Winters was first known as the author of the 2009
New York Times bestseller
Sense and Sensibility and Sea Monsters. In June 2010,
Android Karenina was published by
Quirk Books. A young adult novel,
The Secret Life of Ms. Finkleman, was published by HarperCollins in September 2010.
Finkleman was nominated for an Edgar Award by the Mystery Writers of America in January 2011. In 2011, Winters published a second book in the Ms. Finkleman series, titled
The Mystery of the Missing Everything, and
Bedbugs, a horror novel for adults. Winters has also written numerous books in the
Worst-Case Scenario Series. In 2012, Winters published
The Last Policeman, the first in a trilogy of detective novels set in a pre-apocalyptic United States; that book won the Edgar Award from the Mystery Writers of America in the category Best Paperback Original; was an Amazon Best Book of 2012; and was nominated for the Macavity Award for Best Mystery by Mystery Readers International. The second novel in the Last Policeman trilogy,
Countdown City, was published in July 2013; it won the 2014
Philip K. Dick Award for Distinguished Science Fiction. The third book in the Policeman series,
World of Trouble, was published in July 2014. It was nominated for the Edgar Award in the category of Best Paperback Original Winters's work for the theater includes the Off-Broadway musical
Slut, the children's musicals
The Midnight Ride of Paul Revere,
Uncle Pirate, and
A (Tooth) Fairy Tale and the
Neil Sedaka juke-box musical,
Breaking Up Is Hard to Do. Winters's novel
Underground Airlines was published by Mulholland Books in July 2016. It is an
alternate history book, set in a present-day alternate universe in which the
American Civil War never occurred, with human
chattel slavery continuing to be practiced legally in four U.S. states as a result. In the book, the main character, a former slave and bounty hunter working for the U.S. government, attempts to infiltrate an
abolitionist organization known as the "Underground Airlines" (a reference to the historical
Underground Railroad). The book was an Indie Next pick for July 2016 and a
New York Times bestseller. The book won the 2016
Sidewise Award for Alternate History. His novel
Golden State was published by Mulholland Books in January 2019. The novel imagines an
alternate history version of Southern California in which objective reality is fetishized and protected above all things, and lying is the greatest crime imaginable. Winters has said the book was inspired by the rise of
alternative facts and in particular by the argument about the crowd size at the 2017 presidential inauguration.
Golden State was an Indie Next pick for January 2019 and a Book of the Month Club selection. Writing in the
San Francisco Chronicle, Michael Berry called the novel "smart, intricate and propulsive" and "proof that Winters deserves our continued attention as one of crime fiction’s most inventive practitioners." In 2021 Winters published
The Quiet Boy. Reviewing
The Quiet Boy in the
New York Times, Sarah Lyall wrote "Winters is such a fine writer that by the time he asks you to suspend your disbelief, you’ll follow him anywhere." His thriller
Big Time centering on two average women caught up in the world of corporate espionage, arrived March 2024. Critics praised
Big Time as a "fast-paced and thought-provoking speculative thriller with well-drawn and relatable characters" and "jaw-dropping plot twists." Winters has been active in television since 2016, developing pilots and staffing on shows such as
Legion and the Apple limited series
Manhunt. In 2022 it was announced that Winters was creating a show based on the
Jeffery Deaver novel
The Never Game, later retitled
Tracker for
CBS. The procedural, starring
Justin Hartley of
This Is Us and directed by
Ken Olin, was picked up to series and premiered after Super Bowl LVIII in February 2024. ==Personal life==