The Death and Life of Bobby Z (1997) was made into a feature film in 2007.

Biography

Don Winslow was born on October 31, 1953, in New York City, the son of US Navy noncommissioned officer Don Winslow, Sr., and librarian Ottis Schevrmann Winslow. Because of his father’s occupation, Winslow moved frequently as a child. He grew up primarily in Warwick, near Providence, and South Kingstown, Rhode Island. As a young child, he performed in theater and voiced radio commercials.

IIn the early 1970s, Winslow attended the University of Nebraska-Lincoln, majoring first in journalism and later in African history, and directed a theater company. During his junior year in college, he worked as a researcher at the University of Cape Town, South Africa, and freelanced as a newspaper reporter. Winslow also surreptitiously brought in funds for TEACH—an educational organization in Soweto banned by the apartheid government—an action that led to his arrest and deportation. He traveled around southern Africa until returning home to complete his Bachelor’s degree.

Following graduation, Winslow directed a theater company for two years, then moved to rural Idaho, where he herded cattle. Winslow relocated to New York City, where he managed movie theaters for three years. He then worked at a detective agency as an undercover operative investigating a theft at a chain of theaters. He was also engaged in operations in London and Amsterdam for the same agency. The work led to employment with the Institute for International Studies, where—through simulated kidnappings—he helped train representatives from the national government, law enforcement, and the media in terrorist situations and hostage negotiations.

Winslow returned to school, earning a Master’s degree in military history while freelancing as a private investigator. He aspired to join the US Foreign Service but instead joined a firm specializing in safaris and spent five years planning, selling, and leading treks into China and Kenya. In Kenya in 1985, he met and proposed to his wife, designer Jean Enstrom; the couple had a son, Thomas, born in 1989. After a term designing overseas educational programs for high school students, Winslow was briefly employed with Forensic Anthropology as an arson and fraud analyst. When the company folded, he continued working as a freelance investigator and consultant to law firms, assisting witnesses in preparing to give testimony.

Drawing on his colorful history for inspiration, Winslow published his first novel, A Cool Breeze on the Underground, in 1991. The first in a series of novels centering on private investigator Neal Carey, it was nominated for an Edgar Award. Later nonseries novels have garnered Winslow similar critical acclaim and comparisons to Elmore Leonard and Carl Hiaasen for his unique amalgamation of hard-boiled action and humor. He has also written short stories, stage plays, screenplays, and television scripts, and he has collaborated on a nonfictional book about a troubled American Medal of Honor winner, Looking for a Hero: Staff Sergeant Ronnie Hooper and the Vietnam War. By the mid-2020s, Winslow had added several more stand-alone novels to his catalog and five new series of books.

Analysis

As crucial as Don Winslow’s convoluted plots are to his work, his novels are, first and foremost, studies of intriguing characters from both sides of the law and all gradations in between. His well-trained (and somewhat jaundiced) eye can spot telling physical clues that help reveal personality, and his ear catches subtle nuances and rhythms of conversation. Winslow is adept at portraying a character’s angst and giving voice to innermost thoughts, often tinged with terse, ironic, self-deprecating understatement. Even the best characters are severely flawed, and the worst have redeeming features.

Winslow’s early novels (beginning with A Cool Breeze on the Underground) all concern freelance private investigator Neal Carey and the bizarre cases he is enlisted to undertake. These are told in the third person rather than the usual first person used for detective novels, allowing the author to jump from character to character as necessary to present information the protagonist alone would not know, thus increasing suspense. Though violence plays a role in these books, it takes a backseat to the generally lighthearted presentation of madcap adventures fraught with multiple humorous complications and of an assortment of types of usually believable people who either want something or want to prevent others from achieving something. Winslow’s growing maturity as a writer is evident from book to book, as characters become more sharply drawn, dialogue grows terser, and the prose style becomes leaner—all of which combine to make pacing more consistent, resulting in increased tension throughout.

