Below is the complete list of Sadie Kincaid’s New York Ruthless books in order. For this series, the chronological reading order is the same as the order of publication.
Publication Order of New York Ruthless Books
- Ryan Rule (2021)
Ryan Rule was published in 2021 and is listed as book #1 in the New York Ruthless series. - Ryan Redemption (2022)
Published in 2022, Ryan Redemption is listed as book #2 in the New York Ruthless series. - Ryan Retribution (2022)
Ryan Retribution is a 2022 release and appears as book #3 in the New York Ruthless series. - Ryan Reign (2022)
In the New York Ruthless series, Ryan Reign is book #4 and was published in 2022. - Ryan Renewed (2022)
Ryan Renewed was first published in 2022; within the New York Ruthless series, it is listed as book #5. - A Ryan Reckoning (2022)
A Ryan Reckoning was published in 2022 and is listed as book #6 in the New York Ruthless series. - A Ryan Rewind (2022)
Published in 2022, A Ryan Rewind is listed as book #7 in the New York Ruthless series. - A Ryan Halloween (2022)
A Ryan Halloween is a 2022 release and appears as book #8 in the New York Ruthless series. - A Ryan Christmas (2022)
In the New York Ruthless series, A Ryan Christmas is book #9 and was published in 2022. - A Ryan Restraint (2022)
A Ryan Restraint was first published in 2022; within the New York Ruthless series, it is listed as book #10. - A Ryan New Year (2022)
A Ryan New Year was published in 2022 and is listed as book #11 in the New York Ruthless series. - A Ryan Revelation (2023)
Published in 2023, A Ryan Revelation is listed as book #12 in the New York Ruthless series. - A Ryan Recon (2023)
A Ryan Recon is a 2023 release and appears as book #13 in the New York Ruthless series. - A Ryan Review (2023)
In the New York Ruthless series, A Ryan Review is book #14 and was published in 2023. - Another Ryan Christmas (2023)
Another Ryan Christmas was first published in 2023; within the New York Ruthless series, it is listed as book #15. - A Ryan Regret (2024)
A Ryan Regret was published in 2024 and is listed as book #16 in the New York Ruthless series.
About New York Ruthless
Sadie Kincaid’s New York Ruthless series is the dark mafia romance sequence that brought many readers into her wider Ruthless world. The series begins with Ryan Rule and follows Jessie Heaton and the Ryan brothers through a high-stakes reverse-harem romance shaped by trauma, protection, revenge, family loyalty, and the violent power struggles surrounding New York’s criminal underworld. It is one of Kincaid’s defining series, not only because of its popularity, but because it establishes the emotional and stylistic pattern that later branches such as Chicago Ruthless, L.A. Ruthless, London Ruthless, and Manhattan Ruthless continue in different forms.
Jessie Heaton is the central figure of the series. She is a skilled hacker, fiercely independent, and used to surviving without relying on anyone. Her life changes when she becomes entangled with the Ryan brothers: Shane, Conor, Liam, and Mikey. Each brother brings a different kind of danger, protectiveness, and emotional complication into Jessie’s life, but the series does not treat them as interchangeable romantic figures. Their personalities, wounds, loyalties, and roles within the family create the structure of the relationship dynamic, while Jessie’s own history and strength keep her from being reduced to someone simply protected by powerful men.
The opening book, Ryan Rule, introduces the Ryan family’s world of wealth, violence, control, and old enemies. Jessie is pulled into that world under dangerous circumstances, and the early tension comes from the collision between her independence and the brothers’ instinct to protect and possess. Kincaid uses the mafia framework to heighten every emotional choice. Trust is not casual here. It can mean safety, betrayal, or surrender, depending on who is offering it and what they expect in return.
As the series continues through books such as Ryan Redemption, Ryan Retribution, and Ryan Reign, the story expands beyond the initial romantic setup into deeper family conflict and unresolved threats. The Ryan brothers’ pasts become increasingly important, especially as enemies and secrets force the family to confront what has been hidden, inherited, or left unfinished. The figure known as the Wolf becomes a major source of danger and fear, pushing the series into darker territory as Jessie and the Ryans are tested by violence, manipulation, and the consequences of earlier choices.
Ryan Renewed gives the series a more settled emotional stage after the core conflict, while A Ryan Recollection gathers shorter connected material that expands the world around the main books. These later pieces matter most for readers who want the fuller emotional texture of Jessie and the Ryans after the central arc has been established. They do not change the identity of the series, but they add extra moments of continuity, intimacy, and family connection.
New York Ruthless is best understood as dark reverse-harem mafia romance rather than crime fiction. The criminal world supplies the danger and power structure, but the emotional focus is Jessie’s bond with the Ryan brothers and the way love becomes tangled with safety, obsession, loyalty, and healing. Kincaid writes this world in heightened terms: the stakes are extreme, the men are morally complicated, and the romance is intense rather than gentle. Its appeal lies in watching a woman who has survived alone become the center of a dangerous family’s devotion, without losing the sharpness that made her powerful in the first place.