New York Ruthless Books in Order
Part ofSadie Kincaid Books in OrderFollow the New York Ruthless books by Sadie Kincaid in order, with short summaries, reverse‑harem reading order help and background on Jessie, the Ryan brothers and their Irish mafia empire.
Last updated: December 22, 2025
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Publication Order
16 books
A Ryan Regret
by Sadie Kincaid
2024
A Ryan Regret explores what happens when one of the Ryans makes a mistake big enough to shake their carefully built family. Hurt feelings, heartfelt apologies and scorching make-up scenes drive this emotional, high-angst follow-up novella.
Another Ryan Christmas
by Sadie Kincaid
2023
Another Ryan Christmas returns to Jessie and her four husbands for a later holiday season, mixing cozy traditions with over-the-top gifts, family cameos and very explicit alone time. It’s a warm, spicy check-in for New York Ruthless fans.
A Ryan Review
by Sadie Kincaid
2023
In A Ryan Review, the extended Ryan family looks back over their wild journey so far—celebrating wins, teasing each other and revisiting favourite scenes. It reads like an extra-long epilogue packed with humour, heat and fan-service moments.
A Ryan Revelation
by Sadie Kincaid
2023
A Ryan Revelation brings buried truths to the surface, forcing Jessie and each Ryan brother to question what they thought they knew about their pasts. The answers are messy, emotional and, of course, punctuated by plenty of filthy celebration.
A Ryan Recon
by Sadie Kincaid
2023
A Ryan Recon offers a glimpse of the Ryans on a mission, blending their usual filthy banter with genuine suspense. Jessie joins her husbands for high-stakes reconnaissance that blurs the line between business, protection and pure indulgence.
Ryan Retribution
by Sadie Kincaid
2022
Jessie’s secrets and the Ryans’ enemies collide in the third New York Ruthless book. The family’s empire is under attack from all sides, and every choice pushes their unconventional relationship closer to breaking—or to becoming unshakeable.
Ryan Renewed
by Sadie Kincaid
2022
In Ryan Renewed, Jessie and the Ryans face a fresh threat after the events of Ryan Reign. This darker, later-in-life chapter tests their marriage, their empire and the promises they made to each other.
Ryan Reign
by Sadie Kincaid
2022
With blood spilled and lines crossed, the final main New York Ruthless novel brings Jessie and her four Ryans to their endgame. Old debts are paid, new futures are claimed, and their hard-won family either shatters or finally reigns.
Ryan Redemption
by Sadie Kincaid
2022
Book two of New York Ruthless picks up after Ryan Rule’s cliffhanger, with Jessie and the Ryan brothers reeling from betrayal. As enemies close in and feelings deepen, they’re forced to choose between vengeance, survival and the family they’re building.
A Ryan Rewind
by Sadie Kincaid
2022
Reliving the early days of their relationship, A Ryan Rewind lets Jessie and the Ryans look back at the moments that changed everything. This novella fills in missing scenes with extra heat, humour and a sweeter glimpse of their beginnings.
A Ryan Restraint
by Sadie Kincaid
2022
In A Ryan Restraint, Jessie and the Ryans lean hard into their kink, exploring new boundaries of control, patience and pleasure. This steamy vignette focuses less on plot and more on the dirty-talking, dominant dynamics fans love.
A Ryan Reckoning
by Sadie Kincaid
2022
In A Ryan Reckoning, Jessie and her four Irish mafia husbands are forced to confront the fallout of past choices. This New York Ruthless novella mixes domestic chaos, sharp banter and scorching scenes with a reminder that love has consequences.
A Ryan New Year
by Sadie Kincaid
2022
New Year’s Eve with the Ryans is never quiet. This novella follows Jessie and her husbands through celebrations, resolutions and one more round of danger, wrapping their year up with explosive heat and a promise of more to come.
A Ryan Halloween
by Sadie Kincaid
2022
Set around Halloween, this New York Ruthless short throws Jessie and her four husbands into costumes, parties and a fresh dose of trouble. Tricks, treats and possessive Irish mobsters combine for a fast, filthy seasonal read.
A Ryan Christmas
by Sadie Kincaid
2022
Five days before Christmas, Jessie Ryan has a string of sinful surprises planned for her four possessive Irish mafia husbands. A Ryan Christmas delivers festive spice, a touch of drama and a warm check-in with the New York Ruthless family.
Ryan Rule
by Sadie Kincaid
2021
Flame-haired hacker Jessie Heaton works for the Russians and is one job away from getting what she wants when the Ryan brothers—untouchable Irish mafia kings of New York—intercept her. Their collision sparks a dangerous, addictive reverse-harem romance.
Series background & context
New York Ruthless shifts the action to Manhattan’s Irish mafia, where the Ryan brothers run their organisation with the kind of single-minded loyalty that leaves no room for outsiders. Then Jessie Heaton barrels into their lives—a flame-haired hacker working for the Russians, with her own agenda and a past she can’t outrun.
She’s the hurricane that blows their carefully ordered world apart.
Ryan Rule launches the series as Jessie finds herself trapped between dangerous employers and a family of men who are used to getting exactly what they want. Each of the main novels—Ryan Redemption, Ryan Retribution and Ryan Reign—builds on that collision. Secrets come to light, alliances shift and the line between captor and protector blurs as Jessie grows closer to each brother.
The series is unapologetically why-choose: Jessie doesn’t have to pick one Ryan, and the emotional heart of the books lies in watching five people figure out how to build something that looks like a life together. Expect cliffhangers, intense jealousy, fierce devotion and sex scenes that lean heavily into praise, punishment and power games.
Ryan Renewed and the run of shorter stories—holiday specials, slices of domestic chaos and extra moments of danger—act as extended epilogues to the main arc. They revisit Jessie and the Ryans once the dust has settled, showing what happily-ever-after looks like when your husbands are still running a ruthless criminal empire.
Because the Ryans operate in a brutal world, these books come with plenty of trigger warnings: violence, kidnapping, coercion and trauma all feature alongside the romance. Kincaid never pretends this is a safe universe, but she does give her characters room to grow, heal and claim something softer in the middle of all that sharpness.
You can jump in here, but reading the novels in order is strongly recommended.
While the series stands on its own, it’s threaded through with nods to the other Ruthless books—Montoya lieutenants popping up in New York, mentions of London power players and the sense that all of these families are part of the same bloody chessboard.
Edited by
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