Later nonseries novels take a darker tone while keeping Winslow’s strengths—character portrayal, dialogue, and twisty plots—intact. Protagonists in these novels, unlike Neal Carey, who, though laid-back is nonetheless heroic, are more complex and contradictory. For example, Walter Withers, an alcoholic private eye of questionable morality in A Long Walk Up the Water Slide (1994), commits various dubious acts while battling both the Central Intelligence Agency (CIA) and the Komitet Gosudarstvennoy Bezopasnosti (KGB) in the course of protecting an ambitious politician in Isle of Joy (1996), a thriller set in the 1950s against the paranoia of the Cold War. The central character in The Death and Life of Bobby Z (1997) is born loser Tim Kearney—sentenced to life for killing a member of the Hell’s Angels and surrounded by vengeful imprisoned bikers—who is given the chance to win his freedom by impersonating a missing drug kingpin named Bobby Zacharias (“Bobby Z”). Crack arson investigator Jack Wade from California Fire and Life (1999) lost his job as a police officer for beating a confession out of a felon. Former CIA operative and Drug Enforcement Agency (DEA) agent Art Keller in The Power of the Dog (2005) constantly breaks rules in his pursuit of justice and is especially unconcerned about legal issues in his devotion to the destruction of Mexican drug lord Tio Barrea, a former police officer whose ascent Keller unwittingly aided by eliminating his rivals. Protagonist Frank Machianno, in The Winter of Frankie Machine (2006), is a never-miss mob hit man, now retired and running a bait shop in Southern California, who is reluctantly lured back into his former profession. Additional stand-alone novels published by Winslow in the twenty-first century include Satori (2011), Vengeance (2014), and The Force (2017).

Though another Winslow trademark, humor, is not absent in his tales of espionage, drug deals gone wrong, horrible deaths by immolation, and wholesale mob assassinations, the laughs are somewhat downplayed because they would be inappropriate given the more serious nature of the subject matter. People lie and cheat and die and kill—such things are not the usual stuff of comedy, except for the morbidly inclined. Thus, Winslow transforms the ridiculous to the sublime in the form of wry and truthful observations concerning human nature, and plot complications farfetched enough to be believable—operating on the “truth is stranger than fiction” principle—provoke sad smiles of recognition rather than hearty laughs. Although Winslow shows violence close up and in Technicolor, he does not glorify it. Graphic scenes are presented matter-of-factly as the logical progression of evil deeds that cannot help but adversely affect the good, the bad, and the in-between alike.

A Long Walk Up the Water Slide

The fourth novel in the Neal Carey mystery series, A Long Walk Up the Water Slide, begins as a routine assignment for Neal and quickly deteriorates into a farcical romp, perhaps inspired by the Jimmy Swaggert and Jim Bakker sex scandals. Brooklyn-born Polly Paget, a secretary for the wholesome television show the Jack and Candy Family Hour, has been having an affair with Jackson “Jack” Landis, costar of the show and founder, president, and majority owner of the Family Cable Network. Polly publicly claims that after ending their affair, Jack raped her, but her heavy New York accent and bimbo-like appearance prevent her from presenting herself credibly before the media. Therefore, Neal is to hide her at his Nevada home while, like Henry Higgins, he grooms her linguistically so she will be more believable and more likely to be awarded a large settlement.

There are many forces at work throughout the story because, in addition to the fate of the network in the wake of a scandal, there is much at stake, including Candyland, a planned family resort under construction outside San Antonio, Texas, featuring condominiums and a gigantic water slide. Antagonists include tabloid reporters eager for a scoop, an alcoholic private detective sent by a pornography publisher to offer Polly a small fortune to appear in a magazine spread, mobsters and their minions raking off money from the construction of Candyland, lawyers for various factions within the network who have their own agendas, and a professional assassin sent to make sure Polly does not survive to jeopardize the whole television empire.

A Long Walk Up the Water Slide is a complex, fast-paced, satirical thriller told in snapshot scenes from divergent viewpoints across the whole cast of participants. Winslow performs a masterful balancing act, veering from slapstick to extreme violence but never losing sight of his objective, demonstrating that significant issues consist of small acts. The novel has a manic feel, with numerous plot reversals and unexpected twists. Characters often begin as stereotypes and reveal hidden depths that make them fully rounded. Dialogue, a particular Winslow strength, is full of insight and irony, sparked throughout with humorous throwaway lines that provide comic relief in tense situations.

While Drowning in the Desert

The fifth Neal Carey novel, While Drowning in the Desert (1996), presents the detective with a seemingly straightforward errand: elderly Nathan Silverstein, supposedly in the first stages of Alzheimer’s, has wandered away from his California condominium. He is currently in Las Vegas, and Carey’s task is to collect him and fly with him back to his home.

As usual, the simple job becomes complicated. Nathan Silverstein is an old-time stand-up comedian known in his Catskills heyday as Natty Silver. Far from having Alzheimer’s, Natty is still sharp: He has an inexhaustible supply of jokes and one-liners that he is not shy about airing. The octogenarian also has an active libido, which comes into play when he runs into an old flame in Las Vegas, a former showgirl and current piano bar chanteuse, Hope White. Natty refuses to fly, so Neal must rent a car to drive to California. During the trip, it is revealed that Natty witnessed a crime, so he fled. Reluctant to return to the crime scene, Natty steals Neal’s rental car and sets off across the desert, pursued by the criminals who wish to eliminate the only witness to their misdeeds while Neal scrambles to catch up.

A fast-paced page-turner with a relatively small cast of well-drawn characters, the novel features hallmarks of Winslow’s popular series: sparkling dialogue, wry observations about life in general and aging in particular, and gently satirical humor.

Principal Series Characters:

• Neal Carey is a part-time, reluctant investigator for a confidential organization known as Friends of the Family, operated by the Bank in Providence, Rhode Island, which provides clandestine services for wealthy depositors. Neal, the son of a heroin-addicted prostitute, never knew his father (one of his mother’s customers) and was orphaned at the age of twelve. Neal seldom uses guns because he is a lousy shot and even more inept than a fistfighter. A frustrated scholar with a peculiar sense of humor and a jaded attitude, Neal transferred credits from Columbia University to Nevada, where he lives in the desert village of Austin.
• Joe Graham is Neal’s adopted father: They met when Neal attempted to pick Joe’s pocket, and after that, Joe raised the youngster, teaching him tricks of the investigative trade, such as lock picking, surveillance, and tracing missing persons. He also serves as Neal’s boss, handing out assignments for Friends of the Family. A short, almost dwarfish man with an artificial hand, Joe is not afraid to mix it up with the bad guys with whom his son’s assignments invariably bring him in contact, and often, he has to bail the younger man out of trouble.
• Karen Hawley is an occasional elementary schoolteacher, an attractive, no-nonsense woman, and Neal’s live-in girlfriend. She often becomes unwittingly entangled in Neal’s assignments. Keenly aware of her biological clock, Karen wants to marry Neal and have children.

Although the Neal Carey series ended, Winslow continued to produce literary series that gripped his reading audiences. Winslow’s additional series include: The Cartel (2005-2019), Boone Daniels (2008-2009), Savage (2010-2012), Frank Decker (2014-2016), and Danny Ryan (2022-2024). Winslow stated that the final installment in the Danny Ryan series, City in Ruins (2024), may be his final novel. The books in these series have been finalists for several literary awards. Winslow remains open about sharing his political views in the traditional media and on social media. 

Bibliography

Italie, Hillel. “With Some Laughs, Some Stories, Some Tears, Don Winslow Begins What he Calls his Final Book Tour.” AP News, 2 Apr. 2024, apnews.com/article/don-winslow-last-book-city-ruins-347d8ad247cd4e7775917830059b1399. Accessed 23 July 2024.

Mobilio, Albert. “An Insurance-Business Thriller? Actually, Yes.” Review of California Fire and Life, by Don Winslow. Fortune, vol. 144, no. 4, 16 Aug. 1999, p. 44.

Publishers Weekly. Review of A Cool Breeze on the Underground, by Don Winslow. vol. 238, no. 2, 11 Jan. 1991, p. 94.

Publishers Weekly. Review of The Trail to Buddha’s Mirror, by Don Winslow. vol. 239, no. 6, 27 Jan. 1992, p. 91.

Publishers Weekly. Review of Way Down on the High Lonely, by Don Winslow. vol. 240, no. 40, 4 Oct. 1993, p. 67.

Ruland, Jim. “Why Don Winslow Is Retiring from Writing after 'City in Ruins.'” Los Angeles Times, 1 Apr. 2024, www.latimes.com/entertainment-arts/books/story/2024-04-02/don-winslow-retiring-city-in-ruins-last-novel. Accessed 23 July 2024.

Woods, Sean. “Don Winslow Trades Writing Novels for Political Activism Against Trump.” Rolling Stone, 2 Apr. 2024, www.rollingstone.com/culture/culture-features/don-winslow-last-novel-political-activism-trump-1234997655. Accessed 23 July 2024.